With all the stereotypes of dishonesty, greed and questionable morality, lawyers definitely get a bad rap. Though there may be some truth to these prejudices, lawyers aren't all bad people. There are many good souls in courtrooms, doling out justice where it's most needed. However, even a good lawyer can wind up defending a less-than-ideal client.
Let’s lawyer up and get down to these jaw-dropping courtroom stories, all told by good people with heinous regrets.
1. Physical Rehab
A guy lost his wife and children in a car accident. He wanted to exercise to get his emotions and mental health back in check. The doctor wrote him recommendations for exercise equipment and he submitted the expenses for the same to his insurer. My client (the insurer) wanted this fought tooth and nail because exercise equipment was only covered for physical rehab and technically, the man was not physically injured.
I do not practice in this area anymore.
2. The Power Of Money
We settled a case for several million dollars for a girl’s father, who passed. The mother, who was divorced from the father, tried every way possible to get the money, but it was placed into a blocked account until the girl turned 18 years old. The DAY she turned 18, mom told her they were going to transfer the money to a "better account."
Mom transferred it to her own account and fled the country WITHOUT the daughter. Screwed her own kid over for money, and essentially made her kid an orphan. Money does horrible things to people.
3. No Compensation
I’m a worker’s compensation attorney. I now represent injured people, but used to work on the other side. This is the case that made me switch. There was an applicant who fell off a ladder, busted his back, got his shoulder messed up, and needed years of treatment. He had physical and psychological issues. The poor guy was really messed up, so he went to court to get permanent disability payments from my client. We were five years into the lawsuit and finally getting to settlement time.
If we bought out his future medical, the settlement would be pretty far into six figures, which is a lot, but keep in mind that this guy was the sole provider for wife and two young kids. Then we made a jaw-dropping discovery. We found out that the man had aggressive brain cancer. He would only live for a couple more years, at best.
Thus, my client wouldn’t have to pay him for very long. In the end, the man did get disability pay for $60k-ish per year. But because he'd only get that one check, what should have been millions was much, much less. I felt terrible for the guy and his family. I tried to get my client, the insurance company, to agree to a more humane amount given the circumstances, but the bean counters said heck no.
The attorney knew it wasn’t me making the decision. Even though he worked on that guy’s file for 5+ years he decided to take $0 in fees. I have so much respect for that attorney turning down $10k+ in fees to help his client in a very sad situation.
4. Spinal Injury
I shadowed on a personal injury case. Their client was drinking in one of our guy's bars and gets wasted, becomes abusive to staff and then storms out, falling down the stairs. This resulted in a C6 ASIA B incomplete spinal injury—a severe loss of mobility and sensation. His people sue, and we force them to accept contributory negligence and personal liability.
He gets an okay payout that covers his lawyer's fees and immediate needs and is left disabled. Even if it was seen to be his fault it was still hard thinking that his life will never be the same just because of one rowdy night. Spinal injury care is massively expensive and the money he received wouldn't be sufficient for his whole life.
5. Flu Shot
To this day this case amazes me. As a first-year associate, I was given a terrible insurance case where my client received a flu shot and thereafter felt pain in his shoulder. He went to another doctor who performed an MRI and determined that he had a torn rotator cuff. Even though these things were almost certainly not related, my job was to argue that the flu shot caused the rotator cuff tear.
Even so, our doctor witness somehow connected the two and the case paid out. Being the bottom of the totem pole, I had no choice but to take the case—which was handed down by a partner. But at the same time, it just overwhelmingly made me feel like the worst stereotyped attorney. I hated having to walk into court with such a corrupt argument. I could feel my reputation being destroyed in real time.
6. The Veteran
I used to represent veterans to get their service-connected disability benefits. I represented a homeless veteran who told me that he had been stationed in a certain conflict zone. Everything he said corroborated with the timeline and how events played out, and the story barely changed so I took him at face value. I argued to get him compensation for his PTSD with the earliest effective date possible. Then I expedited the hearing due to his homeless status. I got him six figures and off the streets for a while.
I went to town for this guy and worked hard to make sure he got a good result. But then, I learned the real story. The man's full records finally came in two long years after I had first requested them. It turns out that the man had been in the forces, but he had never served in the zone that he said traumatized him. In fact, he never served overseas at all. Kind of burned me out after that.
7. Family Or Furniture
I did a divorce where the husband (who I was representing) wanted to trade custody of his children for a set of bedroom furniture. The bedroom furniture was not even like a family heirloom. It was furniture that you could probably get at a Rooms-to-Go or something. Ugh, even thinking of that guy still makes me ill. That's why I got out of family law.
8. Archaic Jury
I'm a paralegal, not a lawyer. I worked very closely on a case where the client had brutally forced themselves on their spouse. It was clear from the beginning that the client was mentally unstable and very capable of doing this same type of thing again. We ended up winning because the victim was a young woman, her demeanor during the trial was atrocious, and the jury was all older men. Awful.
9. Rich Parents
I got a spoiled brat of a teenager cleared of a shoplifting charge when he absolutely had done it. His rich parents hired me to represent him. I did that to the best of my ability, and we went to trial and won, but I can't say I felt good about it. This kid needed to be taught some accountability for his actions and his parents just wanted to buy their way out of any trouble he got into.
10. No Prosecution
One time, I represented this client first when he was a juvenile charged with disorderly conduct at school for fighting, then when he became an adult, it was for simple things like possession. As he got older, it became easier and easier to figure out what parts of his life hadn’t gone well. Over the years, I tried to counsel him and push him to better himself.
When he got his high school diploma, he started going to Narcotics Anonymous, started classes at a community college, and found a part-time job. Then, on the night of his 21st birthday, he was charged with driving while impaired. Of course, I take on this case for him. But about 6 months later, when we're supposed to be in court, my client doesn't show up. At this point in his life, this was highly unusual.
As I’m trying to figure out where he is, the court starts going over Arraignments and First Appearances. Lo and behold, three people are up for murder charges. The prosecution starts to tell the judge about the facts of the case. During his speech, he mentions the victims' names. That's when I felt my stomach drop. One of the victims was my client.
Apparently, my client was at a party when these three individuals decided to allegedly do a drive by shooting. My client suffered multiple wounds and didn’t make it to the hospital. So...by default, as you can’t prosecute someone who isn't alive. Thus the State has to take a dismissal which means that technically I won my case.
Either way, it was crushing. My client was finally turning his life around...only to pass before he could enjoy it.
11. Taking Its Toll
As a former employment lawyer, I regret defending a company in a lawsuit in which their employee had an accident, lost her left leg, and had the left side of her body covered in burn scars—with the company at fault. The case was more or less like this. This lady worked at a toll booth on a highway. Whenever she needed to go to the toilet, she'd have to close the toll and change the sign lights to red so no one would go through that toll.
Unfortunately, due to lack of maintenance, one day, the lights did not change. The results were catastrophic. As the lady was crossing the road, a car ran her over and dragged her for 10 excruciating meters. After defending this case and this horrible company, I realized that I no longer wanted to do this kind of work. I dropped everything and quit the week after.
12. Unsafe Roads
The case I particularly hated happened at my first law job. This woman was a long-term client of my boss. In the past ten years or so, she has been caught driving while impaired eight times, violated home incarceration countless times, been caught with controlled substances a few times, and even attacked two people while she was supposed to be confined to her home
My boss at the time was the master of getting people off for these kinds of charges, so this client always managed to stay on home incarceration with whatever releases she desired. I always regretted her cases because that woman is truly a danger to the public. She’s undoubtedly going to end someone's life someday. But lord almighty, if she isn’t the luckiest woman alive in getting away with reckless driving so far...
13. No Lesson Learned
In one of my first cases after passing the bar exam, a young man retained me on a drunk driving charge. No one was hurt, but he totalled his car. During trial, the officer testified that my client was clearly wasted at the scene of the accident, and that my client was loudly blaming the accident on the idiot who took his car, crashed it, and then fled before law enforcement arrived.
However, according to two other witness statements, my client's friend (the passenger) was the one blaming a mystery stranger, not my client. The officer must have confused the two men during his testimony. This discrepancy raised a reasonable doubt in the judge’s mind, so she acquitted my client. Looking back, I wish she hadn't.
At the time, the acquittal was somewhat unexpected for me. In my personal view, my client was clearly responsible for the accident, regardless of who was blaming the mystery idiot to the officers. But I was happy my young client got off, no one was hurt, and lessons were learned. And I was quite euphoric to have won my first big case.
The regret? About a month after the acquittal, my young client called me at 3 am from the local detainment center saying, “It’s me again! The authorities got me again! Can you help me?” Not only did I answer no, I instantly regretted getting the earlier acquittal. My client apparently didn’t learn any lessons...
14. Cover Up
I convicted a father for killing his wife. Then, years later I found out the awful truth. It turns out that the father was lying when he confessed. He was actually covering for his teenage son, who actually been the one who attacked the mother. In the years between the conviction and my discovery, the son took his own life and the father was content to serve his time in prison.
15. Dog Trial
Family law is a little different, in that you never really "win" per se. You may get more favorable rulings or better terms, but unless the opposing party did something mindbogglingly stupid it's never a decisive "win" really. Although I did have a case where my client fought really hard for the dog, and then ended up turning him over to a shelter. Freaking jerk. The ex-wife received an "anonymous" tip and was able to get him back quickly.
16. Rotten To The Core
I worked in defense and represented a guy who had been driving while impaired. Long story short, he was pulled over by law enforcement after they followed him leaving a bar. At trial, I got the one of the officers to admit that during the 2.5 miles he followed my client for, he did not observe a single moving violation—no speeding, erratic driving, driving over the lines, blowing stop signs, running red lights. He didn’t even “stop suddenly” at red lights.
I also got the DRE officer to testify that the accused only spoke Spanish and they couldn’t get an interpreter officer to the roadside to explain the field sobriety exercises, which the officers documented the accused “refused to perform.” Jury came back in 15 minutes. The guy was extremely grateful, and his lovely family was very gracious in thanking me and our office. Felt good about the whole thing. Then everything went so, so wrong.
A couple months later, I’m in the county to meet with a client, and I see him in one of the pods. I find out that sometime after the trial he inappropriately touched his 8-year-old step-daughter. I think about that case a lot.
17. Telling Tattoo
I helped a man regain visitation of his child after a year or so behind bars. I thought I was a great humanitarian. Oh, the hubris that comes from being a baby attorney! As we were having a chinwag after court, waiting for his ride, he showed me his tattoo: a giant symbol to show his dedication to the White Resistance. I’m a blue-eyed blonde, so I guess he thought I was down with the cause. I went home and threw up.
18. No Protection
Not my case, but a former associate of mine won a restraining order hearing where he represented the person who the order would have been against, AKA not the victim. The victim's request to put a restraining order on his client was denied, and like 2 months later the guy put the victim in the hospital. That one still bothers him.
19. Real Estate Litigation
After law school, I had to turn down an amazing job offer because my wife got a better offer somewhere else. So basically, I followed her along and was desperate to find something. After three months of fruitless efforts, I would take just about any job that required a JD. Three months after moving, I got an interview for a "real estate litigation" job.
They hired me the next day, looking back that was probably red flag number one. First day on the job they taught me how to foreclose on a claim of lien. These are two things I had never heard of before. Turns out, it is totally brainless work if you have the right forms . So anyways, it took me about two months to realize this (when I had my first set of hearings) but literally my sole purpose at the firm (which represented over 100 Home Owners Associations) was to take people's houses away for not paying their Home Owner's Association dues.
After my first set of foreclosures, I actually slipped into a pretty legitimate depression. I was getting paid peanuts to drive nearly an hour to work every day, to do work I despised, on behalf of people I literally could not pretend to care about. Then came the straw that broke the camel’s back. I started signing the foreclosures and one day I realized I was THAT GUY. I understand someone has to do the work I guess—there certainly is a lot of money to be made—but it was not for me.
I did that job for three months, came home one Friday, and told my wife I'd rather be homeless than go back on Monday. By some stroke of luck, I started a stellar defense job within two weeks and all of the heartache has 100% been worth it. I've won a lot of cases and never once felt bad about it. Never lost sleep over someone not going behind bars.
So yeah, every case where I took someone's house away (probably two dozen times) for not paying HOA fees (generally $4,000 or less) was the worst case I ever won. Screw those.
20. Big Regrets
I did some custody work early in my career and won some cases—more on the merit of my trial skills than on the merit of the parents. The thing with family law work in general is that there is essentially no bar to entry. Anybody with a law degree and a pulse can get a family law practice up and running quickly because there is just an absolute glut of work.
What that also means is that 75% of the lawyers practicing family law are clueless and awful. Early in my career I certainly was clueless, but at the least I was not awful. Therefore, in a battle between clueless and awful versus just clueless, clueless usually won. So yeah, I can't recall any specific cases, except to say that fighting over children in court is a terrible thing and basically everyone loses. I regret that entire portion of my career.
21. Another Custody Case
A woman wanted her daughter’s custody. We used the state preference about custody going to the mother (judge bias), her improved economic situation, and some minor garbage like the daughter’s grades and discipline problems at school to discredit the dad. Not even a month after we won, the mother calls and says she had a ''problem."
Then she explains the ''problem'' was that her boyfriend forced himself on the girl, and after that she had the gall to ask that we pick up HIS defense. It was one of the things that made me want to quit government work.
22. Don’t Look A Gift Horse In The Mouth
Summer of 2018, I get work regarding what seemed from the client's description—a pretty drawn out and messy divorce case. The husband was my client, and he made it seem, very adamantly, that his soon to be ex-wife was after his every penny. Given; he appeared to have a fairly high paying job, it looked like a pretty common type of case, the city I work in has many instances of this, it has a high cost of living and a lot of well-paid working professionals in private industry.
He was a very well spoken, amicable guy in his late 50s, and truly seemed like he'd been taken by surprise and betrayed by his soon to be ex-wife. When I actually got to the case, however, I was basically floored. His wife was a working professional as well (worked in government), they'd been married for over twenty years and had two kids together, and a paid off house.
Before taxes he made almost three times what she did, not counting his stock options, and yet she'd contributed equally to their mortgage on every home they'd owned over the course of the marriage. By all accounts, despite a vast difference in income, she'd carried her weight, raised two kids, and worked full time during the entirety of the marriage.
I live and work in Canada, she could have easily raked him over the coals in the divorce if it had gone to court. Instead, it seemed like she'd done everything she possibly could to not have him subjected to that. This divorce had been ongoing for five years before he hired me, and it was basically him looking a gift horse in the mouth over and over, a constant renegotiation on the contract they'd both signed initially, with him skimping on alimony and then debating on lesser terms.
He was basically given an inch and tried to take a mile, dragging it out for so long that per divorce law it had to go to court. I almost suspect he did so as a way to try and drag her through the mud, though he may have genuinely been that delusional. I consider it a win only because his ex-wife was adamant about only wanting what was somewhat fair, and for it to be over because of the strain it was having on the family.
Per the contract he owed her, there was about 50,000 in backpay, but she was content with 15,000, which was less than this guy made in a month. I did regret the "win" though, because she seemed like a very nice woman with the patience of a saint, while almost all of his anger towards her seemed to come from a wounded ego.
23. Twenty Years
I prosecuted a murder case. 21-year-old kid starts dating an older guy's ex-girlfriend. The older guy, a real biker dude, was going all over his small town talking about how he was going to kick the kid's butt. The older guy sends some inappropriate pictures of the ex while he's getting drunk at a bar, so the kid says something smart in response. Older guy comes to the kid's house to fight him.
The kid shoots him once, and the older guy doesn’t survive. Jury didn't buy self-defense or castle doctrine. Convicted of voluntary manslaughter. Twenty years. Burned up his appeals with no luck. I have a son about the kid's age. I could totally imagine him doing the exact same things if he were in a similar situation. It's going to haunt me forever. No doubt about it. Started thinking about other jobs the moment the verdict came back.
24. Big Hearts, Bigger Stomachs
Not really “winning” but I recently had a case settle where my client was so obviously lying it was painful. He was in a fender bender and said he was too disabled to drive, or to work at the office as a result. He then claimed that his employer fired him after he had been on disability leave for almost a year. Some really big claims.
A few months after filing, we discovered that he played in a national, amateur, full-contact football league and there was footage of him getting tackled, endzone dancing, and tackling during the time he claimed he was too hurt to sit at a desk. Even when I confronted him on it, he claimed he hadn’t played while he was injured—despite having a stat line and footage of him playing from games dated on days he was supposedly getting physical therapy.
We didn’t settle for as much as most of my cases, but he still walked away with like $20k. I’m happy to be a plaintiff’s attorney for the most part because my clients have typically been wronged but he was such a bald-faced liar it really made me angry.
25. No Rest For The Wicked
I was representing the government at a social benefits tribunal. The applicant was an autistic man who was struggling to make ends meet, but was trying his absolute best to contribute everything he could to society. He had a job where his manager was very accommodating and was a very sympathetic person. He just wanted the extra cash to make his life a little easier for himself.
Sadly, he didn't qualify for the benefit, but I think he deserved it. My closing argument was that no matter how much we empathized with this man, no matter how deserving we thought he was, he simply didn't qualify and the tribunal had to apply the law. He was unsuccessful, and when I left the building to head back to my office, he was just sitting outside on the curb crying. That image has stuck with me for a few years. Pretty heartbreaking.
That was the lowest point in my career and I have moved on. It's really important to remember that mental health in my line of work is a very real issue that is hurting people. There aren't sufficient supports in place to help people like me and many others who find themselves in positions like this.
26. Cashing Out
I settled a personal injury case for a guy and he was set to get about $5,000. He was behind bars at the time. I held the money for a couple months and when he got out, he came by to get the money without delay. The next day, the authorities came around and asked if I knew him. I explained that I did. I was told he passed that night of an overdose and the only thing found on him was my card, some substances he had not yet used, and a needle.
27. Parole Corruption
In the spring of 2018, I was a third-year practicing intern at a public defender's office. As the job entailed, I dealt with a lot of clients who were facing time, but none stuck in my mind the way this one guy did. One day, I looked over the file where the client had three years of probation. I found this very odd due to the initial charge: Possession.
Even so, I go to the docket call and to talk to my client. He's a white male, 30-35-years-old. The first words out of his mouth were "$600." I didn't know what that meant or what was going on. So, I asked him. What I quickly learned was that this client was mentally impaired. During our conversation, he kept bringing up the fact that he didn't do anything, and that he is "paying, paying every month" etc.
And, probably due to my lack of experience, I kept trying to steer him towards the issue: Why did he violate his probation conditions? It didn't even cross my mind that, hold on, maybe he didn't actually do it. I left the cell, talked with the public defender, and told him about the situation. After our conversation, I realized what the client was trying to say.
He had fees of over $2000 and all he had left to pay was $600. If you don't pay, you are in violation of your parole and you have to go back in the slammer. So, in his mind, he thought he was there because he hadn't paid n full. The reality was much worse and different. After a mini investigation, I determined it was the half-way house where he resided.
I contacted the wonderful old woman who "ran it" if you will. She gave me details that this man, although he knew, could not regurgitate and express. Turns out his parole officer was a complete scum bag. He had gone to the half-way house, told our client what a piece of garbage he was, and how he was a total waste of DNA.
He proceeded to go into the kitchen and bring out his service weapon. Then, he ordered my client to go into the back yard and literally dig a grave for himself. All of this was done in front of the old lady. On the day of the case, I called and she immediately came to testify for him. The judge dismissed the case. Found out later, the parole officer was doing this kind of thing to multiple people. He got fired immediately.
28. What Money?
I represented this construction worker in a divorce. The wife stayed at home with the kids and had no money. Through entire divorce her attorney claimed that my client was hiding money. They had no evidence and the client vehemently denied it. We had a good settlement in the case and I considered it done. When the client came in a few weeks later to pick his file, he thanked me for my work and said, “And she never did find the money I hid!” He had a big laugh and walked away. What a loser.
I helped represent a slumlord in a lawsuit regarding discrimination in public housing based on disability. The state was representing the disabled tenant. The facts were pretty clear, the slumlord discriminated on the basis of disability. However, our state doesn’t have much case law regarding discrimination in housing based on disability.
We ended up sowing enough doubt to survive the tenant’s motion for summary judgment. Knowing that the tenant needed money, we made an offer for a decent amount of money for a disabled tenant, but peanuts for the slumlord. I imagine the state wanted to proceed to trial, but the tenant desperately needed money and accepted.
By gaining the best outcome for our client, we allowed the slumlord to get off basically scot-free.
30. True Story
A guy was a convicted felon so couldn’t be in possession of any arms. So he sold two firearms to a pawn shop, only for them to later traced back to him because of the store's paperwork. The felon's story was that they were his father-in-law's and that he and his girlfriend had only found them after he passed. They sold them because they wanted to get rid of them and they needed the money.
The DA office refused to waive the three-year minimum sentence, so it went to trial. I was the prosecutor for the case and ultimately I got a guilty verdict, meaning the guy had to spend three long years behind bars. I felt bad because I think his story was true. I did my job...but at what cost? A guy who made an honest mistake got locked up for three years of his life. That one keeps me up at night.
31. Doubtful Justice
I had a divorce case where I represented a wife who was livid because her husband left her for another woman. The wife reported that their young daughter made a comment about something that could be interpreted as inappropriate touching by her father, the husband. The only conceivable corroboration about the comment would have come from the daughter’s testimony.
However, the daughter was so young that her credibility would be suspect, and nobody wanted to put her through the ordeal of testifying against her father. There was no possibility of prosecuting the father, because there was no other evidence that he'd mistreated the daughter. But the wife pushed for sole custody and insisted that the father would only get supervised visitations for the next year.
We/she won. I’ll never know for sure what happened between the father and daughter, but the more I think about in retrospect, the more I doubt that justice was served.
32. Malpractice In The Court
I once represented an insurance company in an awful case. A man had a brain injury due to a car accident, and passed six months later. His family sued my client. I've never seen a lazier effort on behalf of a plaintiff. His firm immediately handed the case over to a junior associate. She barely did anything with it. We had settlement negotiations but they were way too high considering the lack of any medical evidence they had to link his demise to the car accident.
It probably was related, but you can't walk into court with that argument and no evidence to support it. That seemed to be their plan. On the eve of trial, I told the other side's lawyer to accept the settlement but she refused. I told her she would lose because I was going to get all of her "evidence" thrown out. Still, they went to trial.
The partner that was supposed to be there with her, but he didn't show up because his dog was sick. No joke. As I predicted, all of her evidence was thrown out. The family was sobbing as the case devolved. In the end, my firm won but I didn't feel great about it. The judge was appalled. I'm sure the firm was sued for malpractice. The young associate got fired within weeks.
33. Brain Matter
I came into law school with a very clear moral compass. I knew what I wanted to do (defense) and I had very strong feelings about capital punishment. I thought there was never a situation that warranted it. Cut to me working in my school’s Capital Punishment clinic. The way the clinic worked, was that you'd typically be assigned 1-2 clients, review their case, visit them, and do research at the discretion of the supervising attorneys. I had one client, and his case will haunt me for the rest of my life.
He goes in for life after a really brutal assault on a teenager during a burglary... and proceeds to move to more and more secure facilities after numerous attacks on guards and an escape attempt. But that wasn't what got him capital punishment. See, while my guy was in supermax, he managed to slip his cuffs, beat a guard lifeless with a metal bar, and throw his battered corpse down the stairs.
All of this is on video. There's no question he did it. So, the jury deliberates for like a day before they give him the long goodbye. By the time I get the case, it's about reviewing his eligibility for capital punishment. So, I dig into his case file for the testimony that appeared at trial and there's all this stuff about huge problems with his cognitive ability and like his actual brain structure.
With the supervising lawyer's okay, I do a little independent research, consolidate all the different testimony and map it onto a brain. The conclusion I come to is pretty simple but completely shocking. This guy has less than half a brain. Through a combination of substance use, a rough upbringing, and birth defects, roughly half of my client's brain just is not present anymore in any meaningful way.
Including all the centers that regulate hormone production, fight or flight response, and threat assessment. I find a bunch of medical reports where people with just some of these conditions get severe behavior imbalances, and in at least one case psychotic episodes. Basically, I help establish that this guy has the kind of diminished capacity that makes him ineligible for Capital Punishment under Atkins.
If he's successful on an Atkins claim, then he is structurally ineligible for capital punishment. But, do I feel good about helping to probably save this guy’s life? Heck no. Because it means he's going to be in a supermax forever and he's already shown that he can harm people in a supermax. If he doesn't get the chair, he'll still be in prison for life, and I can almost guarantee that he will injure (or worse) another guard during that time, probably multiple ones.
BUT if he's executed, we're executing someone who really isn't meaningfully responsible for their actions because most of their brain is gone. He never had the option to make the right decision, or make any decision, because of his incredibly extensive brain damage. It's out of my hands now, but they are appealing so it's going to go before the court eventually.
I drank a lot that semester, and I'll never do capital punishment work again.
34. Mental Scars
This is my nastiest case by far. There was a guy in the UK who came from Zimbabwe. He lived here for three years from the age of 16 and then went abroad to serve in the British forces. When he returned from service, he got himself a girlfriend. One night, he went to her apartment and found items that would suggest she had more than one partner.
After a heated argument, she admits that she's selling her body. He's so furious that he strangles her. He runs off to Heathrow Airport to catch the first plane to Zimbabwe and is caught by the authorities. He claimed that he had his passport on him because of pure chance, and the reason why he was going back to Zimbabwe was so he could end his own life at his grandfather's grave in shame.
The cases against him were to A) imprison him or B) boot him out of the country. He got imprisoned but we were called in for the second case as I was with an immigration firm then. We won the appeal. Twice. On the grounds that he was mentally scarred by his time in combat, his officer gave him an amazing report and that British guys with service records don't get the best treatment in Zimbabwean prisons.
Now he walks the streets as a result of good behavior. This has always been... a weird case. He was definitely supposed to have been kicked out of the country for his grievous actions. But human rights are human rights...
35. Saw Situation
When my uncle was a young personal injury lawyer and had to take all the cases assigned to him, he had a client who was drinking with his neighbors on someone's front porch. It was a spontaneous get together and he got quite toasted. The client starts talking about his amazing new portable saw he just bought. He brings it out to demonstrate, propping up a board against the porch stair and his thigh. He proceeds to cut himself so badly that his junk was hanging on by a thread.
So, my relative has this guy in to chat, and he says he wants to sue the whole world: the maker of the saw, the store that sold it and the neighbor whose porch he was on. He unexpectedly drops his pants right then and there to show the damage. He refused to accept any blame for it. And I always thought lawyers had boring jobs.
36. Doctor’s Defense
I work in medical malpractice defense. Once I had an obstetrician who burned a patient during a procedure. For the next 16 months, whenever I met with the doctor, he lied to me, saying he had no idea how it happened. But the patient came in without a burn, and after the procedure, the patient left with a burn exactly where the doctor had been operating.
There's no way this doctor didn't know what had happened. It wasn't until I brought up settlement, because by that point, I knew we weren't going to win, that he finally admitted, "Oh maybe I do know what happened." We ultimately settled that case, but sometimes I think this doctor really ought to have lost both the lawsuit and their license.
37. Fees On Fees
I once worked on a case where, if the plaintiff won, my client (the defendant) would have to pay his accuser's attorneys’ fees. Thankfully, at trial, the judge agreed with our case and my client won. So far, so good. But then the plaintiff appeals all the way to the state’s high court, requiring a ton of briefing and time.
High court agrees with plaintiff, reverses and sends back to the trial court, which now enters judgement against the defendant for a few thousand in damages against the plaintiff, and tens and tens of thousands of dollars in attorney’s fees from the appeal. My entire firm regretted "winning" that case.
38. No Pay
When I was a young associate, I was assigned to do a civil commercial trial for a client that was not happy with the senior partner. He stopped paying. We moved to withdraw. The court refused to allow us to withdraw and forced us to go to trial. We spend a significant amount of time in trial prep., etc. I win the trial.
Client never pays. The client's position was that my boss screwed up the deal and that there never should have been a dispute/trial to begin with. Firm policy prohibits us from suing clients because that causes a drastic increase in malpractice premiums—9 times out of 10 if you sue a client for nonpayment, they will countersue for malpractice. All in all, technically I won. But the entire case was a mess and the client didn't even pay.
39. Accumulating Bills
I won a summary judgment motion that my firm fully expected to lose. We had a decent argument, but odds were stacked against us. For the uninitiated, a summary judgement motion is a time in the lawsuit when each side thinks they know all the facts there are to discover about the claim and the various defenses that will be brought up.
One party (usually the defendant) says, "Based on all these facts, even if they're true, I still win because plaintiff can't prove his case." You file a motion asking the judge to review all the facts. This is not a trial and doesn't have witnesses. It's all done on paper, reviewing expert reports or witnesses' under oath deposition testimony, taken usually months prior.
You ask the judge to say, "Yes all these things are true, but it is not enough to show a violation of the law, party filing the motion wins." And you do not proceed to a trial. Do not pass go. Do not collect your contingency fee. That's a lawyer joke...a contingency fee is what sometimes winning lawyers get paid only when they win.
Anyway, the client initially was thrilled. Case is over—we tried to break the news gently... nope. Three years later we're back in the same spot we were before we "won" our motion. The other side appealed it up to the state supreme court and won. So, we are back at square one. North of $100k in bills for his lawyer, with no resolution. Maybe it'll settle, maybe it will go to trial.
40. Scot Free
I have been a defense lawyer for 30 years. I have tried over 100 violent cases and 20 capital cases, but here's the one that stuck with me. I had a case very early in my career where I defended a man who was being accused of ending a young man's life. In the end, the jury was hung and my client was acquitted at his second trial. I was doing my job, but I had this suspicion that my client's story wasn't completely honest.
As we left the courthouse, he was walking one way, and I another. I yelled back and asked, “ You shot that guy didn’t you?” He said, “Yep!” and laughed. I have never asked a client if they were actually guilty since hearing that man's laugh. It bothered me for quite a while.
41. Relapse Regrets
I do family law. I once represented a father who had lost almost all custody of his kids because he'd had issues with illicit substances and had spent time behind bars. He came to me saying he had been clean for nine months and had his life together. He seemed so sincere in wanting to get a full relationship with his son. Meanwhile, the other side fought viciously to keep him away. After a long trial, we prevailed and my client got fairly frequent unsupervised partial custody.
Only about three months after the case, everything unraveled. The father was back doing drugs and selling all his stuff for more money. But for me the most soul-crushing thing is that he set up a fake GoFundMe stuff for his child's "cancer." His child didn't have cancer and has never had cancer, so you know where that money was going.
I withdrew from the case at this point so I don't know what happened afterward, but I imagine and hope his custody was taken away. Basically, the net result of winning the case was that the poor boy had to witness his father relapse and then get exploited by his own dad for money. Definitely the worst case I ever "won."
42. Hard Business
I had this happen to me twice. Got my client out on bail, only for him to leave the court and immediately get attacked so brutally that he didn't survive. The first time, my client got chased by law enforcement, then a struggle ensued, and my client ended up with a bullet in the head. His mother told me that it was my fault that it happened. The second time, a young man no more than 16 years old got released while awaiting his trial.
One of the conditions of release was that he maintain a curfew. The exact same night that he got bail, my client broke curfew, went over to somebody else’s house and lost his life in a substance-related theft. The mother blamed me and said that the devil was working through me and that we were all demons. Not my best days on the job.