30 Cases That Still Haunt The Lawyers Who Regret Winning Them

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.

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.

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