Sadly, a regular day in court is a lot less dramatic than an episode of Law & Order. Paperwork and mundane interviews fill the billable hours way more often than jaw-dropping testimony and shocking revelations. That’s why lawyers themselves delight in those rare “I Gotcha!” moments, when the client or opposition commits a fatal flaw, and the (legal) evisceration can begin.
Reddit asked lawyers to share the moments in their career where someone screwed up so badly that it should’ve been illegal (and sometimes really was…). Raise an objection to these shocking legal stories of lawyerly “Gotcha!” moments.
1. Lady Luck Failed to Testify That Day
A woman backed out her car directly into a truck in a casino parking lot but luckily it was just a little fender bender damage. My client, the truck driver, 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. I asked if she was a frequent visitor of casino, and if she had a rewards card. She was happy to tell me that not only did she have a rewards card, she had gold status.
I subpoenaed her rewards cards records. She played slots for hours after the accident.
2. Ensured to be Screwed Over
My client’s house burned down from an explosion in the fuel oil tank. It was clearly the oil maintenance company’s fault, but his homeowner’s insurance still refused to pay out, citing a ridiculous technicality. Essentially, the policy covered damage caused by the oil heater, but they claimed that because the storage tank exploded, they didn’t need to pay.
During a deposition with the claims adjuster, I asked how she came to the conclusion that the storage tank was not a part, or at least connected to, the heater. She states that she relied on her “expert witness” who was an engineer. Little did she know, I checked this person’s background. He had zero engineering experience.
As you might know, you don’t get attorney’s fees in most cases. However, you do when an insurance company denies your claim in “bad faith.” Her little admission cost the company about 500k in fees, on top of the original claim for 1.2 million. Kaboom, lady.
3. What’s a Stabbing Between Friends?
I heard a defendant say, “I mean I did stab her… But it was a gentle stabbing…” Dude’s lawyer nearly cried.
4. We Have Lawyer-Client Privilege For a Reason
A former client filed for bankruptcy and brought an action against his landlord too. To prove “damages,” he needed to show that he paid my firm for legal fees connected to the dispute with his landlord. So, this former client’s bankruptcy lawyer serves me a subpoena to show up at the hearing to discuss how much this guy paid us to go to bat with his landlord.
I get up on the stand. The other lawyer asks me to verify an invoice of my firm’s fees. I object to the question since it may violate attorney-client privilege. The judge overrules and orders me to answer. That’s when I say, “No, this is not my invoice.” His attorney is totally baffled, asking me to confirm that the slip has my firm’s logo and address. “Yup,” I say, then reveal that my idiot former client faked the invoice to “prove” the damages.
I could have told the other lawyer all this from the outset, but I wasn’t going to help this former client in any way. So, take note, budding lawyers: make sure your client tells you everything.
5. Honesty Isn’t Always the Best Policy
I cross examined a custom home builder who had a set price contract with the homeowner. The builder said he put 20% more labor/materials into building the home than the contract provided for, so he sued to cover it. I asked him about how he negotiated the price with my client when he volunteers that he knew he couldn’t possibly build it for the price he promised.
This is textbook fraudulent inducement, and buddy had no idea. He just admitted it.
6. The Ice-Cold Truth Spills Out
The plaintiff said a car crash injured him so badly that he couldn’t any work, any regular activities, or pick up his young kids. He then posted a video on his public Facebook profile where he does the Ice Bucket Challenge. If you’re not familiar, he basically lifted a huge cooler filled with ice water over his head. His attorney had no idea he had posted it.
7. The Charges Are Coming From Outside My House
When I was in the military, I was accused of something I didn’t do. At court, the prosecutor described how the investigators staked out my apartment for months. They entered a picture of “my apartment” into evidence. Uh, no? It was my ex wife’s apartment. A place I had NEVER lived (never even spent a single night there).
They asked my lawyer if she objected to the picture. She replied, “I don’t mind them entering it into evidence as long as they change the listing of it.” When they asked what was wrong with the listing, she looked at him and said, “That’s not his apartment.” Because of this, the panel dismissed the case immediately.
8. Cheaters Never Perjure
I handled a fraud case where a man said someone stole his Rolex at a hotel. There was just one problem: there was no proof that he visited a hotel at the time of the “theft.” The guy’s sworn in and immediately slips that he wasn’t at a hotel, but with his mistress. He just left his watch at her house. Apparently, this genius’ wife noticed his absent watch, so he said someone stole it. He hired an attorney and went through this whole circus just so his wife wouldn’t find out about his affair. Needless to say, the insurance company denied his claim.
9. Licensed to Fib
The first case I ever did, opposing counsel misplaced the copy of my client’s driver’s license. Rather than admit their mistake and ask me to resend it, they filed a motion to compel us to send it. In other words, they claimed we never gave it to them in the first place. Well I provided proof that we sent it like eight months ago. The judge did not appreciate their antics.
10. The Camera Adds Ten Lies
I represented a DUI client who swore up and down that he didn’t drink. He said a rookie officer and his trainer pulled him over for a tag violation, then walked back to their car with a body camera still on. On the tape, the trainer says, “Get him out for a DUI,” then the rookie replies, “But he’s not intoxicated.” The trainer demands that he “Do it anyway.” Then the body cam clicks off.
My client sat in custody for three weeks until I finally got the tape. The “oh no” looks from the prosecutor and FTO when the judge saw the tape…I’ll treasure that one. Even better, the judge wrote the police chief a letter saying the FTO was dead to him, and he’d deny every search warrant he tried to bring thereafter for being a liar. Glorious.
11. Numbers Can Be All You Need
I sued a landlord who failed to make serious repairs to low-key force the tenant out. The hard part of these cases is proving bad intent instead of just plain idiocy (intent means you get higher damages). So, I request records from an agency called Code Enforcement. Then I strike gold: the landlord left a voicemail saying to hold off on the fines. He’ll make the repairs as soon as the tenant is forced out. That was an easy case.
12. A Filmmaking Miracle
My brother is an attorney. He had a case where a client said he was permanently disabled from a work accident. At a deposition, my brother overheard the guy talking about remodelling his house, using the money he hadn’t even won in court yet. My brother drove by to see the renovations and saw the apparently disabled client carrying bundles of roofing shingles up a ladder to the roof.
He took a video, made copies, and sent them to the other attorney. The guy dropped the suit and headed back to work.
13. All and All, You’re Just Another Truth in the Wall
I investigated a trade secrets case involving the manufacture of dental wheels used to grind teeth. Niche, I know, but trust me on this one. Basically, there was this family-owned company (let’s call it Company A) that made the best product and treated its employees super well. When the owner of that Company A died, a big international chain (Company B) bought it, took the formula, and manufactured it at their warehouses–except they couldn’t get it to work.
That’s when another company (Company C) comes in, buys the original family-owned factory, and rehires the staff, who start making the product again no problem. Big international company is like, “uh that’s trade secrets violation” and sues. I represented Company C and interviewed all the employees. I ask this sweet old lady how they knew the way to make the product.
Then she drops a bomb. She says, “From the directions on the wall.” Total moment of silence. She looks confused, like we should know this, and explains, “I mean, no one ever looks at ‘em. But there’s a board on the wall with the directions.” We go to the factory and yep, covered in probably 40 years of dust is a board with the entire process on it. When I collected evidence, I took hundreds of photos of this 65+ year old former janitor knocking the dust off the wall. Every picture he smiled for the camera… His FU expression was priceless in every picture.
14. When Oil Strikes You
I had client whose fancy car was ruined by a shop that put in the wrong oil. We couldn’t prove it at first. The engine blew up, oil leaked out, and evidence was lost. I subpoenaed their bank records, figured out they bought their oil from Costco. Called Costco and got their prices for the last two years. I then worked out the amounts they were spending, did some backhand math, and showed based on the values that it was impossible they had ever bought the right oil. They settled in full immediately.
15. The Strong Arm of the Law
This gentleman claimed injuries against his employer after a fall at work. He claimed he couldn’t raise his right arm above his shoulder anymore. First deposition comes along and I’m hired by defendant’s attorney to videotape deposition of the plaintiff. Anyone know THE FIRST THING a court reporter asks you to do in a deposition?
“Please raise your right hand and repeat after me…” Plaintiff raises his right arm above his shoulder with ease and no sign of discomfort. Both attorneys looked down at their notes and neither caught it. After four hours of deposition, where the plaintiff pretends like he can’t raise his arm above shoulder level, I call the defense over and show him the first two minutes of the tape. I got a $5,000 bonus and due to my eagle eye, the judge dismissed the plaintiff’s case with prejudice.
16. A Do-It-Yourself Defense Isn’t the Best Offence
This is so petty but it’s my absolute favorite.
When these clients squabbled over a few inches of land, I had to go up against a lawyer with a reputation for being beyond smug. Part of his case hinged on wheelie bins and how before my client “moved the land boundary” (he didn’t), there wasn’t space to store a full-size bin beside the house. Because a bin could now fit, my client clearly moved the boundary. (This was the extent of his evidence).
During the actual trial, he pulled a fast one by suddenly producing an old aerial photo to show the boundary at the front of the property had also moved. While he argued for it to be admissible, I looked closely and saw that it very clearly showed a wheelie bin in exactly the spot where he said one couldn’t fit. I told the judge we were happy to accept the photo.
That photo did him for nearly 50k in adverse costs. Couldn’t happen to a more deserving chap.
17. The Letter of the Unlawful
We hired a private investigator to track our defendant in a fraud/asset recovery case. Private investigator returned with a photograph of torn pieces of paper that clearly constituted a ripped-up note, albeit in a foreign language. I happened to know said foreign language, so pieced it together and realized it was a letter written by the defendant raging at his accomplice for making highly specific mistakes that screwed him over in the context of our fraud/asset recovery case.
It was unbelievable. The handwriting was a match; plus, the defendant also signed it, and the contents were so specific that it was basically a smoking gun. We almost thought they planted it to throw us off, but the guy was just really stupid. Ran into a bit of a fight re: admissibility but the letter ultimately helped us receive a significant settlement that made our clients extremely happy.
18. Got to Hand it to This Kind of Negligence
My client worked at a meat packing plant. Her glove (they would only give her the loose kind because they were cheaper) got caught in the machine and she lost her arm. We sued the owners and the machine manufacturer for failing to include the required guard. Then we sued the distributor for being in the chain of the sale but didn’t really think they played much of a role. The manufacturer swore they included a hand guard and said the plant owner must have taken it off.
During a deposition, the company showed up with sale documents he should have turned over weeks before. There was a note in small print at the bottom that said the sale was without the hand guard, which is against the law. I pointed it, out and we settled with the distributor. The woman got all her medical bills paid, got money for a prosthetic and got a bunch of pain and suffering damages.
19. A Crime to Remember. Or Not.
I deposed a guy in a large breach of contract/fraud action. I asked him if he’d ever been convicted of a crime and he said no. Late in the deposition, I asked him the question again and he answered No.” I then whipped out his indictment for felony fraud and his conviction for misdemeanor conspiracy. He denied it was him until I started asking about his co-conspirator (his son) and then he gave me the “Oh yeah I remember something about that…”
20. The Rooster Just Got Cooked
I represented Mom in a bitter custody fight. Dad wanted full custody and argued mom was an unfit parent. Mom wanted full custody because Dad had a history of domestic violence towards 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 brought a close family friend as a character witness for Dad, 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. I was able to get the friend to spill the beans that the Dad owned chickens for illegal cock fighting. He also took his young children to these fights, and when the children acted up, he’d punish them by forcing them to feed the chickens, who would peck and scratch them.
I could see the color draining from Dad’s lawyer’s face. Mom got full custody.
21. Done in By the Long Arm of the Paw
I acted for a plumber who ripped up a tile floor to replace a pipe. He installed new tile on top but warned the owners not to walk on it for 48 hours. He emphasized not to let their kids or dogs walk on it either. They walked on it but alleged the defects were caused by improper install. We had an expert do a report, which confirmed that it was consistent with proper installation but people walking on it too soon. Crazy homeowners still went to trial.
In their evidence disclosure, they included a series of pictures. One of the pictures had in the foreground a tile that was tilted upwards. The background very clearly showed a dog’s paw pressing down on the other end of the tile. That wasn’t so much an “I got them” situation as a “they got themselves.”
22. The Funny Bone is Not Admissible in Court
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 (the leg bones are tibia and fibula) to which he only answers “no” then she starts grilling him with questions about the tibula.
After about six questions she asks, “How did you get a medical license and have been able to practice medicine this long if you’ve never treated a tibula fracture?” And begins a small rant about going after his credentials and those that gave it to him, to which he simply responds, “There is no bone named the tibula”. The lawyer became beet red and everyone in the room tried their best to keep from laughing…including the judge. Ouch.
23. Clubbing Yourself Out of a Deal
I represented a plaintiff in a hit and run case. As the plaintiff testifies, I realized that, despite all our prep, she is an absolutely terrible witness for her own case. Like, she couldn’t even identify the street she was crossing when she was hit by the car.
The “oh snap” moment came during cross examination. 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. Defense counsel show the picture to my client and asks her when the picture was taken. Sure enough, they say it was taken the day after the accident when she was supposedly in unbearable pain.
24. Straight Through the Heart, and You’re to Blame
I was a bailiff in a murder case. The first witness testified that she saw the defendant shoot the victim. The second witness stated the same. A police officer testified that he arrived at the scene and saw the defendant holding the gun. The coroner says that the first bullet hit the victim in the arm, the second bullet hit the victim in the torso, and the third bullet hit the victim in the heart, which was the fatal shot.
Defendant yells out, “See that proves that I didn’t kill him! I only shot the guy twice!”
25. Live and Learn, Loudly
In my first year, I represented the 19-year-old child of some rich people in San Mateo County CA. My client went on a shoplifting spree, and I had to clean all her cases up with a global plea (meaning we handled them all at once). Being new, I filled out the plea form wrong, swapping the charges with the please. It’s an easy mistake to make. Every court has their own unique form, and I didn’t have experience with San Mateo’s.
The judge calls my line, starts reading off the plea form, notices the mistake, and then starts screaming at the top of his lungs, “COUNSEL! WHAT IS THIS?! WHAT IS THIS?! IS THIS YOUR FIRST DAY ON THE JOB? THIS IS A COURT IF LAW AND WE DO NOT ACCEPT MISTAKES! FILL THIS PLEA FORM OUT CORRECTLY OR I WILL HAVE YOU TAKEN INTO CUSTODY FOR CONTEMPT!” I did not expect a reaction like that.
My client, who clearly had a huge bong rip at 8 AM and wore an all-pink velvet track suit, looked at me like I was the biggest idiot in the world. After I corrected the plea form, the judge made me wait until the very end of the day. Then he called me up to the bench. In private he told me, “Sorry to ream you like that. Everyone messes the plea form up, so I just pick the youngest lawyer to yell at. Maybe you noticed all the other lawyers fixing their forms? Anyway, gotta do it to keep the calendars running smoothly. Where did you go to law school?” After that he invited me into his office for coffee and gave me some really good life/work advice.
26. All Around Me Are Familiar Faces
I got called for jury duty. At the jury selection phase, they asked if “anyone here thinks they should not…” blah blah. Defendant was in the room. I raised my hand. The defending lawyer looked at me like “Oh, this oughta be good” and asked me to explain. I suggested I tell them in private. He insisted I tell the courtroom.
I said: “OK…I probably shouldn’t be on this jury because I was on a previous jury for this man which returned a guilty verdict.” Lawyer’s face went “oh snap.” After they checked their records, the whole jury was “tainted.” Everyone went home and they had to start over.
27. Convicted with Style
When I was a law student intern, I worked on a drug possession case. Police found drugs in my client’s jacket, but my client said he wasn’t wearing a jacket. In other words, opposing counsel needed to prove the drug-filled jacket belonged to my guy. I had a long meeting with my client where I explained everything and he left happy. On the day of the preliminary hearing, he shows up wearing the exact same jacket that apparently didn’t belong to him.
28. Breaker of (Logic) Chains
I sued an employer for wrongful termination. It went a little something like this.
My rep: So, you terminated him because he was ill.
MR: And he was ill because he’s disabled.
MR: So, you fired someone for being disabled
29. Don’t Bite the Hand That Judges You
I was at a directions hearing with an irritated judge who asked why we were here for such a seemingly pointless litigation (without giving details, he was right). The barrister starts to make our case, as I take notes about areas we need to explore when I hear, “EXCUSE ME, WHY WERE YOU SO RUDE TO ME?” The client, who I told NOT TO COME, was here and furious about the judge’s comments.
She berated the judge for about three minutes, with me and my counsel first stunned and then trying to shut her up, before the judge adjourned the hearing. The case did not go very well, to my client’s surprise and fury. Big sigh.
30. He Didn’t Sign the Crime
My former law partner represented a client who wanted a restraining order against her soon-to-be-ex-husband. As evidence, our client told the judge that when they met to exchange the children for visitation, the ex kicked her. He immediately angrily shouted, “She can’t prove it! I didn’t leave a mark!” Thanks, buddy! 10/10!
31. House Arrest Should Only Punish The Perp…
I was a prosecutor on a case where an 18-year-old defendant applied for bail. He needed a residential address so his dad showed up to confirm that he could stay at the family home. My fellow prosecutor gets up and asks dad, “Do you really want him home?” Dad goes off the deep end. “Jesus. The grief he brought me and his mother. Out all hours. Taking drugs. Hiding stolen property in the garage. All night parties. I’m on anti-depressants. My wife is in crisis.” As the defendant goes back to the cells, he calls out, “Thanks Dad. I owe you one.”
32. This Call Will Cost You
I saw a guy defend himself (not a good idea) against car theft by claiming the cops had the wrong guy. Just one problem: I got his calls from jail, where he described his crimes at length to his girlfriend. The look on his face when I told him I had copies of his jail calls: priceless.
33. You Can’t Lose What You Can’t Have
At a patent dispute case, a large company went hard after a small company, which we defended. Not only did the judge decide that we didn’t infringe on the patents, he invalidated the other company’s patents.
34. You Can Put a Price on Nothing
A contractor ripped off my client. At court, I went through the entire contract and asked the contractor to agree to it line by line. He agreed to the payments for his workers. He agreed to the total. However, he failed to list any profit. My last question was “Where is your profit in this contract?” No answer. As written, he worked for free. Due to this, the judge dismissed the case.
35. Bad Foot Forward
I saw a case where a lawyer described a theft, saying “The footprints make it seem as though he didn’t go to the basement.” The defendant then pipes up, “Actually we did.”
36. Takes One to Not Know One
I sat in on a criminal trial where the defense had no defense other than, “There were documents lying around with the name Jack Smith, and our client’s name is John Smith, so there was obviously someone else living in the house hiding the drugs.” In the very last minute of closing arguments, the prosecutor stood up and dropped the mic.
“I’m really tired of you spending all week pretending you don’t know who Jack is when you know very well. Your trial binders which have been sat on your desk all week say Jack Smith, because that’s what he goes by.”
37. Get Up to Speed
I prosecuted a traffic ticket and ended my opening statement with something like, “By the end of the day, you’ll agree that the officer caught the defendant going 65 in a 50.” The defendant, representing himself, stands up and says, “While he may have clocked me going 65 in a 50…” The judge stops the trial, excuses the jury, and says,”You just confessed soooooo… Can you change your plea to no contest or what?”
38. Quit While You’re Far, Far Behind
Eight months into a case, 12 hours into a deposition, opposing counsel’s client stood up and changed everything. He said, “I’m sick of this. I made it all up.”
39. The Honest Thief
I work fraud investigations. I called a suspect who allegedly used money for an incapable individual. I explained the allegation. He stated: “Yeah, they’re correct. I took the lump sum and bought cocaine and booze. I understand it’s wrong, do what you gotta so. I’ll sign a statement or come in the office if you need me to.” I don’t really deal with high level criminals.
40. Bent Out of Shape
I busted a bunch of people for faking disabilities by hiring private investigators to tail them for a day. One guy claimed he could barely walk. I caught him literally jogging out of his independent medical examination. Also got photos of him throwing his walker aside when he bent down to pick up his keys after dropping them.
41. Little Miss With Big Secrets
My buddy’s divorce lawyer withheld all of the proof of infidelity and other stuff (1+ year of Messages history dumped through some app, provided to my buddy by the guy who was banging his wife) until the last part of the negotiations.
Then the lawyer dropped the bomb that they had proof of her doing all of this insane stuff, including fabricating a rape story when she got caught cheating. (She also got her uncle, a DA, involved with that story). The family was stunned, and her parents were in the room when it happened. Oh, and her cousin represented her. She was very much a “daddy’s little girl” type and as a result her parents never thought she could be in the wrong… meanwhile their daughter is a serial cheater, drug addict buying painkillers on Silk Road, habitual liar, and overall horrid person.
In conclusion, my buddy walked away from that divorce scot-free.
42. Say What You Mean, Mean What You Say
I was in an accident a few years ago. The guy who hit me got a ticket for an unsafe left turn, and I got a ticket because I wasn’t wearing my seatbelt. When I looked closely, I realized that I didn’t need a lawyer: I’d be able to defend myself against this cop no problem. In the section on the ticket, the cop inadvertently wrote “Did wear seatbelt while operating the motor vehicle” instead of “did not.” When I got to court, the judge asked how I wanted to plead.
I asked the judge if I could clarify something first, and he said “Sure”. I stated that “The ticket says I did wear my seatbelt while operating my motor vehicle. If that’s the case, I want to plead guilty.” The judge looks down at the ticket, looks back at me, and says “Case dismissed! Have a good day!”
43. Don’t Stop Believing
My dad is out of state on business driving through some no-name town when he goes through an intersection. Suddenly, a cop pulls him over and tickets him—stating that he ran a stop sign. My dad insisted that there was not any stop sign, but the cop did not listen. Pissed, he went back to the intersection and saw that there was indeed a stop sign hidden behind a tree and twisted in the wrong direction!
Even more pissed, he went into a convenience store and bought a disposable camera. The clerk laughed because he saw what happened and knew what was up. Luckily, my dad had to be back there in a few weeks for work. The cop assumed that someone with out of state plates would just pay the ticket, and was shocked when my dad turned up in court, ready to be the best amateur lawyer ever.
He calmly presented his evidence to the judge, and strolled out in five minutes scot-free.
44. Well, I Guess He Walked Right Into That One…
My lawyer dad had a person come in and 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 scumbag 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.