Lawyers Were Asked Which Cases They Regret Winning, 40 Shared Heartbreaking Stories

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.


Did a simple eviction for non payment of rent just last month. Super easy. Won the eviction but found out after the hearing that she didn’t pay because her cancer treatments we eating up all of her income.

Felt awful but worked out a deal after the fact so she kept the apartment.

Image credits: sailingawayagain


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 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. F*****g a*****e. The ex wife received an “anonymous” tip and was able to get him back quickly.

Image credits: anon


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.

Image credits: unbelievablepeople


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.

Image credits: Awesomegen01


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.

Image credits: LawyerLou


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. 

Image credits: mintrawr


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.

Image credits: charmcharmcharm


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.

Image credits: chamtrain1


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.

Image credits: Ultracrepidarian_S


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.

Image credits: spicy_mountain


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.

Image credits: just-wanna-vent


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.

Image credits: mrfixit420


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.

Image credits: GeraldoLucia


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.

Image credits: aj613


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 they 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 d**k.

Image credits: Hiredgun77


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.

Image credits: anon


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.

Image credits: DemonFirebrand


Prosecuted a murder case. Twenty one 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 a*s. The older guy sends some nudes of the ex while he’s getting drunk at a bar, so the kid says something smart a*s in response. Older guy comes to the kid’s house to fight him. The kid shoots him once, and the older guy dies. 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. S**t’s going to haunt me until I die. No doubt about it. Started thinking about other work the moment the verdict came back.

Image credits: Quijanoth


I’m a work comp attorney. Now represent injured people, but used to work on other side insurance defense.

There was an applicant with a serious injury. Fell off a ladder, busted back with fusion, shoulder f****d, years of treatment. Internal issues, psych issues – really just f****d up. 50%+ permanent disability. We were 5 years in and finally getting to settlement time. If we bought out his future medical, settlement pretty far into 6 figures. This guy was the sole provider for wife and 2 kids.

Then we found out he had a aggressive brain cancer. Expected only couple years to live, at best.

Thus, we wouldn’t buy out future medical anymore. Still got permanent disability for $60k-ish… but can’t give medical buyout based on 25+ year life expectancy anymore.

I felt terrible for the guy and his family. Me and the adjuster tried to get insurance to agree to some sort of amount like 5 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 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 s****y situation.

Image credits: dieabetic


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.

Image credits: anon


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.

Image credits: mclarenf1boi


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

Image credits: phitheta219


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 arresting police officer testified that my client was clearly drunk at the accident scene, and that my client was loudly blaming the accident on the f*****g a*****e 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 a*****e 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 a*****e 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 am 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, I instantly regretted getting the earlier acquittal. My client apparently didn’t learn any lessons…

Image credits: Horrified_Witness


Divorce case, represented wife who was pissed because husband left her for another (younger, thinner) woman.

Wife reported that their young daughter made a comment about something that could be interpreted as molestation by her father (i.e. the husband). The only conceivable corroboration about the comment would have come from the daughter’s testimony, but 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 criminal prosecution of the father, because there was no other evidence of molestation. But the wife pushed for sole custody and a requirement that the father would only get supervised visitation for the next year or so. 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.

Image credits: Sir_Clicks_a_Lot


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.

Image credits: zer0sumgames


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.

Image credits: EssenceOfEspresso


Got late to the party, but this story still makes me sad and angry. Not me, but my ex-boss. Civil matters.

The firm represented a large construction company here in my country. They built and sold 30 houses (in Spanish; en un Fraccionamiento).

There is a lot of corruption going on here in Mexico, and in this case, the company paid off a large amount to not follow construction regulations and save some money.

Turns out, some years (I believe it was 2 years) after all the houses were sold, there was a massive water malfunction which led to flooding, and 85% of the houses collapsed or were inhabitable, the construction company being at fault.

The people obviously sued for the prices of their homes and damages of furniture etc., but they could no longer because the legal figure they could use (wrongful construction) had already prescribed (passed the time to legally make a claim).

My ex boss is a very gentle soul and a great guy. He always remembers that case as the worst one, and says everyone to reject similar ones because the guilt is way too consuming.

People lost their houses, their furniture, their electronics.., and most had mortgage or similar debts in order to pay for them. Breaks my heart.


I’ve had a few. Debt collection cases, evictions are up there. Especially this time of year. I have been appointed on some child abuse/neglect cases where I kept out evidence that was pretty damning.

I had a client who I got released on probation on a drug charge. He was killed the next day in a drug deal gone wrong.

You learn to distance yourself from the case emotionally and do your job or you don’t last long.


I worked in Criminal Law my first summer of Law School. My first case was defending a Large 6’2” teenage gang member who stabbed a rival gang member in the temple with a pencil with deadly results.

I was put in charge of the motion drafting and research under a supervising attorney. I also had several conversations with this young man but he was remarkably well-spoken so I never felt like he was an actual killer (even though he admittedly was one).

I remember working really hard in the library for hours looking for helpful case law. It felt great in the moment to help your client in any way possible and put up the best defense.

Ultimately, they conditionally discharged him, which is Family Court (since he was a juvenile) parlance for 1 year probation, I remember my emotions immediately shifting from relief to guilt/fear. I questioned the entire practice area that could allow a killer to walk the streets because of good legal work and I ultimately decided it was not for me. No judgment to any Criminal Attorneys, just not for me.

Now I’m a happy-ish Real Estate Attorney; and by happy-ish I mean kill me now.


I’ve posted about this before. I defended a death case, representing the insurance company. A man had a brain injury due to a car accident, and died six months later. His family sued my client.

I’ve never seen a lazier effort on behalf of a Plaintiff. The Plaintiff 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 actual medical evidence they had come up with to link the death 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 o/c 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 didn’t show up because his dog was sick. No joke. As I predicted, all of her evidence was thrown out. The family was crying. I won but I didn’t feel great about it.

The Judge was appalled. I’m sure the firm was sued for legal malpractice. The young associate was gone within weeks.

Image credits: KevWill


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

Image credits: orm518


I’m a clerk for an appellate judge so my winning and losing only really takes place when I try to convince the judge (and the rest of the panel) to take a certain view on a case. I recently “lost” and a guy I definitely think committed the sex crime he’s alleged of is going to walk. I have to write the opinion which makes it sting a lot worse too.

Image credits: vtzan


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.

Image credits: ezkwyer


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.


Recently I won a case where my client had made a very bad decision causing a terrible accident and I truly believed that the plaintiff was hurt in the accident and deserved compensation. But she was an awful witness—plus her whole life was basically a huge mess which made it really hard for her attorney to pinpoint for the jury exactly what issues were related to the accident. The jury gave her a judgment that was half the amount of the medical bills, and that was completely offset by no-fault insurance payments. So she walked away from trial with $0.

The flip side is that we made her a decent offer prior to trial, so she could have had thousands of dollars had she settled.


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.


It’s worth noting that (embarrassingly) opposing counsel brought it to our attention after they spoke to some of his former coworkers who recalled him bragging about being in the league.


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.


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. 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’s 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. 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 attorneys’ fees from the appeal. The defense lawyer probably regretted winning at first on that aggressive argument to the trial court.


The one where the client never paid.

[edit: Clarification/explanation; 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. Spend a significant amount of time in trial prep., etc. I win the trial. Client never pays (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]


As a personal injury attorney, I’ve seen a few clients win 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.

Leave a Comment

Your email address will not be published. Required fields are marked *

Advertise with Us!

Download the latest TAAT Global Investor Kit

Download the latest TAAT Global Investor Kit