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Lawyers Confess Which Cases They Actually Regret Winning

I sold my soul because of the law....

Lawyers Confess Which Cases They Actually Regret Winning

Lawyers are not the devil. In fact we need people of the law to make sure we're all getting a fair shake. Lawyers take an oath to uphold the constitution and law by any means necessary. Everyone is entitled to competent representation. No matter what. And often that representation may cause some issues. But the law is the law. Fair or not. Let's look further into how we fix that.

Redditor u/ahtemsah wanted all the lawyers reading to share some life lessons.... we're listening to your pain... you were asked.... [Serious] lawyers, what's a case you regretted winning?



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 screwed, years of treatment. Internal issues, psych issues - really just messed 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 crappy situation. dieabetic

Family Law Heartbreak. 

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. DemonFirebrand



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. lessworkiskey

You're Out! 

Eviction law - basically every other case. Even the morons. It's not rewarding to put people out on the curb. Ever.BeattieLaw


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. unbelievablepeople

back at square one.....


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.



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. EssenceOfEspresso

Define "Win!"

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. WholeMilkStandard

Plot Twist....


I convicted the father of murdering his wife and years later found out he lied when he confessed to cover for his teenage son who actually been the one who killed her. In the meanwhile the son committed suicide father was content to serve his time in prison. curiousidaho

(Personal Protective Order)

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 2 months later the victim ended up getting put into the hospital by the client (he beat her). That one still bothers him. davonoches

I'm Out.

Guy lost his wife and children in a car accident. He wanted to exercise to get his emotions and mental health back in check. Doctor wrote him recommendations for exercise equipment (ball, chin up bar, nothing crazy) and he submitted the expenses for same to his insurer.

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. ChipSmash

Climb the Pole.


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. ezkwyer

By Default...

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. phitheta219

"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 drug habits. Uncivil_Law

No Lessons 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 totaled 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 ahole 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 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 asshole 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.


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.

The Burn. 

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. mclarenf1boi

Criminal defense is a hard business.

Had this happen to me twice. Got my client out on bail only to thereafter have him up and killed. First time, he was in building supposedly selling, got chased by the police and a struggle ensued where he was shot point blank in the head. Mother told me that it was my fault that he was killed and that i was working with the DA and the police.

Second time, a young man no more then 16 gets released while waiting 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 killed in a drug Related robbery. Mother blamed me and said that the devil was working through me that we were all demons.

Criminal defense is a hard business. Armtoe

"stop suddenly"


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 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." 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 assaulted his 8 year old step-daughter.

Think about that one a lot. MakeBelieveNotWar

Fee Shifting?

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. dotajoedotajoe

Gross Dad.

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. mintrawr


Any other barristers want to unload?