February 4, 2020 | Scott Mazza

Lawyers Share The Cases They Regret Winning

Deadlines, client demands, long hours, changing laws and the uncertainty of being paid or not make the practice of law one of the most stressful jobs out there. Sure, the client may actually be the one who has the most to lose or gain from a trial, but the outcome can take a serious toll on the lawyer, too—especially when that outcome benefits the worst and most selfish people. The law isn't always fair. Below, lawyers share the cases they regret winning.

Don't forget to check the comment section below the article for more interesting stories!

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#1 Fighting for a Dog

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. The ex-wife received an "anonymous" tip and was able to get him back quickly.

#2 Winning the Blue-Collar Lotto

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 bad habits.

#3 Not Getting Paid

The one where the client never paid.


#4 Trading Custody for Furniture

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.



#5 The Passing of a Client

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 simple things like possession. 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 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 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 didn’t make it to the hospital. So... by default, as you can’t prosecute a lifeless person; the State has to take a dismissal. I guess technically a win.


#6 A Bad Mom

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 her 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." She then explains the ''problem'' was that her boyfriend abused the girl and after that, she had the gall to ask if we pick up HIS defence. One of the things that made me quit to government work.


#7 A Sincere Man

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 he 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.


#8 Money, Money, Money

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' 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 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.


#9 Insurance Fight

One 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 (ball, chin-up bar, nothing crazy) and he submitted the expenses for the same to his insurer. The client (insurer/adjuster) wanted this fought tooth and nail because exercise equipment was only covered for physical rehab and he was not physically injured. I do not practice in this area anymore.



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#10 Bail Gone Wrong

I got my client out on bail and he was ended. He was in a building supposedly selling and got chased by the police and a struggle ensued where he was hurt in the head. His mother told me that it was my fault that he was ended and that I was working with the DA and the police.



#11 Criminal Defense

A young man no more than 16 gets released while awaiting trial on robbery. One of the conditions of release was that he maintain a curfew. That very night he breaks curfew goes over to somebody else’s house and was ended in a robbery. The mother blamed me and said that evil was working through me that we were all demons. Criminal defense is a hard business.


#12 Family Law

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 percent or more 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.

#13 $100k in Legal Bills

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. 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 or four months.


#14 Reputation Destroyer

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.


#15 A Bad Doctor

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, 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. It wasn't until I brought up a 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.


#16 Spoiled Brat

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.



#17 Bad News

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. He fell off a ladder and busted his back with fusion. His shoulder was messed and needed years of treatment. Internal issues, psych issues—really just messed up. Fifty percent permanent disability. We were five years in and finally getting to settlement time. If we bought out his future medical, a settlement would be pretty far into six figures. This guy was the sole provider for a wife and two kids.

Then we found out he had aggressive brain cancer. He was expected only a couple of 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 plus year life expectancy anymore.

I felt terrible for the guy and his family. I and the adjuster tried to get insurance to agree to some sort of amount like a five-year buyout, 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 plus years he decided to take $0 in fees. I have so much respect for that attorney turning down $10,000 in fees to help his client in a very terrible situation.


#18 Exploited Son

I do family law and I represented a father who had lost most of his custody from substance 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 afterward, only about three months after the case, he was back doing illicit substances, 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 afterward, 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 get exploited for money. Worst case I ever won.


#19 Good Man Turns Out Bad

Worked in criminal defense, represented a guy in a DUI. He had priors, so another convocation 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.” 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. 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. Find out sometime after the trial he assaulted his eight-year-old step-daughter. I think about that one a lot.


#20 White Aryan Resistance

I helped a man regain the visitation of his child after a year or so in jail. I thought I was a great humanitarian. Oh, the hubris that comes from being a baby attorney! As we were talking after court waiting for his ride, he showed me his prison tattoo: giant letters on his torso that spelled WAR: White Aryan Resistance. I’m a blue-eyed blonde, so I guess he thought I was down with the cause. I went home and threw up.


#21 Upset Wins

If you win a case you're not supposed to win under the law, it means that the judge or the other attorney screwed up, and it's difficult to feel bad about that. It also means that the decision likely will be appealed, which makes it hard to get excited about an "upset win."


#22 Spinal Injury

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, falls down the stairs. C6 ASIA B incomplete spinal injury—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 legal 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.



#23 Blew the Money on Illicit Substances

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 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 passed away that night and the only thing found on him was my card.


#24 Repeated DUIs

The one 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 under the influence eight 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. But I’ll be damned if she isn’t the luckiest woman alive in getting away with DUIs.


#25 Promise Breaker

My client made a lot of promises to his staff and never had planned to keep them. Was sued and won. I hated every second of the case.

#26 Hidden Money

I represented this construction worker in a divorce. The wife stayed at home with the kids and had no money. Through the 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.


#27 Family Law Custody Battles

Family law custody battle. They are never good and are almost always about money and vengeance.


I'm a paralegal, not a lawyer. I worked very closely on a case where the client had violently abused 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.


#29 Disability Accommodation Case

I handle employment cases. We took a disability accommodation case against a regional retail company. To be clear, we were right: our client was not being given a pretty easy accommodation. Normally, demand letters don’t have any real effect. We have stopped sending them to streamline the process and have just started filing with the EEOC or the courts directly. That’s SOP for us.

In this case, we followed SOP and filed with the EEOC. The company got in touch with us immediately, expressing horror and regret. The whole thing was one poorly trained manager acting out. While that’s common, companies usually try to cover for the manager and often make things worse. This one did not. They immediately sent him to be retrained, offered the exact accommodation requested, and paid all lost wages and fees, with some extra for emotional distress. The client happily accepted and went back to work.

After seeing the company’s great response, I felt bad for taking them to the EEOC. Not bad enough to start sending time-wasting demand letters again, but if I ever see them on the other side, I’ll make an exception.


#30 Another View

I have been a licensed attorney for 9 years and I am fortunate to say that I have not had any cases that fit that bill. As others have mentioned, most civil cases settle and most criminal cases get plea-bargained. It is subjective in those situations what you call a "win" or a "loss."


#31 Eviction Cases

Eviction law. Basically every other case. Even the worst people. It's not rewarding to put people out on the curb. Ever.

#32 Client Will Walk

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 an opinion which makes it sting a lot worse too.

#33 Domestics

I have handled my fair share of domestic abuse cases....about 90 percent of which end with dismissals. I never like winning them, but almost always do.

#34 Not God's Work

Worked at a public defenders office, helped a criminal get a sweetheart plea deal. I quit three months later. All the lawyers in the PD’s office thought they were doing god’s work and congratulated me on doing a good job.


#35 Personal Protective Orders

Not my case, but a former associate of mine won a PPO motion hearing (Personal Protective Order) where he represented the person who the order would have been put against (not the victim). The victim's request to put a PPO on his client was denied, and like two months later the victim ended up getting put into the hospital by the client. That one still bothers him.


#36 Got Stiffed

I poured a ton of effort (and emotion) into a case and got a great result—only to get stiffed. No it's cool, I made sure they didn't foreclose on the family farm, but just ignore my bills.


#37 Didn't Pay Up

I won a million-dollar work injury claim. I completely blanked the claimant on behalf of the employer and their insurer, then withstood the appeal. I regret it not because the claimant had a legit claim (he didn't, he was full of BS) and not because I liked opposing counsel (I don't, he's the biggest idiot in town). I regret it because my ridiculous insurance company client only paid about a third of my very modest bill. Screw those guys.


#38 Had to Pay Extra

We settled a case while the jury was out. We were the defendant, so we were potentially on the hook for some amount of money if the jury found us liable. While they were deliberating, we agreed to pay something. The jury came back, found us not liable at all. So we won and still had to pay the agreed-to amount.


#39 Slumlord Got Off Scot-Free

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 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 needed the 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.


#40 Legal Malpractice

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.


#41 Will Never Know

Divorce case. I represented the wife who was upset because her husband left her for another (younger, thinner) woman. The wife reported that their young daughter made a comment about something that could be interpreted poorly. 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. 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.


#42 Money Does Horrible Things to People

We settled a case for several million dollars for a girl whose father was ended. 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. The DAY she turned 18, her 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.


#43 A Kiss on the Forehead

As a former prosecutor, I tried a case where a niece (heavily by and through her mom) pressed criminal charges for assault on a female for her uncle kissing her on the forehead. Mom saw nothing but wanted to testify to present statistics, which were inadmissible and not relevant in our case. I wouldn’t put her on the stand and she almost got thrown out of the courtroom for making a sign out of napkins saying “ITS MY RIGHT TO TESTIFY."

The story was the uncle owned the house and would have to abandon it to them if he was deported. Technically an unwanted physical touching is an assault, so we won the case. Fortunately, the judge stayed judgment so I believe he was allowed to stay in the country.


#44 Future May Have Been Different

This is a strange one. I had a client where the Crown was seeking three to four months in jail. The judge for some reason takes sympathy on this guy with a bad record and gives him a fine. Serious charge but the facts were not particularly egregious and there was no minimum sentence. Did my submissions make a difference? Perhaps. A month or two later, I find out he died accidentally. If he had gone to jail, he might still be alive.

#45 Bankrupted a Guy

I once bankrupted a poor bloke who had lost his business through a natural disaster and then had two massive strokes. His life consisted of dribbling in a wheelchair. Yes, he borrowed money from the bank (my client) and couldn't pay it back but at some point, even banks need some humanity. I'm not normally one for feeling sympathy for delinquent debtors but this one was just piling into a bloke who had really suffered extreme misfortune.


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