Lawyers have a difficult job. Yes we make fun of them and often make their lives miserable but they are just doing their jobs to the best of their abilities. They are human... contrary to popular belief. They have plenty of moments and mistakes they regret. And in hindsight they often look back at a win as a fail.

Redditor u/Mr-Ard wanted to know if any of the law professionals out there were wiling to fess up by asking.... Lawyers of reddit, what case you wish you never won?

Was I happy I won? 

Client hired IT consultants from another consulting firm. The firm basically found qualified people and rented them out, sort of like a recruiter but they get fees forever (common in IT consulting). Client eventually thought he was paying too much (even though he agreed to it), and stopped paying. He owed $200k.

In NJ, you need to be licensed as a consulting firm. If you're not, you can't sue for your unpaid bills. They sued anyway, tried to argue some loopholes. We won, client paid nothing beyond my legal fees.

Was I happy I won? Meh. Gave me a great story, great for my reputation. Doesn't feel great helping out a douchebag though. I'm an underling who had no role in being able to reject the case, so that was a little bit of a consolation at least. CarolaMckey

No Coaching....


Not a lawyer, but I became friends with one after my friend took USAA to court after they wouldn't pay a claim when their member rear ended her on her scooter after she stopped for a stop sign. Their lawyer kept talking to me to try to coach my friend on what to say, but she just wouldn't listen. He was a nice guy and wanted to help her since his client was obviously in the wrong. Unfortunately, USAA won and she was stuck with a $12k ER bill. AggravatingEducator4


I represented a man accused of murder. I was able to get him off on a technicality during his arrest but it was pretty clear he was guilty of the murder. I truly regret getting him off because he was most definitely guilty. 2stepgarage



Lifelong public defender, here. None.

I will also say that my feelings for a client are rarely impacted by what they are accused of having done. I've had accused murderers whom I enjoyed working with. I've had accused shoplifters I've wanted to strangle. aolowa

Pain in the Neck....

When I was an insurance defense attorney there was a guy who sued one of my clients after she hit his car and hurt his neck. He was legitimately hurt bad enough to where he couldn't do his job anymore. I had to defend her and I did a good job from her and her insurance company's perspective and all he got was his past medical bills. The jury should have given him a lot more than that, and I have felt bad about that for years. ipaywithlitecoin

Medical Issues.... 

I represented a foreign medical company, they have a worldwide monopoly in a treatment for a specific kind of cancer. They used to sell these treatments to hospital and other public organizations. They had a fight with buyers for the price of the treatment, they wanted to be paid way more of the price set up by the hospitals, so they decided to fake a shortage in some of the components needed and stopped producing this product worldwide, leaving a lot of patients to certain death.

After some time that they came back to produce that same product and their price demand were met. They had both criminal and civil consequences, but In the end I managed to reduce the their responsibility to just a small economic fine which was less than 0,001 per cent of the profit they made with this whole operation. Mim3sis

Looking at the Dying....

I won a case for a pharmaceutical company that was accused of selling contaminated products. My cases were all against people who had developed terminal illnesses and I fought tooth and nail to discredit the scientific experts that the plaintiffs put on the stand.

I started out losing cases and the sting of a loss lasted a day or two. The mistrials were best because we kinda "won," as in kicking the can down the road. Looking at a dying person when the jury read their verdict in my favor will never leave me.

I didn't show up at work for months, then kinda sat at my desk for a few months, then eventually quit. I'm living off my savings now (not as much as you'd think) and volunteering for organizations that need lawyers.

If I'd lost that case I would have stayed in my happy world indefinitely. I'm glad I'm out of that world but that win took its toll on my life. Cheef-Justice



Well once you've taken a case (more realistically, it was given to you) you have no choice but to do whatever you think is necessary for the best interests of your client. To do anything less open you up to a malpractice lawsuit.

Also, don't forget there are lawyers on both sides of the case with the same duty to their clients. So in the end the 'winning' side is simply the one that put forward a stronger case. shouldbhi

New Career.


The one thing this post is teaching me is that I could never be a lawyer because I have a conscience.

And I mean no offense by this. I am sorry that you folks have to live with these things. I know I am not mentally strong enough. TheGoodGovernment

In a funky country....

None of them. I want to win. I knew though that I'd have a tougher time not being emotionally engaged with family law and crime and anything else really emotive and so forged a career where it's companies and cash at stake.

Now I work in-house as a litigator for a multinational co covering disputes throughout the world. I always do make sure that if we're thinking of litigating in a funky country that the penalties aren't inhumane. No interest in someone getting executed or flogged for messing with the Company. aolllllllll

"They found me NOT guilty??"


I had a misdemeanor stalking case once. Client wanted a jury trial so we did that and I had to question the poor girl who was getting harassed by this guy. The jury came back with a 'not guilty' verdict, and my client turned to me and said incredulously, "They found me NOT guilty??" Yeah, that case. ThePrimCrow

Germany Tales... 

Right before taking my bar exam in Germany I was working in a small law firm as a law apprentice. There was one case which was given to me, because it was considered unwinable but the client insisted on pushing through. The case was about an elderly lady who sold her cat, because she was too sick to take care of her.

The buyer of the cat our client, a rather wealthy lady, took the cat to the vet right after buying it. Apparently the cat needed 2000€ worth of surgeries. She hired us to collect those 2000 from the old lady. She was really an unpleasant woman to say at least.

She acted without even the slightest bit of remorse or empathy. She knew exactly in what situation the old lady was, because she was the one who informed us about it. Nevertheless we won the case pretty quick even though our client didn't have a leg to stand on. CrystalDexter

big city in America....

I used to prosecute neglect cases for Child Protection Services. After a few high profile cases where young kids ended up dead at the hands of family members, CPS starting asking us to file on pretty much everybody (I understand why, but I wish they would have stood up to the bad press instead of allowing it to dictate who they brought to court).

From that point on, I would say about half my cases, even though a cause of action existed, I felt guilty for winning. folicfoil

Copyright Issues...

We took a copyright case to trial twice, and then an appeal, and won every time. The case was on contingency (the client doesn't pay unless you win). We have spent years trying to collect the judgment from the defendant so we can get paid (we have a judgment for our own fees that is close to $1 million), throwing good money after bad.

The Defendant hid his assets very effectively (put all hard assets into LLCs, got paid hundreds of thousands a year in cash and services to avoid banks, etc.). He died of covid19 on Friday, and was likely savvy enough to avoid probate.

All of this is a gross oversimplification, but the TL;DR is we won a case three times, and have never been paid a cent because the loser was very shady and died, so we will likely get nothing for the client or ourselves. 3choplex

We won.


Was a labor lawyer for some time and we had a no-exception policy against using the company credit card for personal expenses. Everyone knows you get fired for it because they beat it into you with frequent training, make you sign stuff, etc. We fired a guy who was a few months from retirement, and his union filed for arbitration.

Arbitration is kind of a joke and any labor lawyer will tell you that no arbitrator would uphold that termination even if the guy wasn't near retirement. We won. Due to the way the pension worked, the fact he left before he reached 55 led to a massive pension discount, like hundreds of thousands of dollars.

Oh, by the way his offense was fulling up his car with gas using company card because he had left his personal card somewhere and was going to run out of gas. (On the other side of the coin I had many employees do insane things like hide and sleep at work for 40 hours, lead to a 30,000 gallon gasoline spill, fighting, death threats, etc who all got their jobs back through arbitration). LenoreHalperin


Seeing lots of armchair lawyers in here, but I can tell you the cases we often wish we lost: the ones where clients don't pay their damn bills. Actually getting paid is one of the most stressful parts of practicing. dustydeceiver

At a Loss....

Worked for a large law firm. We 'won' freedom for a suspected terrorist who probably did commit a very serious atrocity but politics got in the way of convicting him.

Sorry cannot say which case this was. sundialsoft

I'm used to do divorces....

I'm used to do divorces, mostly. I'm not cut out for that work but it's the job I could get out of law school. A guy came in for a divorce and seemed, by all accounts, really nice. He claimed that they had $50k in cash in their safe and that his wife had taken it out when she left the house. His ex wife never worked so seemed reasonable she would take the money to help pay bills, start over, etc. 6 months in though, when we were finalizing property, his true colors started to show. Refusing to let her have the toaster, arguing over giving her anything even though she hadn't worked their entire 15 year marriage, telling her she could have half of the expensive plants SHE tended to only if she came and got them herself without help.

For reference, these plants were in a green house and some weighed upwards of 100lbs each (she probably weighed 100lbs herself; extremely meek woman in her 60s). The other lawyer and I finally get everything settled except the $50k. My client says she took it, ex wife says she did initially but then put it back on the advice of her attorney. So we go to trial just on this $50k. I cross examine her elderly parents, treat them as hostile, really go all out. Up against a veteran attorney who had been doing this for 30 plus years while I was BRAND NEW, I had to show my worth.

In the end, the judge ended up declaring that the $50k was "lost money." No one, technically, wins. 1 hour later my client waltzes into the office and pays his $15k bill all in $100 bills. I just stared silently at the money while he smiled widely at me, thanked me for helping him and then left. I quit practicing law entirely 3 months later. I still think about his ex wife (who honestly seemed sweet and lovely) and hope she's okay. aworldofnonsense

Insurance Issues....  

one of our cases was trying to get the lowest possible amount for a guy who while doing his job in a stationary car was hit from behind at full speed (his car was off the road the other driver was impaired) and his car was slammed into the 18 wheeler he was helping. He is forever handicapped and in a home and our job was to get him way less than he deserved... I didn't want to work insurance defense anymore after that one. quint1993



I always thought it would be cool to be a lawyer until I had to pay 63K in attorney fees over the course of 2 years for custody of my daughter. Now I'm not complaining so much about the money, more so about watching her attorney try to turn a turd into a piece of gold, no matter how irrefutable the evidence against her was.

I wouldn't be able to live with myself or sleep at night defending on cases like that where I would potentially be trying to return children to drugs, abuse, neglect and etc. mienkio


Do you have something to confess to George? Text "Secrets" or ":zipper_mouth_face:" to +1 (310) 299-9390 to talk to him about it.

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