Lawyers have an obligation to uphold the law and ensure that their clients have the best representation possible. They must do their best to represent the client even if it has a lasting effect on them personally. Sometimes, lawyers will have a case that makes them believe that if they win, true justice will not prevail. These cases can have lasting negative impressions on lawyers who only want what best for everyone. Below, lawyers share the cases where they truly hoped they wouldn't win.

Change The Definition
Change The Definition

"Defended a company that attracted a bunch of its employees with a profit sharing incentive scheme.

After 5 years (when the incentives were due to be paid) they tried to change the definition of 'profit' in the employee contracts so they could argue that no incentives were payable. I was neither surprised nor unhappy when the judge told our clients they were full of it."

The Client Got What He Wanted All Right
The Client Got What He Wanted All Right

"My friend used to be a plaintiffs personal injury attorney, and he told me this story today about how he 'lost' his client some money.

The client was trying to use his kid to get money from a car accident. Didn't just take the kid to the ER, he took the kid to a chiropractor, tried to act like the kid was real hurt. (Pro tip - kids don't get the kinds of soft tissue injuries that adults and especially the elderly can get.)

So my friend does some extra negotiating, and gets most of the settlement money paid to the kid. His client doesn't realize until after the papers were signed that most of "his" money was going to sit in the courts registry and go to his kid when he turns 18. He got angry, and my friend was like, 'I thought that's what you wanted, I got a lot of money for your kids injuries.'"

Real Estate Scam
Real Estate Scam

"I worked at a civil firm and our biggest client for a while was a real estate investor who was the most unpleasant prick I've ever met.

His favorite scheme was buying 'distressed properties' (translation: unlivable pits) at foreclosure sales, selling them on credit to people who couldn't afford to purchase a house any other way, waiting for the buyer to fix the place up with their own money, and then finding an excuse to foreclose on them so he could buy the place back and sell it for more to somebody else.

As you can imagine, this is wildly illegal and got him sued by many, many people. Trying to defend this indefensible prick against the people he cheated was a nightmare, but I desperately needed the job. We dropped him as a client when he stopped paying his bills and I hope he winds up behind bars or bankrupt."

Teamwork To Lose
Teamwork To Lose

"Family lawyer here- associate so I don’t get to pick my clients yet.

I had one where both parents sucked (substance addicts). I had Mom. But didn’t want either parent to end up with custody. Division of Family and Children Services had been called but had deemed it not severe enough to warrant removing the child. So I ended up calling another lawyer and strategizing with her to represent the grandparents so they could intervene for custody. It worked, child is with grandma and doing much better! Parents are still addicts."

The Whole Office Wanted A Denial
The Whole Office Wanted A Denial

"I’m a law student but the place I worked at last summer was a civil litigation firm with one partner who did mostly criminal defense. None of the associate attorneys liked getting assignments from that partner, since none of them had really signed on to do criminal defense work.

Anyways, one associate ended up having to write an appeal for a guy who was convicted of assaulting and murdering his young child. There was a serious constitutional violation that the appeal was based on, but realistically the entire office was hoping the appeal would be denied, including the associate who got stuck writing it.

I don’t know what happened, not gonna say where it was, the associate tried his best, no one got disbarred, yes it sucked to work on it knowing the guy was guilty."

"Nice And Courteous"

"Social Security Disability attorney here. I’ve had this feeling more than once:

-Clients who lie to me (or the judge), particularly about substance use. I’ve got your medical records. I can see all your blood tests and urine tests. I can see what you’ve admitted to your doctor. If you’re not going to tell the truth—to your own lawyer—how am I supposed to help you?

-representing a guy who was a registered offender. He was in his 50s when convicted; victim was under 14. He was denied disability. He was always nice and courteous but I just despised every second in his presence."

"Took A Toll"

"My mom had this case like six years ago where she had to defend a man who killed his ex girlfriend’s one day old baby.

I remember my mom would come home every day and just cry. She’s had a lot of cases where horrible things happen to kids and she’s always been so afraid something would happen to my brother or me. It really took a toll on her."

Horrible Person
Horrible Person

"A serial killer murdered a locally famous man in 2017. This victim owned a restaurant and was very popular in the city. He was a good human being.

About 6 months after his murder a lady comes in claiming his house was hers. Back track about 20 years...the client and the victim bought a piece of property together. They are both on the title. They split up and she leaves a property that is literally falling apart. The property was close to being condemned. The victim hasn’t had contact with my client in 15 years. He did all the work on the house and paid off the mortgage.

The victims kids are suing my client for half the house. If there is a God, they would get all of it.

In short...a house she had nothing to do with, that is worth 600k might be Hers because a serial killer murdered the owner. She is a horrible person. I want to quit the firm over this case."

"Hannibal Lecter Style"

"Not a lawyer. But I use to be a Lyft driver and drove a group of lawyers to an adult club once.

One of then told me about a case he did earlier in the year. The guy was on trial for murder and assault. The dude was apparently crazy as heck and nobody doubted he was guilty. He was actually chained to a chair with a mask on. Hannibal Lecter style. His job was to try to get him off.

He said he would try his hardest to get him to walk, but prayed to whatever god was listening, that he would freaking lose.
The guy got life with no chance of parole. He was relieved, but then switched to a different law firm."

Wasn't Expecting A Win"
Wasn't Expecting A Win

"Immigration attorney - had a client sign up after having his visa cancelled as he was convicted for assaulting his ex-partner's kid.

I wasn't in a position in my firm to refuse clients because I'm a junior and senior attorneys would go nuts. We had multiple risk assessments since his offending saying he was the lowest of low risk and testimony that he wasn't assaulting kids.

I got his visa back for him. Still don't know how I feel about it. I didn't want him to lose the case per se I just wasn't expecting it to be successful."

"The Saddest Fart"

"I prosecuted two cases against a defendant for substance possession. They were slam dunks...guy got arrested by the same officer at the same location and made the same admission. It was literally the same trial. He had several priors and faced a minimum of two consecutive prison sentences of 10 years each...he faced 20 years. I hoped he would be acquitted because (a) that is a freaking insane amount of prison time for a small amount of substance, (b) he was a vet who was injured in combat, and (c) he was relatively young and had to use a colostomy bag.

My prick of a boss wouldn’t allow me to deviate from the office policy plea offer. Defendant goes to trial and is quickly found guilty. He should have testified because I wouldn’t have objected to anything. The kicker was that when the first verdict was read, he let out a long, loud fart. It was the saddest fart I’ve ever heard.

He ended up getting 10 years total bc the judge ran them concurrently. After that, I got chewed out by my office for not arguing with the judge that he had to run them consecutively."

Love At First Sight
Love At First Sight

"Represented a guy at trial who had beaten up his girlfriend pretty bad. It was a loser, and the trial was more about what the punishment should be than whether he had done it. Jury was out for way too long, and when they gave the verdict, it was Not Guilty. I was astounded. I must be some kind of great lawyer.

But no. One of the women on the jury held out, insisting he couldn't have done it in the face of overwhelming evidence of guilt. After the acquittal, we visited with the jury to get feedback about the trial. Judge, prosecutors and I wandered into the jury room and everyone's eyes were on this woman. She asked to meet my client. She had fallen in love with him at first sight from the jury box.

I told her no, I couldn't do that to her. But his name was there to be known, and I think she got in touch with the guy later. But I really hope she didn't. Guy was an animal."

"Shake Like A Girl"

"The brother of a good friend of mine is a nationalist. Skinhead, thinks immigrants and not poverty is his main problem and likes weapons and stuff. He isn't an activist, participating in violent acts etc, yet he is a total prick.

My friend calls me one day. His brother was arrested for illegal possession of weapons. He was stopped while driving for a typical substance test and the police found a... police baton in his trunk! He had bought it through dark Web and he was stupid enough to carry it in his trunk.

My friend begged me to help. I did, and I did it only for my friend, which I love very much.

The guy 99% never used it or any other weapon as well. He is just a stupid bully who likes to appear dangerous. When we met he was so scared and it was really funny watching this pile of muscles shake like a girl in fear of going to jail.

For a guy like this, I would never use any fake story or narrative to defend him. We just tried to prove that he didn't intend to use it, that he never was violent and it was just plain stupidity.

I was hoping that he was sentenced. It is a misdemeanor, so he would get no jail time, but I'd hope for a nice fine or some tens of hours of social services at least.

But the judge, for f... sake liked the honesty. He sentenced him with parole, which means if he doesn't commit any crime in the next two years, he won't go to jail and his criminal record will stay clean.

In the end, he was happy not to go to jail. But I scared him, explaining in depth what would happen if he was caught for any illegal action from now on. And I think he will behave from now on."

Stupid Witnesses
Stupid Witnesses

"Fresh out of law school I was working as a public defender. My guy was an unrepentant Driving Under the Influence who made the roads more dangerous for all of us. He got into a non-injury accident and the police took over an hour to arrive.

The prosecutors called well meaning but incredibly stupid people as witnesses. I gave my guy the best defense I could by making the witnesses look confused and at fault, and by suggesting that it was possible that my guy was so stressed out by the accident that he started drinking after the fact to calm his nerves. He didn't testify himself, and there was no way to prove he was drinking before the accident. He got off, and about a month later, I quit."

"It Was Gross"

"I represented a company when there was infighting among the partners. A few of the partners came to me with a plan to buy out another partner. However, this plan was essentially a way to scam this person. I’m not sure if they thought I wasn’t smart enough to figure it out, but when I called them out on it, they owned it and said that their plan was to dupe him into taking an offer and then scamming him.

I pushed for an amicable resolution (i.e., a fair deal), and they went along with that for a while. The partner they were trying to buy out was not willing to leave without negotiating, and my clients didn’t want to hang around. They fired me and are now with someone else. I know the attorney they went to, and I can’t imagine they’re crossing the unethical line I wouldn’t cross. The sad thing is that I really respected these folks, but they clearly did not have any respect for me or their partner. It was gross."

Surprisingly Likable
Surprisingly Likable

"Two times when I was not quite a lawyer but doing work experience/student:

1.Child assaulter in court after police found indecent images of children on his computer. Wanted him to go straight to prison just off of that.

2. I worked in my universities pro bono clinic. We received a request from a convicted child assaulter who was already serving a prison sentence to review his case file to see if he could appeal the length of the sentence on the grounds that he had been sentenced under the wrong sentencing guidelines. Conducted an interview in prison with him and my supervisor. Was one of the most surreal experiences of my life. We thankfully couldn’t assist. He was polite, and to my naive surprise at the age of 20, likeable. Took a long time for me to reconcile those feelings against what I knew he had done.

Counterbalance - work experience at a criminal firm, defendant was a British veteran who had served in Northern Ireland, became a substance addict and spiraled into a cycle of criminal behaviors, clearly was suffering from PTSD and other mental health issues. Was in court for battery and actual bodily harm and was pleading guilty. I (for reasons surpassing understanding) ended up in the interview suite alone with him. I’ll never forget how he broke down and described to me how he knew his life was out of control but couldn’t seem to stop or break the cycle, how he so desperately wished he hadn’t ended up back here and how he’d essentially watched his whole life destroyed. He was crying - I had no idea what to say or do, but I desperately hope he got the help he needed.

Those experiences combined were enough to put me off ever practicing criminal law."

"He Broke Down Crying"

"I used to do plaintiffs work in credit card debt collection cases. Yes, I was that prick.

One time we were suing a guy for $3k. He had some type of cancer of the throat and had one of his jawbones removed. He was in really bad shape.

Prior to the hearing, the guy told me he quit paying when his wife left as she couldn’t deal with his cancer. Also, his church had collected all they could to help him - $1k in cash. Also, he said he was ‘judgment-proof’, which means he’s so poor that there was no way my client would ever see any money from him (extremely common).

I called back to the office with his proposed $1k to satisfy the debt in full and my boss said, 'I don’t care about his jawbone. Tell him $2k or no deal!'

The trial was brutal. He broke down crying when I got him to admit he intentionally didn’t pay his credit card bills due to his medical bills. He was clearly broken. I pitied the guy so much but still did my job and won. We got the full $3k in our judgment.

By the way, our client was a 3rd-party debt-buyer, meaning they bought the debt for $.02/$1.00 of debt.

This means that our client was rewarded $3k + court costs + attorneys fees for something they paid $60 for and will never be able to collect on."

Try Not To Be Too Obvious
Try Not To Be Too Obvious

"Criminal lawyer in the UK. I once defended a guy who killed his own new born child because it was crying so much. Literally hurled the child against the wall.

At the time I had recently become a father too. I wanted that guy to do serious time. The jury convicted him of murder and he got a 14 year custodial sentence. I found it really hard not to celebrate."

There's Always A Catch
There's Always A Catch

"I've had to defend a hospital who didn't want to be held accountable for taking too long to admit a patient who died because of such delay. I was thrilled to see they lost, and disappointed to see how much they paid."

Too Much To Bare
Too Much To Bare

"I represented a major automotive service company that upcharged unneeded products and services to an old car that they were not designed for. The products failed- killing two people and making a third an amputee.

Pushing company policy as a defense (industry norm) and being instructed to degrade the moral character of the deceased was too much for me."

It Was An "Accident"
It Was An

"Not a lawyer but a friend is.

He was working a case against a well-known company for under cooking food and causing a family to get food poisoning.

He had told me about how this family is known to the company he works for and tries to gain money from crazy things. This time he said they had a reasonable case.

He went on to speak with the family and asked which company it was the mother responded with one company while the dad responded with a completely different company name.

My friend then went on to 'accidentally' bring this up in court."

Rot In Jail
Rot In Jail

"I was a lawyer for criminals and most of the crimes were just stuff like stealing and some other petty crimes.

But then there was this one guy who was convicted of killing his wife and 3 kids while wasted. Now all the evidence was stacked against him and he would come in to talk to me while he was so wasted what he was saying was rubbish. He was also an absolute prick and I really hope we would lose the case. He ended up getting 9 years in jail."

"It Made Me Feel Awful"

"I used to be an Insurance Defense attorney in-house for a big insurance company, and this happened to me all the time. It was usually because the facts and evidence would show that our Defendant was at fault for something, but the insurance adjuster insisted that we fight it. I would do my best to explain to the adjuster why the evidence or law was against us, usually after I’d had time to gather the evidence and take Plaintiff’s deposition so I had the full picture. But at the end of the day, I had to proceed until/unless I was instructed to settle.

Two stick out in my mind. (1) Case involved defending a driver who sped around the corner and hit kids crossing the street. I had to argue that the injuries weren’t that severe because no bones were actually broken. (2) Case involved fighting our own insured client who had been in a hit-and-run accident. It was later discovered that the other driver had been high when he ran the stop sign and plowed into the insured client. He had no insurance so the client needed us (her own insurance company) to pay for her medical bills, but I was instructed to fight her on it in every way possible (minor accident, not that hurt, bills inflated, she’s young so she’ll be fine, etc). It all made me feel awful. The good news is that I have now switched over to the Plaintiff/claimant side and I’m so much happier. I can at least use everything I learned from being insurance defense to help my clients."

IP Theft
IP Theft

"I worked at an Intellectual Property Law Firm and I was handling a Client who was legitimately trying to get away with Trademark Squatting. He would get international brands trademarked in his name and as soon as the brand tried to obtain registrations for their marks in India, or use their trademark in India, he would file a suit against them for IP theft and then later sell the trademarks to them at an exorbitant price in exchange for withdrawing the suit.

On top of actually committing IP theft, he was an entitled little prick, calling us Associates up at odd hours demanding last minute changes to drafts before filing. He created a WhatsApp Group especially so he could text the entire team with absolutely redundant queries often asking us to include completely irrelevant information about him and his various 'brand'. Because he had filed multiple suits against multiple brands, for a long time I was handling all of his trademark matters and I hated myself for being his lawyer.

Minimal Effort
Minimal Effort

"I am a defense attorney. I had a client who committed a triple homicide, and bragged to me about it when we first spoke. When I was preparing for the case, I decided that I wouldn’t try my hardest. There was a boatload of evidence, and at least six witnesses (it was a shooting at a small restaurant). He lost the case, and was sentenced the first-degree murder. He got two life sentences (with no parole)

Honestly, deep down, I’m glad he’s locked away."

"Continue To Fight"

"I’m a guardian ad litem and I’m currently advocating for a child in an abuse case (because that’s my job) even though I’m not convinced anything happened.

She has a lot of mental health issues and never disclosed to anyone until she got mad at the guy for an unrelated issue. Her story has changed over time and she won’t speak to anyone about the incident, she will only write about it very vaguely. She has no details and says the memories come in flashes and in nightmares. She also recently disclosed that she is having some trouble with her brain and they may have to do surgery to relieve the swelling.

I will continue to fight for her, but I’m honestly hoping to get it settled."

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