Article created by: Gabija Saveiskyte
Lawyers have a reputation of being ruthless and cutthroat, doing anything necessary to win a case. Even if they may not agree with everything their client has done ethically, everyone is entitled to legal counsel, and we all want to have a bulldog in our corner when defending ourselves.
Sometimes, however, even lawyers have regrets about how things have gone down in the courtroom. One curious Reddit user recently asked attorneys to share stories of cases they wish they hadn’t won, and hundreds weighed in with heartbreaking memories. Below, you’ll find the most powerful responses, so be sure to upvote any that hit home for you.
Felt awful but worked out a deal after the fact so she kept the apartment.
My mother was a prosecutor for thirtysome years. The worst case that still haunts her was of this fifteen year old girl who was a fat Asian girl who got pregnant. So she hid the pregnancy the entire time from her very abusive parents, gave birth in her bedroom without them finding out, then hid the baby in the closet and it died from suffocation. Clearly the teen was horrifically in the wrong, but she was so beaten down and abused and terrified of her parents my mom wished she could have charged them instead and let the teen have a normal life.
As a former employment lawyer I regret defending a company in a law suit in which the employee had an acident and lost her left leg, had the left side of her body covered in burn scars because of the companies fault.
The case was more or less like this.
This lady worked at a toll on a highway, whenever she needed to go to the toilet she’d have to close the toll, change the sign lights to red so no-one would go through that toll.
Unfortunately due to lack of maintenance, the lights did not change and when the lady was crossing the road a car ran her over, dragged her 10 meters.
After defending this case I realised I did not want that in my life, I wasn’t meant to be a lawyer so I dropped everything and quit the week after.
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.
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.
One of my cases I can remember well is one about a man who was accused of a sexual crime toward a women. His story kept changing and we all knew he had done it but he wouldn’t admit to it so we went on with it. Somehow he had evidence on the women and ended up winning the case. To this day it scares me to know he’s out in the world probably doing it again.
I recently saved an insurance company $2,000 on a settlement with an injured person. Not as exciting as the rest, but it’s one of those quietly sad moments where you question why you even went to law school in the first place.
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 for was for simple 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, he started going to NA, he 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. Of course I’ll take care of that too.
About 6 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 low 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)
EDIT: Wow, this really blew up. Thanks for all the positive comments. And the bling.
Also, since some people asked for clarification or were confused.
1: I truly believe he was on the right path forward.
2: GED = High School Equivalency Diploma
3: NA = Narcotics Anonymous
4: DWI = Driving while impaired
I successfully got a kid kicked out of a very good school district because the single mom didn’t live in the Distirct and wanted her daughter out of the shut district she was in. We proved it by videotaping the kid leaving another house outside the district on 7 different occasions.
I was a brand new attorney and had to take the case.
Still feel bad about that.
A divorce and the wife (who I was representing) wanted to give away custody of her 2 children to her husband who clearly didnt want them for her 3 million dollar yacht. Personally I would have her keep both the 3 mil and her children. I still regret winning that case for her.
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 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 afterwards, only about three months after the case, he was back doing heroin, sold most of his furniture, and for me the most soul-crushing 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 afterwards, 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.
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, slumlord 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 tenants 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 needed money and accepted.
By gaining the best outcome for our client, we allowed the slumlord to get off basically scot-free and deprived our state of needed case law.
I have handled my fair share of domestic abuse cases….about 90% of which end with dismissals. I never like winning them, but almost always do.
Settled a personal injury case for a guy and he was set to get about $5000. He was in jail. 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 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.
Late post so this will probably get buried. This is another family law story, using a throwaway because some of my colleagues use Reddit.
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 seemed to have a fairly high paying job, it seemed 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, still, about 50k in backpay, but she was content with 15k, which was less than this guy made in a month. I did regret the ‘win’ though, 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 wounded ego.
Edit: I should also note that though they had two kids together, both were in their 20s by the time I was hired, and custody had never been an issue at all, even for the one who had been a minor when they’d separated.
I helped a guy successfully sue his ex-fiancée for the engagement ring after the relationship ended due to “third-party interference” on his part. It was wild–and wildly depressing.
I work in medical malpractice defense. Once I had a 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.
Woman came in without a burn, and after the procedure, the woman 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 potential high monetary verdict. Sometimes I think this doctor really ought to have lost that case and their license.
Little late to the party, but I’ve got one I still think about a lot. Worked in criminal defense, represented a guy in a DUI. He had priors, so another conviction meant time, loss of license, 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 he followed him for, he did not observe a single moving violation – no speeding, erratic driving, driving over the lines, blowing stop signs, running red lights. Didn’t even “stop suddenly” at red lights. 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. Guy was extremely grateful, and his lovely family was very gracious in thanking me and our office. Feel good about the whole thing.
Couple months later I’m in county to meet with a client, and I see him in one of the pods. Find out sometime after the trial he violently sexually assaulted his 8 year old step-daughter.
Think about that one a lot.
Edit: The comments have helped. Thanks.
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 just hated having to walk into court on it and feel my reputation being destroyed.
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+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.
The one I particular 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 under the influence 8 times, violated home incarceration countless times, been caught with controlled substances a few times, and stabbed two people on home incarceration. My boss at the time was the master of getting people off for DUI’s so she had only been convicted of a DUI third and 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 kill someone someday. But I’ll be damned if she isn’t the luckiest woman alive in getting away with DUIs.
My client made a lot of promises to his staff and never had planed to keep them. Was sued, won. I hated every second of the case.
work for a lawyer, most ill say is we won a guy a fat fat stack of cash and he gambled it all away within 2 weeks. My bosses jaw hit the floor when he heard that.
I won a summary judgment motion, that my firm filed not expecting to win. We had a decent argument, but odds were way worse than a coin flip and judges don’t like granting summary judgment because it’s an extreme remedy.
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 3-4 months.
ETA: clarified my parenthetical
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