Lawyers' Wildest Cases

June 27, 2023 | Carl Wyndham

Lawyers' Wildest Cases

From disastrous interrogations to unbelievably stupid "evidence", these lawyers' wildest trials prove that sometimes, "law and disorder" is a more accurate description of what happens in a courtroom.

1. What A Heel!

In court one morning, the accused wore a pair of very unique custom-made red cowboy boots... that were stolen from the house he was accused of robbing. Yes, he wore them. To court. To plead not guilty. The prosecutor was laughing.

Lawyers Share “I Rest My Case” Moments FactsPxHere

2. The Prescription Writing on the Wall

I was involved in a custody dispute. The dad alleged the mom was doing all sorts of things, and he should have the kid. The dad's attorney grilled the mom about texts she had sent where she was trying to sell prescription pills. She wouldn't admit it. It seemed like the dad's attorney moved on...until he came up with a brilliant trap.

He eventually ended with, "One more question. Where did you get the pills you were selling". Mom responds without thinking, "Oh, my doctor prescribed them".

Instantly Ended a Case factsShutterstock

3. Ableism In Effect

I was the plaintiff in a tribunal suing for wrongful termination. My representative says, “So you terminated him because he was ill"? The employer responds, “Yes”. My representative continues, “And he was ill because he's disabled"? Again, the employer says yes. “So you fired someone for being disabled"? The employer says, “Yes”.

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4. Justice McServed

This woman wanted me to sue Mcdonald's because their employees beat up her son. He was trying to rob the place.

Prisoners Adjusting Outside factsWikimedia Commons, Michael Rivera

5. Snapshots Fired

I had a client once who started his divorce case by representing himself before hiring me to take over. I catch up with what's already gone down by asking my new client what he’s filed with the court. He slides an envelope across the table. I wish I'd never opened it. It’s a multitude of pictures of his overweight wife spread eagle with the camera three feet away showing everything.

Yes, the judge saw. And no, he wasn’t pleased. Apparently, this client had caught his wife sending these pictures to men on the internet.

Janet Leigh factsShutterstock

6. The Customer Is Always Right

This lady got into a minor fender bender with a truck in a casino parking lot. My guy said she parked and went inside the casino for a few hours. At her deposition, she testified that she was so hurt that she went right home and to a hospital. So I asked if she was a frequent visitor of the casino, and if she had a rewards card.

She was happy to tell me she did, and she had gold status and showed me the card. This turned out to be her big mistake. I subpoenaed her rewards card's records, and it showed she was playing slots for hours after the accident.

Lawyers Screwed factsWikipedia

7. I Haven’t Got You, Babe

I used to work in "baby daddy" court as a caseworker. This guy kept telling me, the mother of the child, and anyone who would listen that the baby was NOT his. When they went before the judge, the judge confirmed through DNA testing that he wasn't the dad. The dude turned around and ripped off his jacket. His undershirt said, "NOT THE FATHER"!

Jerry Springer FactsGetty Images

8. Spoiler Alert Will

Two sons of a really wealthy couple go to the family lawyer to have their recently deceased parents' will read out. The lawyer is super nervous because he has known them both since they were children...and he's about the reveal their darkest family secret. One son gets the entire inheritance, while the other gets nothing.

The explanation was that it should be passed through to blood relatives only. So that was the day that son found out he was adopted.

Crazy Wills FactsShutterstock

9. Well, I Guess He Walked Right Into That One...

My lawyer dad had a person come in and claim he couldn't walk because of some "injury" at work. At the time, my dad was skeptical so he hired a psychologist to do an examination on him, and she found out that something COULD be wrong, but she couldn't put her finger on it. Jump to next week, my dad ends up with a video in his hands of the person WALKING down their driveway to take out the trash.

Busted. So my dad called them and told them "Hey come on in, we have a breakthrough in your case, and you can get some money for your injury". So the guy comes to his office, and he leaves him sitting in the lobby for almost an hour because my dad knows this guy is a jerk just trying to get money over nothing (which makes lawyers look bad).

So then my dad calls him into the meeting room and plays the video. The guy walked out.

"I Want To Sue" Case FactsShutterstock

10. No Parting Gift Like One Last Miff

Lawyer here. I thought I'd seen it all, but this vicious will proved me wrong: "To my wife I leave her lover and the knowledge that I was never the fool she thought me. To my son I leave the pleasure of working for a living—for 25 years, he thought the pleasure was all mine". Best diss ever.

Lawyers' Shocking Cases factsShutterstock

11. A Love-Hate Relationship

My client was accused of not leaving this woman alone when she wanted no contact with him. He swore that they were dating, and she'd call the authorities when she got mad. She swore she wanted nothing to do with him. She had a photo on her phone of him sitting on her porch, to prove that he'd come around without her consent.

I asked permission from the judge to look at the photos before and after to get context. Lo and behold, she had hundreds of photos of him. Eating dinner with her, sitting on her couch—even wearing her undergarments. It was a glorious moment.

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12. Salt Of The Earth

Lawyer here. I once amended a will for a doctor in which he disinherited his son by removing everything he had intended to bequeath and replacing it with a "manure spreader”. I didn't ask any questions because changing a will is an easy thing to do. But one day, that doctor will die, and his son will have essentially be told to "eat excrement".

The Weirdest Wills FactsShutterstock

13. Surprises Comes In Twos

My estate planning professor told us about a guy who had two families, neither of which knew about the other until it was time to read the man's will after he passed. This wasn't like a love child/mistress type scenario, both were nuclear multi-kid families. Both families showed up for what had to be one of the most awkward will readings in history.

I don't really know how he pulled it off, other than that he was away on "business" frequently.

Something Wasn’t Right factsShutterstock

14. That’s Just Wrong

My ex's brother helped his friend (he was friends with the couple, but clearly "chose" the guy) hide assets and wash cash in the six months leading up to a "Surprise, I'm divorcing you"! by the friend to his now-ex and deceased wife. But oh, it gets so much worse. He did this because she had just been diagnosed with cancer, and was not going to live.

He didn't see why "his money" should go to "her health care" when she was going to "die in a few years" anyway.

Nurses Ghost Stories FactsShutterstock

15. Feeling Bad For The Children

I’m an attorney and a foster parent, and my wife won’t sit next to me when we have to go to court for our kids because I usually have a running commentary on how inept the attorneys are. The judge for this type of case knows me and knows I’m an attorney, so he finds this entertaining. The last time we went in, there was one attorney, who is my FAVORITE, in the case before us.

Myself, the judge, and every other attorney hate her because she is oblivious, loud, and incompetent. So she stands up in this case and goes “Your honor, my client has only been found guilty of child endangerment in another county. I see no reason that this court should hold that against him when it comes to the custody of his children”. The judge did not agree.

Lawyers Screwed factsShutterstock

16. Doesn’t This Guy Have Anything Better To Do?

Story from my parents who are lawyers. So throughout the divorce proceedings, there was a car that was a huge point of contention between the husband and wife. After months and months of saying he would never let the wife have the car, the husband concedes in exchange for something great, like one of their summer houses.

It turns out he had been driving the car for three hours every day in a big loop around the city, putting thousands and thousands of miles on it basically making it worthless. The amount of planning and spite that went into that was amazing.

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17. There's Always A "But"

This guy wanted custody over his children after a divorce, but his wife was accusing him of physical harassment. He was asked if he had ever laid his hands on his wife, and he straight-up said: "Yes, but only when she annoyed me". I was ready to leave the courtroom and laugh.

Rest My Case factsShutterstock

18. The Self-Fulfilling Defense

Currently studying law. One of my tutors told me about a case he had while working for the state, where the defendant tried to claim that being an orphan had given him severe PTSD and mental illness and he was unfit to stand trial. Unfortunately, he was on trial for murdering his parents, so it didn't really fly.

Sleepover disastersShutterstock

19. Told You So

I was in court, and the case before ours was going on way longer than it should have. The defense lawyer calls for a motion to dismiss, claiming lack of evidence. The judge says he will entertain said motion after lunch, hits his gavel and says court will reconvene at 1 pm, court dismissed. The defendant stands up and says real loudly, "Told you I could get away with stealing that stuff"! He thought his case had been dismissed.

Lawyers Screwed factsPublic Domain Pictures

20. Better Taxidermy Than Estate Tax, Am I Right?

In my trusts & estates class in law school, we read a case about a man who left everything to his wife, but only if she got his body stuffed and left it on the living room couch forever. Luckily for her, the court invalidated that part of the husband's will. If I recall correctly, part of the reasoning was that it would make it impossible for her to date/remarry if she had her husband's creepy body glaring at anyone who came to see her.

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21. The Beauty Of The Bodycam

I represented a client who was put into custody for being under the influence while driving, and he swore up and down to me that he hadn’t been drinking. The case involved a newbie officer who had his field training officer with him in the car. The rookie pulls my client over for a tag issue and walks back to the car with his body camera still on. The recording went like this:

The training officer says, “Book him”. The rookie says “But he’s not intoxicated” to which the reply was “Do it anyway”. Then the body cam clicks off. Seven minutes later, it turns back on, and they’re doing field sobriety exercises on my client. My client sat in custody for three weeks until I finally got the tape from the prosecutor and presented it to the judge.

The “Uh-oh” looks from the prosecutor when the judge saw the tape...well, I’ll treasure them forever. The judge wrote the chief a letter saying the training officer's career was over, and he’d deny every search warrant the guy tried to bring thereafter.

Said To Police factsShutterstock

22. Maybe They Just Had A Question!

Two guys were being tried for robbing a gas station. A customer who saw the whole thing was now on the witness stand. The prosecutor asked him to describe what he saw. He said that he saw two guys robbing the store and then running out, when one of them bumped into him. Then the prosecutor looked at the two perps and said "Are those two men in the courtroom today"?

At which point, the two idiots raised their hands. Case closed.

Lawyers' defenseUnsplash

23. A Hole In Logic

My firm had been chasing down this woman for years, trying to get her to pay out on a six-figure judgment. She kept nothing in her personal bank accounts and used the money for her business accounts for a rather lavish lifestyle. She kept claiming she was broke and that she didn't use her company funds for her living expenses, including in court affidavits.

During the deposition, she stated she was current on her mortgage for her huge house. We went through all her finances and after a few hours, I brought up the mortgage again and asked, "If you're broke but current on your mortgage, how are you making mortgage payments"? Her face went pale. Utter silence, then in a soft voice: "I use company funds".

Her attorney stopped the deposition and pulled her out of the conference room. My boss started laughing and told me it was a good question.

Lawyers Screwed factsShutterstock

24. Race To The Finish

I'm not a lawyer, but I do have a story related to a divorce case. I once worked on bank equipment, and my favorite was opening safety deposit boxes for the bank. So one day, I was asked to get there before the bank opened, which was really odd. I show up and greet the bank employee—along with a lawyer and a very angry-looking woman.  She is really impatient to get into the safety deposit box. 

I get the lock open and swing the door out, and she's screaming, "Let me in there"! So I stepped outside and let her rush by. A few moments later, I hear a string of loud curse words. It was empty. Then she busts out and storms off, but while she passed she threw down a single piece of paper that had been in the vault. It basically said, "Screw you, witch". It had been a nasty divorce, and the-ex husband got there before she did.

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25. All My Fingers and Toes

There was a guy who cut off all of his fingers. He clearly had some really awful mental illness, I assumed schizophrenia or psychosis, but I never really found out what his deal was. He had decided one evening that a good way to get some money would be to break into a butcher shop and use a meat saw to cut all his fingers and both thumbs off at the knuckles, which is pretty much exactly what he did.

He was found the next morning, somehow having survived. He was put in a mental health facility and made a pretty much full, albeit fingerless, recovery. He wanted to sue someone. He didn't really know who he wanted to sue. He had just got it into his head that if he was injured, he would get compensation. I remember his biggest question was whether he would get more money if he went back and cut off his feet too.

Legal Disasters FactsShutterstock

26. Occupational Hazard Lights

I represented a guy whose car lost its battery in the middle of the freeway at 4 am. He put his hazard lights on and called 9-1-1 for help. At the same time, an LAPD officer in an unmarked car was driving pretty fast. He doesn’t see our guy, strikes him, and causes a major six-car collision, including overturning an 18-wheeler truck.

The authorities arrive and take photos. The LAPD officer claimed our guy did not have his hazard lights on, and he was driving slower than we say. Basically, he was trying to put some of the fault on our guy. At the deposition, the attorney brought photos from the scene...One of the photos showed my guy’s hazard lights on. We were dismissed shortly after.

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27. But You Forgot To Ask About This

At a deposition, it’s the questioning lawyer’s responsibility to ask the right questions, and they have to be thorough and methodical. If they neglect to ask about something, that’s their problem. Those defending the witness always tell the witness not to volunteer information and to just respond to the questions. Again—don’t volunteer.

I had a witness come in, and we went through the whole preparation meeting where I gave her all the instructions and told her not to volunteer. We go through the deposition and she does fine. The questioning lawyer is done, he’s packing up his stuff, the court reporter is packing up her stuff, and the lawyer is walking toward the door. That's when the worst happened.

Suddenly, the witness says “Did you want to see this"? and pulls out a stack of books that no one had ever asked about, she hadn’t told me about, and which contained stuff that the other side was able to use.

Lawyers Screwed factsShutterstock

28. Dear Diary...

I worked a harassment case with a plaintiff who was paid to role play with her boss, and kept a very detailed diary about their, uh, encounters on her work computer. At one point she was asked to read from the diary for the record. She was asked at several points if she wanted her new husband to leave the room while she did this, but she declined. This was, shall we say, an enormous mistake. 

Let's just say it was extremely kinky, she confirmed it was true, and the only mention of her now-husband was that he was boring in bed but she was going to marry him because she couldn't get her first, second, or third choice. He ended up leaving on his own after she read that part out and confirmed that she was writing about him.

Legal Disasters FactsPublic Domain Pictures

29. Gordon Ramsey’s Idiot Sandwich

I had a case a few months ago where a man was charged with shoplifting. It turned out he was 70 years old, had absolutely no record, and had shoplifted a SANDWICH which he ate politely in the store. He honestly thought he had paid for it. I was so angry that he was ever charged in the first place. When I saw him in court, he was absolutely terrified.

I immediately withdrew the charges and wished him well.

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30. Hold Your Temper

I was taking my ex to court over the custody of my kid. I had compiled a 150-page dossier complete with a report from child protective services, since there was harassment in the household. There were text messages and tons of records of this. The ex decided to represent herself because...hubris, I suppose. Or just plain stupidity.

Before the case started, she offered me an agreement that would grant me custody as well as some generous provisions for herself. I politely declined, since we were confident we would be getting a lot more than what she was offering in trial. The case was called up. Our testimonies went in. She put on the most hilariously insane and embarrassing show for the court. In her closing testimony, she attempted to hand the judge the agreement she tried to give us. The judge refused to take it.

“You can't just hand me things. That's not how you submit things into evidence. I'm not reading that”. She's arguing with the judge, yelling at him, and losing her mind. In the insane nonsense she was spewing she said, "and this agreement gives him custody, which is one of the things he's after"! in what I assume was an attempt to show that she's willing to compromise.

My lawyer peppers in a quick statement, "Okay, so you agree for the father to have full custody"? She snaps in heated anger, "Yes! That's what I agreed to"! Our side falls completely silent and the judge, after much effort, ends her little outburst. Gave his final verdict, which started with granting me custody and putting her in court-mandated therapy.

She literally gave away custody of her daughter in a heated argument with the judge.

Lawyers Screwed factsShutterstock

31. That Settles It!

I was at a hearing arguing that my client was wrongfully terminated because the employer failed to abide by the proper procedures. During the hearing, a witness for the employer tried to offer documents that were obviously fraudulently altered in order to make it look like the proper procedure was followed. It was a slam dunk.

I noticed the alteration and was preparing to point it out when the opposing counsel realized what was going on, rushed that witness out of the room, and after a quick adjournment, offered my client a large settlement.

Lawyers Share “I Rest My Case” FactsShutterstock

32. The Test

Picture it: Mother and father are in a custody dispute. The mother's not making a lot of money, but she's hustling as best as she can to take care of her kids. Father's a loafer. He actually was supposed to have primary custody, but skipped out, so she's been taking care of them for a couple of years, and now she wants primary custody officially transferred.

He's fighting it because he's a narcissist. In many jurisdictions, in addition to the lawyer for each side, when there's a child involved, the court appoints a guardian who also represents the child. The guardian interviews the parents, interviews the child, does some basic investigating, and reports to the judge about their assessment.

In this case, the guardian said outright that the mother was probably the better bet, but he thinks that both parents should take a drug test just in case. Well, the judge has no problem with any of that, and sends the parents off to be tested right then. That's done, everybody comes back to the courtroom, where the judge reads the test. The results shocked even me.

The mother tested negative for everything. Father...tested positive for a certain powdery substance. Mom got full custody.

Lawyers Screwed factsShutterstock

33. Lawyers Can Go Mad, Too

I worked at a firm that was subpoenaed as part of a divorce between a partner at the firm and a partner at another major firm. The woman issued more than 70 subpoenas to banks, firms, investment companies—you name it, she subpoenaed it—because she was convinced he had squirreled away $20+ million overseas behind her back.

It got so bad that she dug up receipts from 25 years ago to try to put together this grand conspiracy puzzle. But there was something that she didn't think of. In the end, after she racked up $1.5 million in fees, and seven different lawyers, the judge said this is ridiculous—there was no conspiracy, and you are not entitled to a portion of this phantom $20 million. 

Mind you: this was a major firm partner who was acting this way. She made millions per year in her career. But she apparently lost her mind.

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34. Easy Peasy

My wife is a lawyer. When children reach the age of majority, if they don’t continue studying and start working, it's not necessary to pay alimony. Well, my wife's client found a new lover, which unleashed the wrath of his ex-wife, who started asking for more alimony for her children. To win the case, we needed to prove that the children were working, but we couldn't get any proof.

There wasn't much chance of winning, but we still went to court hoping that with the interrogations they could find information that would put them in evidence. Finally, on the day of the trial, the children did not show up, only the mother and her lawyer were present. The judge says, “Tell me why your children couldn't come".

The mother responds, “They couldn't get permission at work". Everyone went silent. The judge, the lawyers, the mother. Another few seconds of silence goes on before the judge says, “Well, that was fast".

Lawyers Screwed factsShutterstock

35. A Post-Mortem Addition to the Family

I'm a lawyer who works in last wills and testaments. I was working with a nice old lady, when she drops the mic. She confessed that she had a secret daughter, and she wanted to leave the daughter some money and photographs without the rest of her family finding out. Even her husband does not know about the secret baby. That will be a fun conversation when she passes away.

The Weirdest Wills FactsShutterstock

36. The Wedding Photographer

I represented the husband in a divorce. On the day of the trial, opposing counsel presented shocking evidence. The wife’s attorneys produced photographs that they claimed proved adultery. The photos were of my client, the husband, wearing lingerie and a long brown wig, engaging in act of intimacy with another man. I was able to successfully exclude this from evidence...because the wife was the photographer.

Lawyers divorce casePexels

37. But It's My Favorite

This was literally the first thing I ever did as a law student intern. My client has a good defense on a possession case. Substances were found in a jacket, but my guy wasn't wearing a jacket, so they were going to have a very difficult time proving that the jacket belonged to him. I had a long meeting with the client and explained everything. He was excited.

Day of the preliminary hearing, the guy shows up and sits down directly in front of the officer who took him in...while wearing the jacket in question. The exact same jacket we were going to say they couldn't prove belonged to him.

Lawyers Screwed factsShutterstock

38. Learning To Fall

Years ago I worked in personal injury, and we had a woman come to us saying that she slipped and fell outside a nail salon because they hadn't swept up the wet leaves outside the door. So we take the case, and almost immediately we get a call from opposing counsel saying he's going to courier us something important. When we opened it, I almost burst out laughing.

We pop the disc in the computer, and right there is security camera footage of our client picking up the wet leaves, putting them on the sidewalk, and sitting down on them before calling for help. I have never facepalmed so hard. Needless to say, we dropped the case.

Lawyers Screwed factsShutterstock

39. Who Needs Probation Anyway?

The judge was giving a mass ruling for a group of people about their probation for driving under various influences. The judge asks the room, “Has anyone consumed or taken substances in the last 24 hours"? One single dude proudly raises his hand—"I did some dope last night". That single dude did not get probation.

Legal Disasters FactsShutterstock

40. The Devil Is In The Details

I was trying to get a restraining order for a woman in divorce court from her son’s father. She details a story where he grabbed her arm and slammed it on the tub, breaking her wrist. On cross-examination, I asked the accused, her ex, if he ever broke my client's wrist on purpose. Then the true, awful story came out.

His response: “Oh yeah I did"! I'm jubilant....for two seconds. Then he continues. "She was nine months pregnant and about to do crack. I tried to grab her arm to get the pipe and protect my unborn son". She left that detail out in her conversations with me.

Lawyers Screwed factsShutterstock

41. You Had One Job

We had a client who was on the board of directors for a company and was being sued for not telling the board something. I and a few other attorneys spent an entire week prepping this client for his deposition by going over every document in the case and explaining why it was important. On several occasions, we reiterated that no matter what else happened in the case, as long as we can show that he told the board about this thing, he was fine.

The day of the deposition arrives, and disaster ensues. So, opposing counsel sits down and starts questioning our client, and we think we have this in the bag. He just has to say he told the board this one thing. In the first 5-10 minutes of the deposition, the opposing counsel straight-up asks our client what he told the board. Client responds, “I told them about Y, I told them about Z, I told them about A, B, and C”.

He says NOTHING about what he's being sued for, literally the only issue in the case against him. In 20+ years of practice it was the closest I’ve ever come to rage-quitting.

Lawyers Screwed factsShutterstock

42. Going A Little Too Far With The Story

I was sitting in court waiting for my case and there is a basic traffic stop case going on. The prosecutor has the officer walk through the incident. The officer recalls all these details about how he pulled the driver over for running a red light, then noticed a busted tail light. How he stayed cool, calm, and collected, even as the driver became irate.

The officer said the driver was cursing at him and saying he can "Shove the ticket where the sun don't shine". The officer then claimed that the driver ripped up the ticket and threw it at him. He sells the story really well, and I noticed that the courtroom has become invested at this point. The driver is not a lawyer, but chooses to represent himself and takes all of a minute to embarrass the officer and court".

Your honor, the officer testified, under oath, to the court that I acted belligerently, then aggressively tore up and threw away the ticket, which I find hard to believe". He pauses for effect here, and then absolutely slam-dunks. "Seeing as this here is the ticket, in one piece, without even a crease on it". He pulls out the ticket from a folder he had in front of him.

You could hear many in the court gasp, laugh, mumble. The judge stops the driver, looks over to the prosecutor, and without hesitation, the prosecutor replies, "We would like to drop the case". All the other defendants pending their case applaud.

Said To Police factsShutterstock

43. Maybe She Just Forgot

Custody battle. The lawyer for the mom puts her on the stand for the sole purpose of credibility. It all unravels from there. The opposing lawyer starts questioning her about an allegation that she smoked substances with her kids when they were 12 years old. Mom says the children are lying and deflects to the dad's "harassment"...which, by the way, doesn't exist.

During the same cross-examination, the mom admits to “medicinal usage”. When probed, she did not have a card and when asked where she got her medicinal stuff, she said “local dispensary down the street”. Liar, liar pants on fire. Remember...her lawyer put her on the stand in an effort to make HER the more credible parent. It went as badly as it possibly could have.

Lawyers Screwed factsShutterstock

44. Photo Finish

I was involved in a civil suit against an organization that attempted to cover up the battery and molestation of an at-risk population. During a deposition, the opposing counsel began asking an aggressive line of questions accusing the deposed of false reporting in the past, convictions for forgery, and identity theft. After our client answered with a simple “no” to about a dozen of these questions, the opposing counsel became belligerent, and threatened to pull out mug shots at trial.

He pulls out a photo and turns ghost white. It was a photo from his folder, which he put up right close to his face, then shoved it back and suddenly asked to conclude the deposition. Turns out, he had pulled records on the wrong person. I later found out who this other person was, and while their names were the same, the ages were more than 15 years apart.

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45. The Others

I had a family client whose ex wasn’t letting him see his kid. So we were in court with him explaining how important parenting was to him, how much he loved being a father, etc. Well, I was in for a horrible surprise. After 45 minutes of this, the mother says, “I don’t know why he’s saying this, he abandoned his other kids”.

Cue me who has never heard him mention having other kids. It turned out, yeah, he 100% abandoned them, has had no contact for years, and never made any efforts. Please give your lawyers important information, especially if another party involved knows your secrets.

Lawyers Screwed factsShutterstock

46. Not Reading The Room

My law professor was once defending a young woman on drug charges. In court, his strategy was to tell the truth: This woman's life had turned dark due to trauma, but she was now in a steady loving relationship with another woman. For the first time, she had some peace and security, was genuinely working on overcoming her demons, and was unlikely to re-offend again.

It was a 50-50 proposition on how this would land with the judge...until the prosecutor stood up and started lambasting the two women. He claimed they were lying because "lesbian relationships aren't real". According to the professor, "Everyone in the courtroom except the prosecutor knew that the judge was gay", so this did NOT go down well.

The judge tore strips off the prosecutor, gave a furious lecture on gay rights, and ended up giving the woman a tap on the wrist and wishing her well with her partner.

Lawyers Screwed factsShutterstock

47. Chicken Run From Dad

I was representing a mom in a bitter custody fight. The dad wanted full custody and argued the mom was an unfit parent. Mom wanted full custody because the dad had a history of domestic battery toward her and the kids. Dad's lawyer was doing a good job of painting her in a bad light during his cross-examination, and I was starting to get worried.

His lawyer then brought a close family friend as a character witness, who said the usual nice things about dad. Then he said something about them owning chickens. I thought that was odd, so I asked more questions. Suddenly, the cat was out of the bag. I was able to get the friend to spill the beans that the dad owned chickens for fighting, and he'd take his minor children to these fights.

Apparently, when the children were acting up, he would punish them by forcing them to feed the chickens, during which they would get pecked and scratched by these angry, fighting chickens. And obviously, the children were terrified of those chickens. I could see the color draining from dad's lawyer's face. Mom got full custody.

Lawyers Screwed factsPexels

48. All He Had To Say Was Yes

I’m doing landlord-tenant stuff, and my client was facing eviction over non-payment. However, the client was withholding rent payments because of habitability issues in the apartment: No heat, high lead levels, and vermin. I think this is going to be an easy win for me. I told my client continually to make sure that they don’t spend the money, keep it but don’t spend it.

If you show the judge you still have the money, it looks really good for you in terms of making the judge believe that you’re withholding for good reasons. We get up in front of the judge, and the landlord doesn’t even have an attorney. I’m dancing inside, there’s no way I can lose. I was so, so wrong. I make my arguments and the landlord makes his.

The judge asks my client if they still have the money. My client responds, “Nah, I blew all that at the casino last week”.

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49. Absolutely Evil

She took the cats. He wanted the cats. Looked like courts would give him the cats. She had the cats put down.

Why Do Cats Purr EdtriaShutterstock

50. Never Fear, Grandma's Here

This was in a custody dispute, in a jury trial. We represented the father of young twins, and the mother wanted child support. The issue was that, for the past three years, they had been sharing the kids EXACTLY 50-50, as in he got a weekend, she got a weekend, one of them got Monday and Tuesday, the other got Thursday and Friday, and they split Wednesday.

Well, she thought she could get more. The thing was, she did not have a case. She kept taking the kids to CPS and child psychologists before the trial to make a reason why she should have primary custody, but we managed to get all of that excluded. So on the day of the trial, she finally reveals her big argument. These kids have...asthma. The kind of asthma that requires special equipment, and the father is ignoring these issues. He's negligent. He's endangering them. She should have custody.

The trial is generally going our way. She's not a great witness and she doesn't have any medical records to back up these allegations. But the moment that sealed the deal came when the mother called her last witness. The last witness was the children's grandmother, the mother's mother. The jury already knew that she babysat the kids. The mother swore that grandma's apartment was not a dangerous environment for asthmatic children.

But as Grandma took the stand, she leaned over into the microphone and cleared her throat. "Ahecchhhmm". It was a long expression of smoky phlegm. She sounded like decades of three-pack-a-day inhalation when she said it. After a half-hour of deliberations, the jury awarded primary custody to the father. He immediately started crying, while the mother sat motionless. It was a good result.

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51. Hide And Go Seek Gone Wrong

I'm an accountant, not a lawyer. Had a client who was divorcing her husband hide Ziploc bags of ground meat throughout the house (in air vents, the attic, behind water heater etc.) I think it was at least 20-30 bags that took months to find all of them.

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52. Domestic Stupidity

I used to be an advocate for domestic violence survivors, and helped victims get protective orders against their abusers. At one hearing, my client told her story—him hitting her after an argument. The judge asked him, “So, did you hit her"? He says, and I quote, “Now Judge, it was just a little love tap, you know how it is".

The judge blinked twice, stunned, slammed his gavel, and granted her petition.

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53. A Boneheaded Play

I sat in on a personal injury case where the plaintiff broke their leg in an accident and had a doctor on the stand as an expert. The woman's lawyer begins questioning the doctor about his experience with leg injuries (he was a well-known orthopedic surgeon in the area). She asks if he’s ever treated a tibula fracture. He simply answers "no".

So, she starts grilling him with all these questions about the tibula. After about six or seven questions, she asks "how did you get a medical license if you've never treated a tibula fracture"? She launches into a huge rant trying to discredit his credentials, to which he simply responds "there is no bone called the tibula".

The lawyer became beet red and everyone in the room tried their best to keep from laughing, including the judge.

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54. Thank The Lord

I had a client argue that she didn't owe the credit card company because of Jesus. True story. Her basic argument was that debt is a sin (or maybe not paying the debt was a sin? Doesn't matter, she was nuts). And Jesus died for all of our sins. Therefore, Jesus died to pay off her debt. She was crazy, but it was kind of brilliant.

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55. The Facepalm Hall Of Fame

I work as a public servant in a judge's office, and since I have a law degree, I get to be with the judge in some of the hearings. Last month, we had a huge substance trafficking case. I'm talking about 20 or more people involved, months of investigation, undercover agents, videos, audio, the whole ordeal. The hearing lasted three days.

It was time for one of the defendants to take the stand so the prosecutor could read the charges he was accused of. The prosecutor told him that "He was accused of selling, trafficking and carrying x amount of x substances, with the base of his operation being his house, where he lived with his partner". Oh man, his response. He promptly said, "Wait up, I was the one selling, she didn't do anything".

His lawyer facepalmed so hard it's actually recorded in the audio of the hearing. He still pleaded not guilty.

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56. Now This One’s Just Cheesy...

My dad is a lawyer, and he had one person come in that wanted to sue McDonald’s because she got her cheeseburger upside down in the bag at McDonald's instead of right side up....

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57. The Value Of Silence

Lawyer here. During an order of protection hearing, the 6'3" tall muscular tattooed idiot told the judge that my 5'1" tall female client deserved the black eye he gave her because she wouldn't stop running her mouth. He actually expected the judge to be sympathetic or something. The second he admitted to hitting her the judge cut him off and said "Order of Protection granted. Next case".

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58. Some People Are Heartless

Bad separation, wife filed a restraining order on the husband (very common, wasn't a terrible guy but not great either). A year into the divorce his mother was dying, he asked his sister to speak with his ex-wife and ask to bring the kids to see her in the hospital before she passed. The wife never did, instead she went to the court and said he violated the restraining order by trying to contact her (you can't contact someone through another party).

He admitted it and explained the situation, but was found in breach of the order. His mother passed while he was locked up and the wife never brought the kids to see her.

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59. They’re Reaching, Your Honor

Not a lawyer but when my mom was hit by a drunk driver, we were filing a wrongful death suit. And the lawyer for the defense used my mom's cancer to say that she was going to die anyway, so a dispensation was not owed.


60. The Polygamist Without A Brain

I had a client who was trying to get away from a horrible ex and filed a restraining order. The ex shows up to the hearing and makes a big fuss about a truck they bought during their marriage. He said it was his, and she had no rights to it because their marriage was void. This pinged something big in my head. I asked him on cross-examination what he meant by that, and he said that he had already been married in another state when he married my client.

He said that my client had no idea, but that it means their marriage is invalid and the truck was all his. Not only is that not true, but he also didn't even realize the enormous trouble he'd just landed himself in. We promptly turned the transcript of the hearing over to the authorities, who were actively investigating him for bigamy. All for a truck.

Which, by the way, my client kept.

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61. I’m Taking Mew With Me

I worked with a client who wanted language that her cats would be euthanized and buried with her. We had to explain why legally we couldn’t do that. The moral part just went over her head. One of the few clients who ever got under my skin.

Fights That Ended Friendships factsUnsplash

62. What If That Was A Lie?

At my first jury trial, I'm cross-examining the alleged victim, and in answering my question she says, "Oh yeah, I lie all the time"! Needless to say, I won that trial.

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63. No Prompt Needed

I had to cross-examine a custom-home builder who claimed he put more labor and materials into building the home than the contract provided, and he was suing for these excess costs. I was asking him about an email with my client negotiating the price of the construction, and he says that he knew he couldn't build it for that price. That's when my head snaps up.

The supervising partner’s head also snaps up, and opposing counsel goes pale. I go in for the hunt at this point.  Me: You quoted this price? Builder: Yes. Me: You knew you couldn’t build it for that price? Builder: Yes. Me: You knew the homeowner was relying on that quote? Builder: Yes. Me: You knew the homeowner wouldn’t have signed the contract without that representation?

This is textbook fraudulent inducement and he had no idea. I couldn’t believe it. The builder got poured out in the arbitration, and he was slapped with sizeable punitive damages on top of it. Five minutes of testimony sunk his case because he volunteered information without being prompted. Some people truly amaze me.

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64. Sweet Revenge

The wife cheats on her husband during his frequent travels for work. She files for divorce and gets to keep the house. Months elapsed and the husband is still rightfully angry but has no recourse. Then he has an epiphany: "I wonder if she changed the password to the Nest Thermostat"? She did not. For the next year, he continues to mess with the thermostat.

In the middle of summer when they're sleeping in HIS bed, he turns the heat on to 90 degrees at 3 a.m. Middle of winter? Time to shut off the heat and hope the pipes freeze. Away on vacation? Turn the air conditioning down to 55 and let it run 24/7 for a nice surprise bill when they get home.

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65. One Flew Over The Solicitor’s Nest

I work with estates and trust accounts. One time, I had to open a trust account under very strange circumstances. The account was a multi-million-dollar trust for one single beneficiary, the son of the deceased. But there's an eerie detail: the reason the parents were gone? The same son who got the trust had been the one to take their lives...with a hammer. He plead insanity.

He would call once a year from the penitentiary/mental hospital, requesting $50 for commissary (to buy chips and gum). The call was always strange. He was very polite, very doped up. The quality of the call was always very "tinny," like he was far away from the phone.

The Weirdest Wills FactsShutterstock

66. Mistaken Identity

When I was in law school, I clerked for a defense clinic. We had an assault and battery case where there was only one witness to the whole thing, which was the victim. I was sitting at the defense table with the actual attorney, another law student that worked on the case with me, and the defendant. We were all in similar-looking suits as a matter of unplanned coincidence.

The victim was asked to identify the person who committed the assault in court. She pointed to me and not the defendant. Our attorney asked several times if she was really pointing to me and if she was sure, and she said yes. The prosecutor was visibly upset and the trial pretty much ended right then and there, as this was a bench trial and not with a jury.

It was never discussed or admitted to, but I suspect that our attorney purposefully had me there at the trial because of my passing resemblance to the defendant.

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67. Telling On Yourself

My parents have a jewelry store, and the landlord was trying to squeeze them into signing a lease for nearly double what the appraiser said it was worth. Problem was that the lease they signed said when they renewed the lease, both parties were to get their own appraiser, then meet in the middle of the two prices. Well, the landlord didn't like what his appraiser said, so he refused to tell my parents what the real amount was.

For two years, he sent every lawyer in town to try to kick my parents out. They tried everything but legally had no leg to stand on. Well, unfortunately during this time, the landlord developed Parkinson's, and his mind started to go. We finally got him to do a deposition. That's where everything went to the trash for him. It was like he drank a truth serum. He just told all.

My parents' lawyer would ask things like: "Why did you not show the appraisal to my clients"? And he'd say: "It wasn't what I wanted. I wanted them to pay more so I hired other appraisers, and paid them off to raise the price nearly double". By the end, his lawyer just had his head in his hands. We had a new lease within a month for less than we originally even offered, and he had to pay back 75% of our fees.

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68. Lying For The Cheating

When I worked for insurance defense, I handled a case where a man reported his Rolex as stolen. He was adamant that he was at a hotel when it was taken. However, he had no proof he was ever at a hotel during this time. We went through the whole process and finally reached depositions. He gets sworn in, and eventually lets out where he really was.

He wasn't at a hotel, he was with his mistress, and he had accidentally left it at her house. His wife noticed he didn't have it on, so he immediately claims it must've been stolen, etc. Yep, this man decided to hire an attorney and go through this whole circus just so his wife wouldn't find out about his affair. Needless to say, we denied the claim.

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69. By Alien Design

My father is a patent attorney, and when I was around 14, he told me about a guy who wanted to patent the iPhone 3 because "aliens" had given him the design for it.

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70. Radical Honesty

My friend's mom was a defense lawyer for a hospital. Her job was to represent doctors accused of malpractice or anything relating to doctor/patient interaction. She had one case where a female patient had accused a male doctor of groping her several times during a procedure. It was seriously disturbing. Allegedly, the doctor had been coached to say that it's possible that he inadvertently brushed the patient's chest, and that if it happened, it was an unintentional consequence of following standard procedures.

So, they get to the deposition and I guess the first question the doctor gets is something along the lines of, "walk me through what happened". The doctor says, "I don't know what you want me to say, man. I'm a tit guy. Always have been". They settled.

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71. There Is No Precedent for This Level of Ridiculous

I used to work for the Attorney General in my home jurisdiction. A guy who'd had his children taken away for some really horrible stuff (he was crazy and had really insane religious beliefs) tried to get his kids back by claiming they were his intellectual property. He sent notices that he'd copyrighted the kids, and demands for their return.

Then he got the idea that his name and all his kids' names were trademarks, so every time he received a court document that referenced any of their names, he sent us an invoice for trillions of dollars for each use of his "trademarks". It was...the most insane case I have ever worked on.

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72. The Sun Is Always Setting Somewhere

Not a lawyer, but I was in traffic court and a cab driver had got a ticket for running a red. He argued that it was really difficult to see because the sun was rising (morning) right where the light was. He was traveling west.

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73. Worst Case Scenario

We had a couple that were both lieutenant colonels in the Air Force. They had one daughter that was 11. Both had graduate degrees and were generally intelligent people. Well, the husband had an affair and things went sour with the relationship. The daughter was at that age when her relationship with the mother was starting to get a little strained and she mentioned how she wanted to stick with her dad when her parents split.

The mother absolutely freaked. The first thing she did was go to the local PD and claim the father had been hurting the daughter. They investigated and couldn't find any evidence so they dropped the case. The mother, still furious, then goes to the Air Force Office of Special Investigations and reports the same thing.

The Air Force then suspends the husband from duty and conducts their own investigation, same result (no evidence of wrongdoing) and the case is dropped. The mother then goes to the next state over where the husband is about to be transferred and contacts the local PD there with the same story. They do their own investigation but get the same result, the case is dropped.

Of course this whole time the daughter has been interviewed a dozen times by psychologists, various therapists, the authorities, the Air Force, and who knows else. The daughter is straight up traumatized by this. Not to mention the harm it did to her father's career. He was basically screwed from any possible promotion just because of the allegations.

Well, once word of all this gets back to the judge, he is furious. He's a former Air Force Jag and still has contacts in the ranks, so he can actually do some damage. The couple comes in front of him one day for a hearing and he outright tells her the ex-wife that she better stop this behavior or he's going to hold her in contempt of court for the maximum amount of time he can lawfully hold her in a cell.

He also said he'll contact the DA and recommend the filing of charges, contact her Air Force superiors and recommend reprimand to the fullest extent possible, and basically anything and everything he can do within his power. It was one of the most messed up things I've seen during my relatively short experience in the courtroom.


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74. Not Your Average Loophole

My uncle represented this guy getting a divorce from his wife of 15 years. Super terrible breakup and they split everything 50/50, even the land that the house they lived in sat upon. Well, she decides to build a house right behind the other house, mind you this was a lot of land, probably 200 yards separating both home sites, so that the back of the houses faced each other.

The house gets built and my uncle gets a call from his client asking about the legality of a situation he had gotten himself into. Apparently, his ex-wife would spend a lot of time in her backyard, so he saw her all the time. What he did was buy a female dog and name it the same name as his ex-wife. I think you can guess where this is going. 

Anytime he would let his dog back in from letting her out he would yell "Susan you [female dog]! Get in here"! He would also yell if she was peeing on the flowers,"Susan! Quit peeing on the flowers"! or "Susan! Quit digging in the dirt"! The ex-wife called the authorities on him a couple of times, but there was nothing they could do because the dog was registered under the name of Susan, and it was in fact a female dog, so there you go.


Elizabeth Holmes FactsWikimedia Commons

75. The Virtue of Honesty

I was involved in a pretty messy custody case. The other party was a mess and had kept the child from my client for weeks. He was playing lots of stupid games and kept requesting continuances. I requested a drug test, which the judge ordered. However, the guy showed up, stood in front of the toilet for literally 2 hours, and claimed he couldn’t pee.

I was representing the plaintiff, so the burden was on me. I called multiple witnesses who testified to the defendant’s substance use. So, opposing counsel decides to call their client for direct examination and asks, “You don’t use crack or coke right"? I fully expected the defendant to just lie and say he was clean. After the question, there was a really long pause and then the guy said, “Yes, I do both of those".

My head almost exploded. I didn’t ask any questions on cross-examination because I didn’t want to muddy the waters. I won, and the child is doing great.

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76. Munificent Motivator

Oh boy, I'll never forget this guy. Client: "I'd like to leave $100,000 to my son, $100,000 to my daughter, and $10,000 to each of my ten nephews". Lawyer: "But sir, your estate is worth about $500. Where are your heirs supposed to get this money from"? Slamming his cane on floor, the client roared, "EARN IT, JUST LIKE I HAD TO"! He did not like hearing that this isn't how wills work.

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77. A New Meaning To Plea Bargain

Several years ago, I was doing a civil trial (personal injury), defending a woman who allegedly hit a bus monitor with her car. We had offered to concede liability and just try damages—in other words, the jury wouldn't hear the circumstances of how the injury happened, just that we agreed my client caused the injury, and they would only decide the amount of damages.

We had evidence that the plaintiff was significantly exaggerating her injuries. The plaintiff's attorney refused to agree to our concession, thinking that if the jury heard the circumstances they'd want to give even more money to punish my client. So, we went to trial on liability. The plaintiff called one witness, her client, who testified that an older woman in a green car hit her.

They rested and I moved for a dismissal for failure to prove a case. There was literally no evidence connecting my client to this incident, just an older woman in a green car. The plaintiff never bothered to call my client to the stand. The attorney told the judge that the bus driver had written down my client's license plate and gave it to the authorities. They never bothered trying to find the bus driver.

The attorney asked if she could just put the report in and I objected that it was hearsay. The attorney then actually said, "Please just let me put this in, I haven't had work in a while and I got retained by a firm to try this case, I really need to win this".  Of course, I didn't agree, and the judge dismissed the case. I felt a little bad for her but that was maybe the worse presentation of a case I ever saw.

I spoke with the jury afterward and they all said they hated the plaintiff, didn't believe a word she said, and likely would have found in my favor anyway. Moral of the story, BE PREPARED IN COURT.

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78. To Beyond The Grave

I advised on a will where the deceased had left considerable assets to people who had already kicked the bucket by the time the will was read. There is nothing unusual in that per se, except that these individuals had passed on long before the will was made. The lawyer apparently asked the guy, "You know you're giving your money to dead people"? and even sent him to a doctor to make sure his mental state was okay.

The doctor gave him a full bill of health and said he was perfectly compos mentis, so the will stood.

Crazy Wills FactsShutterstock

79. Don’t Be Rude

I was in court for a hearing. The judge was already in a bad mood and asked why we were here for such seemingly pointless litigation—without giving details, he was right. The barrister starts to make our case, and I'm taking notes about areas we need to further explore when I hear, "EXCUSE ME, WHY WERE YOU SO RUUUUUUDE TO ME"?

The client, who had been told to NOT COME, had come to court that day and was evidently incensed by the judge questioning the merit of their case. They berated the judge for about three minutes, with me and my co-counsel first stunned and then trying to shut them up, before he adjourned the hearing. It was an amazing sight to see.

The case did not go very well, to my client's surprise and fury.

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80. Pro Bono Mishaps

Someone I knew had a pro bono case where she had to defend a person who had been charged with an offense—I don’t know what, it is confidential, but I do know it was circumstantial at best. So she instructed him to shut up and let her do the talking during the trial. She pleads and can show that the court has nothing on her client, and she feels that for once, a pro bono case is going her way.

After her plea, the judge thanks her for her plea and turns to her client. He asks if the client had something to add to the plea. Client looks at her, back at the judge, tears well up in his eyes, and he blurts out: "I'm so sorry, I'll never do it again"! She threw her notes and everything else she had in her hands at the client. She basically got screwed by her own client, who screwed himself even worse.

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81. Kiss And Tell

I worked as a paralegal when I was in college. We had this massive case with a lot of people involved that had spun out into a bunch of little side cases. In one of those side cases, this guy was claiming our client had left him threatening voicemails so he and his wife sued for loss of consortium. When I found out what that meant, I was stunned.

Loss of consortium, and I swear to you this is a real thing, basically means something happened that is stopping a married couple from doing the deed, and they want to sue you over it. The guy was claiming that he was so scared by these voicemails that he couldn't sleep with his wife anymore. Deposition time rolls around, and I'm sitting in the other room, but it's a small office and I can hear everything.

My boss starts asking the wife how we're supposed to know that it was our client's fault they stopped doing the deed. Maybe she's just not as attracted to him anymore. Maybe he's not attracted to her. Maybe they didn't have that much of a bedroom life to begin with, etc. Her reaction was unhinged. This woman starts yelling "I love sex"! and banging her fists on the table.

Her lawyers try to calm her down and tell her to stop talking, but she keeps on shouting "I love it! We used to have do it two, three times a day! We'd be thrown out of hotels because of the noise we'd make"! And to the protestation of everyone in the room, her counsel and ours, she proceeded to describe their intimate history in graphic detail, all of which was recorded in the deposition and filed with the court.

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82. Judges Don’t Really Like The Thug Life

A young woman and a young man have a child. The young woman seeks divorce from the young man because he enjoys the "thug life". He had recently been taken into custody and charged with possession. The young man doesn't like her leaving him. He hires a local big-name divorce attorney and gets a temporary divorce order entered saying she can’t have overnight guests of the opposite gender.

The young woman starts seeing someone new. The young man is very upset about this. He has his fancy lawyer ask for a hearing accusing her of violating the court order. He's also seeking full custody of the kids, on top of attorney fees. It's starting to turn into a mess, so the young woman, on advice from a mutual friend, hires me for this hearing.

I sit down with opposing counsel, and she basically tries to strong-arm me. Her demands are beyond. She says the mother must not only give up primary custody, but must have visitation with a supervisor and pay child support and attorney fees. She knows I'm a new baby attorney in town. She says that she'll see us in court.

I go into the hearing with a copy of the guy's probation arrangement from his earlier charges. See, he's an idiot and hasn't told his attorney about this, and she is blissfully unaware that he has a record. She calls him up and establishes how my client had her new boyfriend over on these different nights. The judge is VERY conservative and not pleased.

But then my line of questioning changes everything. I ask the ex-husband if he has a job. “No". What do you do for money? “Things here and there". Oh? Your lawyer is awfully expensive. Do you sell substances"? "What"? "Have you ever sold substances to make ends meet"? "Uhhh no". I then introduce a copy of his guilty plea and straight probation sentencing.

Judge is now staring daggers at him. I lean over to my client sitting next to me, and whisper, "If you took a drug test today, be honest, would you be completely clean"? She says "Yes". I ask the young man, "When was the last time you used"? His attorney objects, but the judge overrules. Now I know I've got him because I know this judge will test people on the spot and has done it many times before.

The disgruntled ex says, "It's been years, I'm clean". "So, if you were tested, you'd be clean"? "Yes". Opposing counsel asks the same of my client, and we agree. The judge has them both tested. He tests positive. My client is clean. The judge denies his motion, and asks me to send in new temporary orders where the young man is required to maintain employment and start paying child support.

But then came the best part. The icing on the cake is that the opposing counsel actually called me and left me a voicemail congratulating me on, and I quote, "Handing her butt to her for the first time in a long time".

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83. Status Update: You Lose

I was representing a plaintiff in a hit-and-run case. Despite me preparing her for several hours the previous day, this client was an absolutely terrible witness for her own case. Just the worst. She couldn’t even identify the street she was crossing when she was hit by the car. The “gotcha” moment came during cross-examination.

The defense counsel pulls out a picture of my client dressed up and ready to hit the club, which was posted to Facebook the day after the alleged accident. I, thinking quickly, object because the timestamp refers to when it was posted, not when it was taken. So the defense counsel shows the picture to my client and asks her when the picture was taken.

She confirms that it was taken the day after the accident—i.e. when she was supposedly in unbearable pain.

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84. Restraining Order Backfire

A wife filed for a restraining order because she wanted the house during her divorce. The husband has a good job, like $200k per year. The employer finds out about the restraining order and fires the husband. He was a very specialized employee, so the only job he can find close to the house and his daughter is $50k. Ooh boy, did this not go well.

The house gets foreclosed. Child support is set at less than $500 per month. The wife has to get a job as a waitress.

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85. A Shocking Turn of Events

The strangest, and most embarrassing, will reading was in a room crowded with relatives when a man who passed fairly young left absolutely everything to his 26-year-old stepdaughter, which was quite a lot of money and property. The two ex-wives and his children from the first marriage got nothing, nor did siblings, nieces, nephews, etc. The will specified that a DVD be played to explain why the stepdaughter was getting everything.

Like everyone else, I thought it'd be the guy explaining the big "screw you" to the rest of the family. What followed was completely unexpected. It was a hidden camera recording of the guy and his stepdaughter going wild in bed together. The video started in mid-action, with her screaming "Yes oh god yes"! It had obviously been edited to start with maximum shock value, and it worked.

It took about 30 seconds for me to recover enough to turn the thing off. It was definitely the biggest "holy moly" moment of my career. I later learned that the guy and his stepdaughter had a relationship since she was a teen, all the way to when he passed (when she was 26). Apparently, though this is second-hand and I can't confirm, there were multiple clips of various video bits through the ages on the DVD.

At the end of the DVD, the guy explains that the stepdaughter gets everything because she'd been "the best lay of his life". The worst part was that the will specified that I was to give every single family member their own copy of the DVD. The copies had been kept in a box and had been distributed prior to the showing, so everyone had "The Best Moments Of" in their hands, at the time the DVD was playing.

Epilogue: the family sued and lost, believe it or not. The girl got to keep everything.

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86. Too Big to Know Better

As a corporate lawyer, the most ridiculous argument I come across almost monthly is as follows: Fortune 500 company signs a garbage contract and is going to lose a lot of money due to the plain language of that contract; Fortune 500 company argues unconscionability—specifically that said company was not sophisticated enough to read the contract and no reasonable person would ever agree to the term or terms in dispute.

In sum, multi-billion-dollar firms claiming they're incapable of reading contracts.

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87. Self-Sabotage

This will always be my favorite. I was doing a boundary dispute, a squabble over what was essentially a few inches of land. The other side was a lawyer, and an absolute jerk. He was acting for himself—even though he was a deeply unpleasant guy, he thought he was the smartest guy in the room. Part of his case hinged on wheelie bins and how before the boundary was moved, there wasn't space to store a full-size bin beside the house.

The fact that you now could means that clearly the boundary must have moved. That was the extent of his evidence. It really was thin stuff. But man, he had an idea and he was sticking to it. During the actual trial, he pulled a fast one by suddenly producing an old aerial photo, ostensibly to show the boundary at the front of the property had also moved.

Generally, you have to disclose stuff like that in advance. You can't just sit on something relevant and then suddenly whip it out at trial with a flourish. But it backfired horribly.  While he made his submissions, I looked more closely at it. I then realized that it very clearly showed a wheelie bin in exactly the spot his case said there couldn't be one.

I told the judge we were happy for the photo to be admitted after all, got the other side to confirm the date it was taken, then pointed out he'd just completely screwed his case. Couldn't have happened to a more deserving chap.

Lawyers Screwed factsShutterstock

88. Her Own Worst Neighbor

I have a brief encounter (personal injury prospect): An old lady slipped and fell on an icy driveway that was not salted or maintained, so she wanted to sue for damages. After hearing the story, turns out the lady fell on her own driveway which she did not salt/maintain. She was wanting to sue herself.

Crazy neighborsUnsplash

89. Good Call

This never made it to court. I asked my divorce lawyer what was the worst thing a client had asked him to argue. I was expecting a "I want the salad spinner"! sort of story. He had a client, a professor in his 70s who was divorcing his wife, also a professor in her 70s. They were both Jewish. His wife had a tattoo on her arm. It was a number, put there by the Nazis when they put her in a concentration camp in WWII as a child.

The husband was born in the US, and was not German. The German government was in the process of settling a case with the survivors. She had some amount of money, a six-figure sum, due to her. The husband wanted his lawyer to argue that he should get half the settlement money. The lawyer told him that there was a special circle in the afterlife for lawyers who ask for stuff like that and that he was not planning on ending up there.

Unforgettably Brutal Last MomentsShutterstock

90. Psycho: The True Story

In October 2020, my husband and I were renting in a duplex where my father-in-law owned the half we lived in, and a separate family (an adult daughter acting as a caregiver to an elderly mother) owned the other half. We brought our son home from the NICU in August, and towards the end of September, the caretaker neighbor started to pound on the shared wall if she could hear him cry.

The pounding escalated over the next two months. And then it took a cruel twist. The younger caretaker neighbor bought a megaphone to yell through the wall and threatened to “rip us apart". She called us child predators, and she’d yell threats until 3 or 4 in the morning. The authorities were called multiple times, but nothing could be done about it.

One officer told us “The threats don’t mean anything if you don’t actually do it". The elderly mother hadn’t been seen in several months, but requests for wellness checks were brushed off. The general advice I got was that as renters, we couldn’t do anything. It was also suggested that this was reasonable behavior, since the crying baby was probably really annoying.

Eventually, we moved in with my grandmother for our safety. This was after the neighbor busted a softball-sized hole through the shared wall to scream at us, and occasionally just stare at us. But the outcome to this was almost indescribably wild. See, the smell that came out of the hole was awful. We should have known something was up then.

Our security cameras also recorded her coming to my son’s nursery window at around 2 am almost daily, just staring and holding her cat. It took until the end of January for the authorities to be able to enter her property. When they arrived, they discovered that the elderly mother had been deceased since at least June, and the daughter had the corpse dressed in her Sunday best, rotting in a deadbolted bedroom.

The news article said the mother passed from natural causes. The daughter was taken to an inpatient psychiatric facility.

Not What It Looks Like FactsShutterstock

91. Doing His Duty

This girl spent almost the entire case berating the guy she claimed was the father of her baby, having people analyze genetic similarities between the child and the “father,” and going on about how this was all ridiculous because she hadn’t been with anybody else in years. The judge finally looked over at the guy and asked him if he had anything to say in his defense since he had just been standing there quietly while taking this verbal assault from his ex-girlfriend.

He motioned to show that he had a folder of paperwork. The bailiff took it up to the judge, who looked it over and then immediately dismissed the case in the guy’s favor. It is then explained that he had been actively deployed by the Armed Forces for the past four years, and wasn’t even in the country at the time that the baby was conceived.

Near-Death Experiences FactsShutterstock

92. Jesus Walks

I had a potential client come in and say that he wanted to sue his uncle for murder. Setting aside the fact that you can't sue someone for "murder," I asked him: "Who did your uncle murder"? He replied "Me". I turned the case down.

Lawyers ridiculous casesUnsplash

93. Animal Instinct

A woman called saying that she had a product liability suit involving animal crackers she gave to her daughter. I was thinking it was going to be something to do with food poisoning and kept listening. I wish I’d never heard her next words. She explained that when she looked at the crackers, it looked like the monkey was holding its nether regions.

Well, nope, it was a banana. Still, this woman was mortified and ashamed. She said she told all her co-workers, and they were very shocked and uncomfortable. I wanted to tell her she was nuts and that they were probably freaked out, but I didn’t.

Lawyer Plot Twists ExperienceShutterstock

94. Latte And Order

My family friend is a lawyer. She had someone come to her asking to sue Starbucks because someone spilled their latte on the sidewalk and she slipped on it and hit her head. She claimed Starbucks was at fault because it wouldn't have happened if "Starbucks didn't put extra slippery whipped cream in the drink". My friend did not take the case.

Lawyers ridiculous caesPexels

95. A Good Foundation

So, I do a lot of insurance work, and I try cases of all kinds, large and small. I had a small case, over about $2,600, from where a contractor drove into a retaining wall at this lady's house and damaged it. He wouldn't fix it, and, after like eight months, the homeowner allowed her insurance company—my client—to have it fixed and then sent the bill to the contractor.

Surprise surprise, the contractor wouldn't pay. There was lots of squabbling between my client and the contractor's insurance company, who offered less than $500 on a $2,600 bill. We had a trial to settle it. I brought our claims adjuster and the homeowner. The defense attorney brought the contractor and an adjuster from the contractor's insurance company.

Everything goes fine with questioning the homeowner, who was a sweet, middle-aged woman. She, like most people, knows nothing about the finer points of masonry. Then, we get to my claims adjuster. He says, "Well, we paid $2,600 to have this fixed, but I'm not an expert on masonry". However, he also discussed how estimates on masonry were made.

I close my proof. Next, the contractor gets up on the stand. They go over what exactly happened with the retaining wall. Then, he testifies that he "knows for a fact" that the $2,600 invoice includes overhead and profit and accuses my client of "running a scam". The judge strikes the answer. I look down at the estimate for repair and grin from ear to ear.

It says, in bold print, "This amount does not include overhead or profit". I look at the invoice. It's the same amount as the estimate. This guy is lying through his teeth—and I’m going to catch him.  On cross examination, I show the contractor the invoice. "Sir, this is a $2,600 invoice for repair, correct". "Yes". Then I show him the estimate".

Sir, this is a $2,600 estimate for the same repairs, correct"? "Yes". "They're the same amount, correct"? "Yes". "Does the estimate say it does not include profit or overhead"? "Uh". "Does it"? "Yes". "Didn't you just testify that you knew for a fact that the estimate included overhead"? "I don't know". "What don't you know"?

At this point, the contractor is furious and beats his hand on the stand. "It doesn't include overhead and profit, does it"? "I guess not". "But you said it did, right"? I pass the witness. But I wasn’t done yet. Next, the defense attorney calls the contractor's insurance company's adjuster. He testifies about how much he thought it should cost, like $500.00.

I cross-examine him. "How did you make this estimate"? "I put the numbers into a computer program". "How do you know what numbers to put in"? "Uh". "Are you a contractor"? "No". "Are you an expert in masonry"? "No". "Have you ever worked in construction"? "No". "And the computer programs spits out what you put in"? "Yes".

"And you can just put in whatever numbers you want"? "Yes". "And it makes an estimate based on the numbers you pick"? "Yes". "But you don't know anything about masonry"? "No". The adjuster just testified that he made up the estimate. Defense closes proof. And the judge takes the matter under advisement. So let’s recap all this glory.

The contractor lied and was discredited, and the adjuster for the contractor admitted he just made everything up. We got $1,000 out of the trial. Less than half of what we sought but double what the defendant argued it should be. It was a win in my book.

Lawyers of redditUnsplash

96. Not A Lucky Divorce

This woman won $1.3million in a lottery pool and filed for divorce 11 days later. She never mentioned her lottery winnings to her husband. She also did not disclose the proceeds during the divorce. She would have gotten away with it too, if it hadn't been for a letter that arrived at their former marital residence over two years after the divorce…

The letter was an offer to buy out her lottery annuity with a lump sum payment. The husband promptly lawyered up and the family court awarded 100% of the prize proceeds to him.

Lawyers divorce caseUnsplash

97. I Don’t Think That Word Means What You Think It Means

This was unbelievable. My co-worker’s girlfriend filed for divorce a few weeks ago. That's right, girlfriend. They aren't married, and common-law doesn't apply in my state. They lived together for five years. She has a job. She isn't on the mortgage. And she left him a few months ago. There are no kids involved. They were never engaged.

In the "divorce," she wants him to leave his house and she wants to be the one to move back in. She also wants him to pay her $2,800 a month for some reason. I referred him to my divorce attorney, and now that attorney is probably going to represent him. The chick is nuts. She has already tried to get a restraining order against him that was dismissed.

Lawyers ridiculous casesPexels

98. Consider The Source

My dad is a physician and is sometimes called as a professional witness for malpractice cases. In one memorable case, a family was suing a doctor for something fairly frivolous, and my dad was a witness for the defense. The lawyer representing the family was cross-examining my dad, and brought up a chapter in a medical textbook and asked my dad to read a highlighted paragraph.

He does, and the lawyer says something to the effect of, "So, what you just read means 'blah blah medical thing'". My dad confidently replied, "No, it does not mean that". The lawyer says, "No but if you read xyz, the author clearly states 'blah blah medical thing'". Again, my dad says, "No, really, that's not what the author means".

The lawyer didn’t know what he was getting himself into. "How do you know that's not what the author meant"? Dad replies, "Well, because I wrote it". The judge basically facepalmed while the lawyer mimicked a goldfish and stared at the author's name on the chapter. Basically the best moment of my dad's professional life. And yes, the ruling was in the defendant's favor.

Lawyers Screwed factsShutterstock

99. Miracle Babies

My ex-wife is suing me for child support…but I don't even have the “equipment”. I lost it when I was 14 due to a major health problem. I married a woman who at the time claimed to be asexual, however eventually she told me that she was pregnant with twins with a man she was sleeping with. We divorced before the children were born. This is now four years later.

So I received a letter in the mail that said I'm being sued for child support. The children are definitely not mine and we divorced before they were even born. I'm in a horrible situation, my health is very poor and my finances are very, very limited. I'm barely affording to survive here.


Frivolous Lawsuits FactsShutterstock

100. Get OUT

I think my boyfriend has been secretly drugging me for a while now and is gaslighting me. I know this is going to be hard to explain, but I have been having gaps in memory that I have been explaining away as being tired, or overworked, or whatever else. I was going to ask my boyfriend about it, since he is a doctor, but then I started to notice one chilling thing.

This seems to happen when I go on dates with him. I know it must be crazy, but I have woken up with dried…stuff…on my chest several times with no memory of the night before. I know it’s him, too. The first time it happened was when we were drinking and I wrote it off as too much to drink. But then there were a few times when I KNOW we were not drinking.

I decided to break up with him over it…only to suddenly find myself on a date with him a few days later. I had not yet had the conversation to break up with him, but planned on it next time I talked with him. I remember being at the restaurant, but nothing before that. My car and his car was in the parking lot too so I was confused. I decided to play along when he asked me to come back to his place.

After three days at his place I remembered everything so I was starting to trust him again. I was going to ask him about my memory issues when he randomly pointed to these red bumps on my thigh and said I should be treating those sores. I had completely forgotten they were there. These little red bumps that look like needle injections that got infected. I got so freaked out he mentioned them that I decided to leave.

The next day he came over to “Check on me” and I remember waking up in bed with no memories. Then today he met me for lunch saying we had agreed to meet. I never agreed to meet with him and would never want to now. He does this all the time, saying we agreed to do something I have no memory of. I am sick and tired of it and want him punished.

This has started to affect my work life as well as I start to get paranoid when I see a boss walk into a room after making eye contact with me. I get paranoid that they are about to fire me. My friends also state I have been acting strangely and out of character. I have even begun to lose sleep and sleepwalk when I do. Is there a way to have blood work done to see what kind of drug he is using on me?

Tipping Point in Relationship factsShutterstock

101. When It Hits The Fan

I worked at my local district attorney's office as a prosecutor when I was a freshly minted lawyer. We had a special setting trial on a case that had been reset too many times. The week before, it became clear that this particular case was going to finally be tried. I was ready at the State's table waiting for defense counsel when he walks in and tells me he was going to ask for a continuance.

I'm pretty sure I laughed, thinking that it was never going to happen. I was so, so wrong. So the judge walks in angry that he has to sit through another continuance request. Meanwhile, I get the aroma of something foul in the courtroom and I can't place where it’s coming from. The judge asks the defense attorney why he needs another continuance and the defense attorney pulls out his briefcase and opens it.

I'll never forget what he pulls out. It's a Ziploc bag with soiled underwear inside. It turns out he had an accident in his pants that morning in court. He was an elderly attorney and was taking stool softeners. The continuance was granted, and in fact, the entire courtroom shut down for the day to allow maintenance time to clean and shampoo the seats he was sitting on.

I have no idea what ended up happening in that case, I never tried it, maybe another prosecutor did, but this was one of my more memorable "I rest my case" stories that I've seen a lawyer pull off.

Rest My Case factsShutterstock

102. A Fatal Mistake

I once had a client who was a nurse that had administered a fatal injection and ended the life of a baby. It was a long story, but I got her off any charges of negligence despite being very disturbed by what had happened. It happened many years ago, but this case will stay with me forever. Here is the full story, for all of you who might be interested.

It was after hours in a small rural hospital. They were understaffed and under-equipped. In the pediatric ward, a baby was very ill with gastroenteritis and hadn't responded to weeks of treatment. The baby was losing weight despite everything. There was no doctor on the pediatric ward that night, or, in fact, in the entire hospital.

When the lab phoned the baby's blood work results in to the nurse on duty, she said that the baby was going to pass soon if he didn't receive urgent treatment. The nurse phoned the doctor on the telephone. He wasn't supposed to go in that day, having already worked long hours that day. He was just supposed to be available for phone calls.

The doc gave instructions for a sister to give the baby an ampoule of potassium chloride. She wrote down the instructions. But the doctor made a fatal mistake. They didn't specify that it should be given orally, which was what was meant. But because the doc specified that a sister must give it, the nurse assumed that it should be an injection, as she herself wasn't qualified to give injections but a nursing sister would have been.

The nurse called the sister from the maternity ward and asked her to come by and carry out the instruction. She explained the urgency. The sister was very busy in the maternity ward, but came to the pediatric ward and gave the injection. The baby passed from immediate cardiac arrest. The partners in my firm didn't want to touch the case, as they thought it was impossible to win.

But in our law, negligence has a specific definition. I won the case for the nursing sister by arguing that my client was trying her best, with only the instructions and resources at hand, under circumstances where she had been told the patient would pass very soon if the treatment wasn't given. She was an amazingly dedicated person and what happened had completely devastated her.

It was to the point where she wanted to quit nursing. I hope she changed her mind after that. There is one other point, though. The one good thing that came out of this tragic event was that I mentioned to a local Rotary Club member that the hospital in question desperately needed some telemedicine equipment, knowing that the club had such a project.

Shortly after that, they were able to make a donation of equipment to the hospital. I even coincidentally saw that doctor in passing years afterward and the doctor was so grateful for that equipment. It definitely changed the situation and made it far less likely that a tragedy like this one would ever again be repeated at that hospital.

Lawyers wish could forgerPexels

103. X-Ray Vision

There was a case where a client had radiation burns from an X-ray machine. In the avalanche of documents received from the defendant during discovery, there was an internal memo. This one piece of paper cracked the whole case. The memo described a serious problem with the machines and continued, "This is an issue we can't ignore. Unfortunately, it's not in the budget.”

When the case went to trial, we told the jury, "Show them they need to put this in the budget next time." The jury complied, handing down one of the largest verdicts California had ever seen.

Lawyers Screwed factsShutterstock

Sources: Reddit, , , , 5, 6, 7, 8, 9, 10, 11, 12,

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