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Lawyers Share the Most Morally Challenging Cases They Ever Worked On

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Being a lawyer is tough. Some lawyers defend individuals who have done morally reprehensible things, while others help powerful insurance companies, corporations, and other entities take advantage of less powerful people. “Legal” doesn’t always equal “moral,” as all lawyers know very well.

Current and former lawyers took to AskReddit to share the most morally challenging case they’ve ever worked on, and these stories aren’t for the faint of heart.

1. Arguing over $5000.

“During my days of insurance defense, I spent one lovely afternoon bickering with counsel for a co-defendant over who would be responsible for paying the $5000 that was keeping us from settling. We did this while on-site at the plaintiff’s home for a deposition. Plaintiff was hit by a semi-truck (i.e., the truck hit his actual body) on the interstate, and while it managed not to kill him, it tore off an arm and a leg, and shattered most of everything else. He was almost entirely immobile, confined to a power chair that he could barely operate, and confided to us that if he had function in his remaining hand, he’d shoot himself.

“Oh, the $5000? It was based on an estimate to renovate his bathroom so that he could actually use it. He’d been pissing and shitting in a bedpan in the living room.

“I felt like a complete fuck sitting in front of him and arguing about such an insignificant sum.”

2. Getting a fuel company off scot-free.

“Not my case, but at a previous firm, a partner sent out a firm-wide email congratulating his team on a great win. It detailed how their win meant that our client, Giant Fossil Fuel Company, wasn’t liable for damage to the environment caused by leaks in their pipes. Instead, the tax payers would be covering the cost. The partner went on to say something to the effect of ‘this saves our client $x billion a year in environmental cleanup and pipe maintenance.’

“For some reason, even though it wasn’t my case, that one has always stuck with me.”

3. Defending a murderer.

“Had a case where a guy shot and killed a security guard that slapped him across the face for selling drugs near a store.

I knew the guy had done it.

It was close to midnight, the crime scene had poor lighting and the shooter wore a hoodie. Only eye witness that showed up for the trial had told the police at the time of the crime that the suspect was black. The defendant wasn’t caucasian but wasn’t black either. That, IMO, was the argument that won the jury over. Defendant found not guilty.

He thanks me while in tears. His mother and grandmother bring me cake and a thank you note afterwards.

Less than a year later I’m watching the news and they’re reporting a crime where a crew held up three families hostage while robbing their apartments. They beat up the janitor very bad. They tied the families up and locked them in one of the apartment’s bathroom while threatening to thow a grenade inside if any of them decided to wisen up.

For a brief second one of the robbers looks right into an elevator camera before spray-painting it. Close-up on the guys face.

I think you can imagine whose face I was looking at.”

4. Defending a child rapist.

“Not me but my brother is a criminal defense attorney. He worked as a contracted public defender for a few years after starting his own business to get some guaranteed income while building his client base. The catch with these contracts is you’re not able to refuse clients.

He had to defend a guy that had repeatedly raped his toddler daughter while the mom watched.

When I asked him about how he got through it he said, “when I get to a point where the crime is so heinous that I can’t empathize with my client, I switch my frame of thought from ‘how will I get this guy reduced or no time?’ to ‘how can I ensure this guy won’t have a chance at a mistrial.’

So essentially, he copes by making sure that everyone from the police, to the jailors, to the prosecution team are 100% on the up and up so that when this guy gets found to be guilty, there’s no way he’ll get set free on a technicality.”

5. Hearing an abuser in front of his victim.

“Did a bail hearing back in my second year of practice as duty counsel, think public defender type role. The guy had trapped his girlfriend in the cab of his pickup. Twisted one arm up behind her back to her shoulder and broke it. Then did the other side.

I had to run the bail hearing for him. While she and her family were sitting in the front row of the court. She had both arms in casts and in slings. Thankfully, his surety (the person posting his bail) melted down on the stand and we had to adjourn. By the time he was up for bail again he’d retained private counsel. Who put the same surety up on the stand even after I warned him not to. In front of the same Justice.

Upside? He got detained.”

6. An alcoholic mom.

“Family law attorney here. I’ve done plenty of divorces and custody dispute cases, that most stuff doesn’t get to me. It’s only when the kids are put in a bad situations between one or both of the parents being some type of addicts that really gets to me.

One that was especially hard for me was a divorce where I represented dad. Mom was a raging alcoholic that would bring random guys home many nights from the bar while the dad was working. I saw video and heard phones calls from their little boy calling the dad at work at like 2AM because he was tired, but couldn’t go to sleep because mom was playing loud music and had ‘friends’ over still partying.

I was on the right side of that one, but seeing and hearing that stuff with the little boy really got to me.”

7. Unwittingly defending a guilty friend.

“My friend’s dad is an attorney. He started out in criminal defense, and lucked out on one of his first cases. A friend he’d known for years wife was horribly murdered while he was away, dismembered with an axe. Her body had been found by a fluke, and there was a tiny bit of circumstantial evidence pointing to the husband. He was an upstanding citizen, the two had never fought, it was a silly case. The lawyer got the husband acquitted, and while they were having celebratory drinks, the husband admitted he’d actually done it.

“My friend’s dad walked out of the bar and switched to corporate law.”

8. Picking the wrong parent for custody.

“I represented a mom in a custody case. Both parents fighting for primary. Mom was admittedly a mess and suffering from some mental health issues. Dad took the kid and didn’t bring them back for a few months in violation of the order. I got the kid back. Then met with mom and kid and realized kid was doing way better with dad and should be with him. Tried to reason with mom, she didn’t listen. Ultimately the child protection office got involved and child was placed with dad. I last saw mom many years ago and she was still not in a super healthy place and child was still with dad. So best ending happened and not because of me.”

9. Any child sexual assault cases.

“I’ve only worked as a legal intern not a lawyer, and I cannot speak in specifics for obvious reasons, but I’ve dealt with about eight child sexual assault cases at this point. I helped prosecute most of those, but played a role in the defense on a couple. I can tell you, either which way you’re working the case, it’s tough. Nothing is more terrifying than reading a young victim’s description of being abused at the hands of a trusted family member.”

10. When justice isn’t practical.

“Legal, smart, and moral are very different terms which don’t necessarily go together in legal work. Actions can definitely be all three. I think the toughest decisions are moral, legal, but not ‘smart’.

The most morally challenging case is the one where a client has been wronged, but circumstances make holding someone to account too difficult or expensive to be accomplished. Telling a client ‘you have been hurt by someone who did something illegal, but you can’t do anything about it. Sorry’ really sucks.

Bringing a medical malpractice action can be really expensive. Some states require you hire a medical expert to present certain evidence. Some states cap the amount of damages you can recover. I’ve seen some egregious behavior shrugged off because the (probably) at fault party knows that most people can’t afford to bring the case.

Every case is a big deal to individual clients. Losing, or getting a bad outcome, is never fun. But telling a client that someone is going to skate because it’s too expensive feels morally worse.

11. When the consequences don’t match the crime.

“I could handle the murder trials, drug charges and real estate squabbling no problem. It was watching poor people get ground up over minor offenses or simple mistakes, little things that would haunt them for the rest of their lives.

One particular case stood out to me. There was shooting and a crowd had gathered around the body. A detective was asking people in the crowd if they’d seen anything. Our defendant said ‘yes!’ when he hadn’t seen anything really, but he just wanted to help. He was a simple-minded person, but never formally diagnosed with anything largely due to the lack of services in my town and the fact that he dropped out of school early. When I met him it was clear that he was a sweet person who really liked people, but was dealing with a low IQ and some reasoning issues.

The detective separated our defendant from the crowd and started questioning him. After a few minutes it was clear that the defendant was just giving answers that he thought the detective would want to hear. He really wanted to make the detective happy. Instead of just dismissing the guy, the detective arrested him for giving false information. He had a few minor thefts on his record (again he had reasoning issues), so he was really looking at serious jail time because he talked to the police (again, this dude just liked talking to people and didn’t know better). He had no diagnosis or health records to back up any claim of mental deficiencies and anything resembling that would cost money he didn’t have or time in a state mental facility. He lived with a relative who was equally broke.

His lawyer was contemplating a guilty plea because he’d lied directly to a police officer and admitted it. I left before the case got resolved, but it’s the one I still think about. This guy was largely harmless and was likely going to spend at least some time in serious jail, where the outcome would likely have been very bad for him. The thing that stuck with me was how unnecessary it all was. It was suffering for literally no purpose. Putting him in jail was not going to magically give that guy better cognitive skills other than making him distrust people.”

Like I said…yikes.