"This Is Going To Haunt Me Until I Die." Lawyers Are Revealing The Cases They Regret Winning, And It's Heartbreaking
Warning: This post contains mentions of sexual abuse and drug use.A while back, Redditor u/ahtemsah asked lawyers,
Warning: This post contains mentions of sexual abuse and drug use.
A while back, Redditor u/ahtemsah asked lawyers, "What's a case you regretted winning?" Lawyers shared why they have big regrets over winning a case, and it'll actually surprise you. Here are the shocking results:
1."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, still makes me ill. That's why I got out of family law."
2."I prosecuted a murder case. A 21-year-old kid starts dating an older guy's ex-girlfriend. The older guy (real roughneck, loose connections with a local biker gang) was going all over his small town, talking about how he was going to kick the kid's ass. The older guy sends some nudes of the ex while he's getting drunk at a bar, so the kid says something smart in response. The older guy comes to the kid's house to fight him. The kid shoots him once, and the older guy dies. The jury didn't buy self-defense or castle doctrine. He was 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. This is going to haunt me until I die. No doubt about it. Started thinking about other work the moment the verdict came back."
3."I’m a work comp attorney. Now, I represent injured people, but I used to work on the other side in insurance defense. There was an applicant with a serious injury. Fell off a ladder, busted his back with fusion, shoulder messed up, and years of treatment. Internal issues, psych issues — really just messed up. He had 50%+ permanent disability. We were five years in and finally getting to settlement time. If we bought out his future medical, the settlement was pretty far into six figures. This guy was the sole provider for his wife and two kids. Then, we found out he had an aggressive brain cancer. He was expected to live only for a couple of years, at best. Thus, we wouldn’t buy out future medical anymore. Still got permanent disability for around $60K, but couldn’t give medical buyout based on 25+ year life expectancy anymore."
"I felt terrible for the guy and his family. The adjuster and I tried to get insurance to agree to some sort of amount, like, a five-year buyout, but the bean counters said hell no. The attorney knew it wasn’t me making the decision. Even though he worked on that guy’s file for over five 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 messy situation."
4."I regret the one where the client never paid. When I was a young associate, I was assigned to do a civil commercial trial for a client who wasn't 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. Spent a significant amount of time in trial prep etc., and I win the trial. The 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). The 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."
—Anonymous
5."I do family law, and I represented a father who had lost most of his custody from heroin use and imprisonment as a result. He came to me saying he was clean and doing good and had his life together, and it checked out. He had been clean for almost nine months, not counting jail time, and he seemed sincere in wanting to resume a full relationship with his son. The other side fought viciously to keep him at extremely little custody and supervised at that, but we prevailed and got an order, restoring fairly frequent unsupervised partial custody. Not long afterward, only about three months after the case, he was back doing heroin, sold most of his furniture, and 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 my appearance at this point, so I don't know what happened after, but I imagine and hope his custody was taken away. Basically, the net result of winning that case was that the poor boy had to witness his father relapse on heroin and was exploited for money. Worst case I ever won."
6."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 totaled his car. During the trial, the arresting police officer testified that my client was clearly drunk at the accident scene and that my client was loudly blaming the accident on a jerk who stole his car, crashed it, and then fled before the cops arrived. However, according to two other witness statements tendered into evidence, it was my client’s friend (the passenger) who was screaming about the person who stole the car, not my client (the driver). The cop 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."
"At the time, the acquittal was somewhat unexpected for me (in my personal view, my client was clearly drunk and responsible for the accident, regardless of who was blaming the mystery jerk to the cops), 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 criminal case. The regret? About a month after the acquittal, my young client called me at 3 a.m. from the police station saying, 'It’s me again! The police arrested me for drunk driving again! Can you help me?' Not only did I answer no, but I instantly regretted getting the earlier acquittal. My client apparently didn’t learn any lessons..."
7."I work in medical malpractice defense. Once, I had an obstetrician/gynecologist who burned a patient during a procedure. When I met with the doctor, he lied to me throughout the representation over 16 months, saying he had no idea how it happened. There is a doctrine in law called 'res ipsa,' meaning absent some sort of negligence, this accident could not have occurred. The woman came in without a burn, and after the procedure, she left with a burn. There's no way this doctor didn't know what had happened."
"The area of the burn was where he was operating on. It wasn't until I brought up settlement, because this was not a case we could win did he say, 'Oh, maybe I do know what happened.' We ultimately settled that case, which is considered a favorable outcome, considering the potentially high monetary verdict. Sometimes, I think this doctor really ought to have lost that case and their license."
8."I wouldn't say I regret this so much as to this day it amazes me. As a first-year associate, I was given a (terrible) PI 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 he had a torn rotator cuff, which was undoubtedly not related. My job was to allege the flu shot caused the rotator cuff tear. Our ortho actually correlated the two (which is the more regrettable position), 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, just overwhelmingly made me feel like the worst stereotyped attorney, and I just hated having to walk into court on it and feel my reputation being destroyed."
9."I do juvenile work, criminal law and family law. I represented this client first when he was a juvenile charged with disorderly conduct at school and fighting; then when he became an adult, it was for things like possession of marijuana. As he got older, it became easier and easier to figure out what part of his life hasn’t gone as well as it could, and I tried to counsel him and push him to better himself. He got his GED, started going to NA (Narcotics Anonymous), started classes at a community college, and found a part-time job. On the night of his 21st birthday, he was charged with a DWI (driving while impaired). Of course, I’ll take care of that, too. About six months later, we are due in court for trial (on a Monday), and he doesn’t show up, which at this point in his life, is highly unusual. As I’m trying to figure out where he is, the court starts going over arraignments/first appearances, and then lo and behold, three people are up for murder charges."
"The prosecution starts to tell the judge what the facts/circumstances of the case are and mentions a few victims' names. Apparently, my client was at a party when these three individuals decided to allegedly do a drive-by shooting. My client suffered multiple gunshot wounds and didn’t make it to the hospital. So... by default, as you can’t prosecute a dead person; the State has to take a dismissal. I guess technically a win. Either way, it was crushing to me as I thought he had really turned his life around. (He had)."
10."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 illegal or mind-bogglingly 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. What an awful person. The ex-wife received an 'anonymous' tip and was able to get him back quickly."
—Anonymous
11."As a personal injury attorney, I've seen a few clients winning the 'blue collar lotto' or getting more money than they reasonably know how to deal with. I do my best to educate them, but my job is to try and maximize their recovery, not teach them finance. I have definitely contributed to a few drug habits."
12."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."
13."I won a summary judgment motion that my firm filed not expecting to win. We had a decent argument, but the odds were way worse than a coin flip, and judges don't like granting summary judgment because it's an extreme remedy. 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 (because the Supreme Court said the trial judge should have denied our motion). So, we are back at square one. North of $100K in legal bills, with no resolution. Maybe it'll settle, maybe it will go to trial. I'll find out in the next three to four months."
14."I worked in criminal defense and represented a guy in a DUI. He had priors, so another conviction meant time, loss of license, and problems. Long story short, he was pulled over by police after they followed him leaving a bar. At trial, I elicited admissions from the arresting officer that during the 2.5 miles that he followed him, he did not observe a single moving violation — no speeding, erratic driving, driving over the lines, blowing stop signs, or running red lights. Didn’t even 'stop suddenly' at red lights."
"Also got the DRE (Drug Recognition Expert) 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.' The jury came back in 15 minutes. The guy was extremely grateful, and his lovely family was very gracious in thanking me and our office. I felt good about the whole thing. A couple of 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 sexually assaulted his 8-year-old step-daughter. I think about that one a lot."
15."I helped represent a landlord in a lawsuit regarding discrimination in public housing based on disability. The state was representing the disabled tenant. The facts were pretty clear, the landlord discriminated on the basis of disability. Our state doesn’t have much case law regarding discrimination in housing based on disability. So, the state was really hoping to get make case law. 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 landlord. I imagine the state wanted to proceed to trial, but the tenant needed money and accepted."
"By gaining the best outcome for our client, we allowed the landlord to get off basically scot-free and deprived our state of needed case law."
16."There was a case that I saw that involved a claim with fee-shifting — meaning that if the plaintiff won, their attorneys’ fees would get paid by the defendant. The defendant pushed an aggressive legal position at trial that the judge agreed with and won, avoiding a few thousand in liability to the plaintiff and a few thousand in attorneys' fees. 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. The high court agrees with the plaintiff, reverses, and sends back to the trial court — which now enters judgment against the defendant for a few thousand in damages against the plaintiff and tens and tens of thousands of dollars in attorneys’ fees from the appeal. The defense lawyer probably regretted winning at first on that aggressive argument to the trial court."
17."I settled a personal injury case for a guy, and he was set to get about $5,000. He was in jail. I held the money for a couple of months, and when he got out, he came by to get the money without delay. The next day, the cops came around and asked if I knew him. I explained that I did. I was told he died that night of an overdose, and the only thing found on him was my card, some drugs he had not yet used, and a needle."
—Anonymous
18."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."
And finally...
19."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 — and that his employer fired him after he had been on disability leave for almost a year. 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 pissed me off."
Fellow lawyers, what's a case you regret winning and why? Feel free to share your story in the comments below.
Note: Some responses have been edited for length and/or clarity.
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