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, lawyer win a case but feel that true justice hasn't prevailed. These cases can have lasting negative impressions on lawyers who only want what best for everyone. Below, lawyers share when they truly regretted winning a case.

Death Penalty
Death Penalty

"I was a third year law student in a clinic.

I came into law school with a very clear moral compass. I knew what I wanted to do (criminal defense) and I had very strong feelings about the death penalty. I thought there was never a situation that warranted it.

Cut to me working in my schools death penalty clinic. The way the clinic worked was that you'd typically be assigned 1-2 clients, review their case, visit them, and do research at the discretion of the supervising attorneys.

I had 1 client, and his case will haunt me for the rest of my life.

Goes in for life after a really brutal assault on a teenager during a burglary. Proceeds to move to more and more secure facilities after numerous guard stabbings and an escape attempt.

But that wasn't what got him the death penalty. See, while my guy was in Supermax, he managed to slip his cuffs, beat a guard to death with a metal bar, and throw his battered corpse down the stairs.

All of this is on video. There's no question he did it. So the jury deliberates for like a day before they give him the long goodbye.

By the time I get the case, it's about reviewing his eligibility for the death penalty. So, I dig into his case file for the testimony that appeared at trial and there's all this stuff about huge problems with his cognitive ability and like his actual brain structure.

With the supervising lawyer's okay, I do a little independent research, consolidate all the different testimony, and map it onto a brain. The conclusion I come to is pretty simple.

This guy literally has less than half a brain.

Through a combination of substance use, abuse, and birth defects, roughly half of my clients brain just is not present anymore in any meaningful way. Including all the centers that regulate hormone production, fight or flight response, and threat assessment.

I find a bunch of medical reports where people with just some of these conditions get severe behavior imbalances, and in at least 1 case psychotic episodes.

Basically, I help establish that this guy has the kind of diminished capacity that makes him ineligible for the death penalty under Atkins. If he's successful on an Atkins claim then he is structurally ineligible for the death penalty.

Do I feel good about helping to probably save this guys life? Heck no. Because it means he's going to be in a Supermax forever and he's already shown that he can kill people in a Supermax.

If he doesn't get the death penalty he'll still be in prison for life and I can almost guarantee that he will injure or kill another guard during that time, probably multiple ones.

However, if he's put to death we're executing someone who really isn't meaningfully responsible for their crimes because most of their brain is gone. He never had the option to make the right decision, or make any decision, because of his incredibly extensive brain damage.

It's out of my hands now, but they are appealing so it's going to go before the court eventually.

I drank, a lot, that semester and I'll never do death penalty work again."

Anonymous Tip
Anonymous Tip

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

Fortunately, there's the other side to family law too. I've had couples who genuinely cared about the other persons well-being and wanted me to make sure they were provided for. I've had clients who let their partner keep the pets even though it killed them, but they knew how much they meant to the opposing party. There's good and bad in all of us. We choose which we want to be."

Gave A Child For Some Furniture
Gave A Child For Some Furniture

"I 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."

Crying On The Curb
Crying On The Curb

"I 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."

Technically A Win
Technically A Win

"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 molly.

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 got caught driving under the influence. Of course, I 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 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 he had really started to turn his life around."

A "Problem"

"A woman wanted custody of her daughter.

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 explains the 'problem' was that her boyfriend assaulted the girl and after that she had the gall to ask we pick up HIS defense.

One of the things that made me quit to government work.

As far as I know (I did not follow any appeal), in the criminal sphere the guy was convicted, the mother was not considered as someone with active participation in the crime, but did fail her parental duty which resulted in minor repercussions as far the criminal sphere go.

That said, it was used to revert custody in the civil sphere. It's pretty obvious from the custody process that the dad left the city with the daughter too.

This is how much I know. I understand it's pretty shameful, but the whole thing even now makes me feel like garbage. Every single way I've thought of offering compensation to those people would feel like cheap bull used to make me feel better instead of improving their situation.

It's been almost 10 years, so the daughter is a young adult now."

Brought To Tears
Brought To Tears

"When I did medical malpractice defense work, I won a motion for summary judgment against plaintiff's family and estate of the deceased daughter. A family brought their 9-year-old girl to the hospital because she was very ill. In the end, the daughter died in the hospital with ruptured appendix. The doctor (who was not at hospital at the time) kept calling in (because it was middle of the night) checking her vital signs He never came to hospital because he believed, wrongly (disputed by plaintiff and defendant experts), that she did not need surgery. 

Over 24 hours later, she was eventually transferred to a different hospital where the doctor immediately performed surgery taking out appendix, she died of septic shock. Plaintiff's expert stated it was clear that she needed appendix taken out, and if seen by a physician in timely manner, a routine surgery to remove appendix would have saved her life. If the plaintiffs had a better expert, the case would have gone to trial and they would have most likely won.

For a full background, the girl had severe abdominal pain which her pediatrician believed was the flu. A day later, the abdominal pain was even worse. The family took her to back to the pediatrician who examined her again and advised that he believed that she had appendicitis. The family took her to the emergency room with the chief complaint of abdominal pain and fever for approximately 48 hours. The PGY (resident) examined her and documented that she appeared to be showing signs of appendicitis. The PGY advised the surgeon was at another facility performing surgery and he would be in contact with the surgeon. They ordered a CAT scan that did not come out clearly. The blood worked showed abnormally high white blood cell count, which could be a sign of cancer. The issue was whether the white blood cell count was high because of possible cancer or because of the appendix and whether immediate surgery was necessary. 

Based upon the blood work and unclear CAT Scan, the surgeon never came to the hospital to examine her but ordered more tests. The girl 'coded,' was immediately transferred via ambulance to another hospital where the surgery was performed. However, it was too late and she died. I basically tore their expert apart in a deposition and the case was over. I actually cried after, and eyes still get watery just thinking about it."

Fought Tooth And Nail
Fought Tooth And Nail

"A 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."

Lesson Not Learned
Lesson Not Learned

"In one of my first cases after passing the bar exam, a young man retained me on a driving under the influence charge. No one was hurt, but he totaled his car.

During trial, the arresting police officer testified that my client was clearly inebriated at the accident scene, and that my client was loudly blaming the accident on a different man 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 the different man 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 inebriated and responsible for the accident, regardless of who was blaming the mystery man to the cops), but I was happy my young client got off, no one was hurt, and lessons were learned. 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 driving under the influence 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."

Is He To Blame?
Is He To Blame?

"I had this happen to me twice. I 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. His 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 than 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 an illegal substance related robbery. His mother blamed me and said that the devil was working through me that we were all demons.

Criminal defense is a hard business."

Luckiest Woman Alive
Luckiest Woman Alive

"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 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 driving under the influence cases, so she had only been convicted of driving under the influence 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. She the luckiest woman alive in getting away with all her stuff."

Blue Collar Lotto
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 illegal substance habits."

Seemed Like A Good Guy
Seemed Like A Good Guy

"I worked in criminal defense, represented a guy in a driving under the influence case. 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. I 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. The guy was extremely grateful, and his lovely family was very gracious in thanking me and our office. I 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. I find out sometime after the trial he violently assaulted his 8-year-old step-daughter.

I think about that one a lot."

He Would Rather Be Homeless
He Would Rather Be Homeless

"After law school I had to turn down a criminal defense job offer because my wife got a better offer somewhere else. So basically, I followed her along and was desperate to find something. After three months of fruitless efforts, I would take just about any job that required a JD, whereas literally the only thing I ever wanted to do was criminal defense.

Three months after moving, I got an interview for a 'real estate litigation' job. They hired me the next day, looking back that was probably red flag number one. First day on the job they taught me how to foreclose on a claim of lien. These are two things I had never heard of before. Turns out, it is totally brainless work if you have the right forms. It's basically just cutting and pasting new addresses and amounts owed. So anyways, it took me about two months to realize this (when I had my first set of hearings) but literally my sole purpose at the firm (which represented over 100 Home Owners Associations) was to take people's houses away for not paying their Home Owner's Association dues. 

After my first set of foreclosures, I actually slipped into a pretty legitimate depression. I was getting paid peanuts to drive nearly an hour to work every day to do work I despised on behalf of people I literally could not pretend to care about. The straw on the camels back was when I started signing the foreclosures and realized I was THAT GUY. Ya know? I understand someone has to do the work I guess - there certainly is a lot of money to be made - but it was not for me. I did that job for three months, came home one Friday, and told my wife I'd rather be homeless than go back on Monday.

By some stroke of luck, I started a stellar criminal defense job within two weeks and all the heartache has 100% been worth it. I've won a lot of cases (you have to redefine winning and losing when doing criminal defense because sometimes even a particularly juicy plea is a win in my opinion) and never once felt bad about it. For example, I got a guy's plea deal cut from 60 years to 15 years for a string of robberies where the interrogations and confessions were overwhelmingly unconstitutional - like, the interrogations were textbook how not to do an interrogation (Missouri v. Seibert) - and stuff like that. Never lost sleep over someone not going to jail.

So yeah, every case where I took someone's house away (probably two dozen times) for not paying HOA fees (generally $4,000 or less) was the worst case I ever won. Forget HOAs."

Winning Put The Victim In Danger
Winning Put The Victim In Danger

"Not my case, but a former associate of mine won a Personal Protective Order (PPO) motion hearing 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."

Wounded Ego
Wounded Ego

"During the summer of 2018, I got work regarding what seemed, from the client's description, a pretty drawn out and messy divorce case. The husband was my client, and he made it seem, very adamantly, that his soon to be ex-wife was after his every penny. Given he seemed to have a fairly high paying job, it seemed like a pretty common type of case, the city I work in has many instances of this, it has a high cost of living and a lot of well-paid working professionals in the private industry. He was a very well-spoken, amicable guy in his late 50s, and truly seemed like he'd been taken by surprise and betrayed by his soon to be ex-wife.

When I actually got to the case, however, I was basically floored.

His wife was a working professional as well, worked in government, they'd been married for over twenty years and had two kids together, and a paid off house. Before taxes, he made almost three times what she did, not counting his stock options, and yet she'd contributed equally to their mortgage on every home they'd owned over the course of the marriage. By all accounts, despite a vast difference in income, she'd carried her weight, raised two kids, and worked full time during the entirety of the marriage. I live and work in Canada, she could have easily raked him over the coals in the divorce if it had gone to court.

Instead, it seemed like she'd done everything she possibly could to not have him subjected to that. This divorce had been ongoing for five years before he hired me, and it was basically him looking a gift horse in the mouth over and over, a constant renegotiation on the contract they'd both signed initially, with him skimping on alimony and then debating on lesser terms. He was basically given an inch and tried to take a mile, dragging it out for so long that per divorce law it had to go to court. I almost suspect he did so as a way to try to drag her through the mud, though he may have genuinely been that delusional.

I consider it a win only because his ex-wife was adamant about only wanting what was somewhat fair, and for it to be over because of the strain it was having on the family. Per the contract he owed her, still, about 50k in back pay, but she was content with 15k, which was less than this guy made in a month. I did regret the 'win' though, she seemed like a very nice woman with the patience of a saint, while almost all of his anger towards her seemed to come from wounded ego."

Lazy Plaintiff
Lazy Plaintiff

"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 my client 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."

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