The legal field is like a vast, deep blue sea full of complex problems that require even more elaborate solutions. In short, not everyone was born to be in it. The long answer is, read those volumes upon volumes of law books and you’ll find out.
But there are few things more entertaining than having the legal pros share their experience in the big court game. One Reddit user decided to curb everyone’s curiosity and pose the question “Lawyers of Reddit, what was your ‘Hold It!’ moment where you knew you would win?” on r/AskReddit.
The question got 74.9k upvotes and 10.6k comments with people from the legal field sharing their incredible trial, defense, and prosecution stories that all led to the moment of cracking the case. So get your seat closer, sit back, and let’s see what lawyers had to say.
#1
Not as a lawyer, but a defendant. I was a concierge and named in a lawsuit against the building by an unlicensed realtor who was barred from entry after headbutting me while he was wearing a bike helmet. He was representing himself in court.
He cross examines me over how I had barred him from entry and had some preamble about the vendetta I had against him. Then asked me to repeat what I said when I asked him to leave the building.
I responded, “I’m sorry, was that before or after you hit me?”
He immediately answered, “After I hit you.” Took him a minute but his face fell pretty far after he caught on to what he just admitted.
Case dismissed.
Image source: GoodChadAndUgly
#2
Very abbreviated – I was prosecuting a convenience store owner for luring a young girl, who regularly came into the store, back to a part of the store to grope/fondle and kiss her (child enticement). It was the only section of the store without surveillance camera coverage. They were in the back room for about two minutes and seventeen seconds, per the timestamp on the videos. Of the many arguments the defense put on, one was there was no way there was enough time for anything to happen. In my rebuttal on closing, I asked the jury to imagine what could happen in the room in that amount of time, and I asked them to all close their eyes while I timed out 2 minutes and 17 seconds on my watch, in silence. After about 60 seconds two of the jurors started crying. Knew it was going to be guilty right then.
Image source: Badwolf84
#3
My friend was defending a guy who was asleep in the backseat of his car while intoxicated and a NYS Trooper arrested him. On the stand, the trooper testified that he visually saw ‘the key in the ignition.’ My friend gave him like three chances to walk it back. ‘Are you sure, trooper, that you actually saw the key in the ignition?’ He said yes. And then my buddy dropped the hammer, ‘You are aware that my client drives a Toyota Prius?
Image source: dramboxf
#4
My brother went to court to gain some custody rights of his daughter. Ex-wife says he shouldn’t be allowed to be alone with the daughter cuz he looks at porn. The judge, who happened to be a woman, laughed and said, “honey, if every man who looked at porn wasn’t allowed to see their children then there would be no child with a daddy in this world”.
Image source: heavenleemother
#5
Not a lawyer, but I’m currently in a custody battle. Mother is saying I can’t be trusted because I’ve been refusing to take our child to the therapist. The therapist testified I couldn’t bring our child in because therapy must have both parents’ consent, and mother has retracted consent.
Image source: Latexfrog
#6
I’m not a lawyer, but I took my old landlord to court when I was in college. They stole my security deposit over bulls**t: They claimed I “trashed” the place, not knowing that I took pictures and video when I moved in and out. Their “evidence” was a VHS quality recording of going through a perfectly clean apartment in better condition than it was when I moved in, but then they opened up the top of the stove and found a single piece of elbow macaroni under it, holding it up triumphantly. That was the crux of their “defense”, the judge was not amused and I got all my money back plus my lawyer fees and the filing fee. She then fought against her own lawyer to avoid paying him. As**ole. Edit: Any time you move into a place, take pictures, take video, make notes about any damage. When you move out, do the same thing along with noting any repairs you made. Pretty hard to argue against solid evidence. Protect yourself.
Image source: FartsWithAnAccent
#7
Man I’m always too late but I’ve got a good one. When I was interning at the criminal court for a judge I observed a pre-trial hearing for a murder case. The defendant allegedly murdered his grandmother because she wouldn’t give him money, then stuffed her in a closet and called a hooker for sex in the bed right next to the closet. Horrifying stuff.
During the hearing the defendant’s lawyer, prosecutor, and judge went through some typical procedures, then the judge asked the defendant if he had anything to add. The defendant smugly said yes, actually, I don’t think I’m mentally fit to stand trial according to article x under the criminal procedure.
The judge let him finish, looked him dead in the eye, and said: “The fact that you just told me this shows you’re perfectly fit to stand trial.”
Image source: immalilpig
#8
Not a lawyer but got robbed at gun point in my home. Long story short, he would have gone to prison anyway but the kicker is that the shoes he wore to court were the same shoes he stole from my house. Judge asked if I wanted them back. I said yes. Judge made him take them off in court and walk back in socks. Donated the shoes, it was more about the principle.
Image source: Biscuit-ontheside
#9
Obligatory, not mine but my Moms story. She was fighting for custody on behalf of the father, trying to prove that the kids were living in subpar conditions with their drug addict mother in spite of the ample child support provided. It was a tough case because courts are so hesitant to pull kids away from their moms. Then the mom burst out that she had been feeding the kids cat food as proof that she wouldn’t let them starve. Needless to say, the judge didn’t take that as a good reason for the kids to stay with their Mom.
Image source: Keeliekins, Carol VanHook
#10
I was an attorney for an insurance company defending a lawsuit where the plaintiffs were two girls who claimed they were irreparably harmed and their lives would never be the same because severe back injuries kept them from being active. They forgot to set their Instagram accounts to private and the accounts were full of pictures of them riding jet skis, dancing, and pictures of them at the gym. The underage drinking pictures were just icing on the cake.
Image source: Zdarnel1
#11
At a termination of parental rights proceeding:
State: Ma’am, when was the last time you used illegal substances?
Witness/bio mother: I used meth this morning before I came to court
She is no longer a legal parent to that child.
Image source: elephantsonparody, wp paarz
#12
I had a ton of these when I used to do Family Law. Off the top of my head: my client’s husband was alleging she had been high and nude in public. As I’m crossing him I get him to admit that she was in fact changing out of her bathing suit at the beach and covered by a towel at all times. He says: “well, she was naked…under the towel,” I come back with: “just like you’re naked under your clothes right now?” Even the judge chuckled.
Image source: Iamtherainking77
#13
A thief robbed someone’s houses in the winter in Colorado, and all the police had to do was follow the footsteps back to his house where he was hanging out with the stolen items and a small amount of drugs and a sh**ty handgun. Idiot.
Image source: Schmliza, Miles Bannan
#14
Parent termination case I was prosecuting. Dad went on how he has changed his life around and worked the AA program. Asked him what step he was on, and he proudly proclaimed 3. Asked him what step three is, he had no idea. Then asked him step two was. Again, no idea.
Parental rights terminated.
Image source: aulstinwithanl
#15
Not exactly a “knew you would win” moment, but I got a hidden shout out from a federal judge in a ruling that I consider to be one of the high points of my career. Here’s what happened. Before a hearing for an emergency injunction against USDA, I was watching the hearing before mine (a trademark infringement case). At the end of that hearing, the judge accidentally used a pun, and could not stop laughing. She was literally crying. I decided at that moment I was going to intentionally use a pun in my hearing. I did—I accused USDA of engaging in a “shell game” by illegally diverting some federal funds to an egg industry trade group. The judge called me on it, but laughed heartily. My client won (the judge threatened to put the Secretary of Agriculture in jail). A major newspaper reporting on the case said the judge “winced” at my puns but agreed with my arguments. False! When the written ruling was issued, the last sentence said that an injunction was issued against USDA’s use of the funds for “any plans they may be hatching”. Undeniable shout out.
Image source: timshel4971
#16
I knew the cops beat up my client and framed him. They described a knife in his possession that “caused them to fear for their safety.” Oddly, they never seized it. We won the criminal case and filed a civil rights case. While deposing one, he described the knife in detail. No more than three minutes later, he slipped up and claimed his partner told him my guy had a knife, but he never saw it himself.
I told him, “that’s not what you just said,” and saw him panic. His lawyer panicked too and asked to see me outside. When we got in the hallway, I withdrew my settlement demand, and the case settled for a substantially larger amount within 45 minutes.
Image source: TerribleLawGuy, Scott Feldstein
#17
We had some huge issues with a landlord (trying to enter without letting us know beforehand, not answering to fix issues, very aggressive when talking with us) when he decided to sell the place.
He didn’t check with us about the visits and just showed up randomly with potential buyers. We told him to get lost, he eventually left but called us the same evening to threaten us. We sent emails to remind him of our rights as tenants and he answered by threatening us some more, IN AN EMAIL.
We eventually end up in small issues court (not from the US, don’t know the name) and he fabricates a story about how we are terrible tenants and we try to discourage buyers.
We just showed the judge the emails as well as the open complaint to the police we filled a few days earlier, the judge couldn’t believe it and gave him a formal warning, gave us 3 free months of rent.
In the end the guy just used a real estate company to sell the place, all went smoothly and we still live there with lovely landlords that aren’t completely bonkers
Image source: BlackZiggy
#18
My client was riding his motorcycle on a relatively calm street when this guy exited his garage, without looking, and run over him. In deposition, the guy brought a witness that was with him on the passenger seat. The whole time, the witness maintained that my client was driving too fast and that there was no time to brake the car. I asked him the same question a few times in different ways, making him tell the story again. In the fourth telling, he, already a bit frustrated, let it slip: “- Look, I’ve already told you. We were exiting the garage and, as soon as I lifted up from getting my cellphone on the car’s carpet-” “- Wait. So you didn’t even see the crash?” There was no coming back from that.
Image source: Cincosirenitas
#19
My mom hit a guy on a bike with her car in a parking lot. She claimed he hit her (she also wanted to counter sue the cyclist for scaring her) in her deposition she started every sentence with “when I hit him…”
Image source: jujuonthebeat255
#20
“Your honor, I have screenshots.”
Image source: lizzetter
#21
I trapped a defendant pretty badly one time. He testified in a deposition that he had a green arrow for his left turn, and that my client ran the red. Unfortunately for him, the additional turn lane arrow was installed two months after the wreck.
Image source: Lawschoolishell
#22
Not a lawyer, but we had no evidence that the woman who slammed into my stopped car going 85mph was drunk…until she indignantly admitted it on tape in her deposition.
She busted into my deposition and demanded she go first because I was a “lying bitch”. She excitedly told my lawyer that the police report was wrong because it said she was coming from the movie theatre when she was actually coming from her friends bar.
“Did you have anything to drink at your friends bar?” “Of course.” “How many drinks” “I dunno, they just keep my glass full.” “Did you take any medicine that day?” “Methodone and low blood pressure medicine.” “I see.”
The cops had refused to breathalyzer her at the scene because her husband was a firefighter that they knew personally. They told her to go home, sober up, and go to the hospital later. I heard the whole thing but had no proof until she handed it to me. They settled same day.
Image source: cagetheblackbird
#23
When I compared the scanned copy of the deed provided by the other side’s lawyers to the original my client eventually got around to providing.
The scanned copy provided by the other side had a witness signature. The original did not.
Image source: WolfeCreation
#24
I was reviewing the transcript of an interview with a child. The child made incriminating statements against my client. At one point, when discussing the allegations, the child used an odd word, but I didn’t think much of it.
A few days later, I was watching a video of the child interacting with their grandmother (who hates my client) from about a week before that interview. The grandmother used the exact same odd word in the exact context the child later used it. At that moment, it became clear that child had been coached. It was the first real “ah ha!” moment of my career.
Image source: ltl1109
#25
They said, ‘This document doesn’t state our company’s name, so we are not involved in the settlement.’ I said, ‘Line 4 specifically lists the company as the defendant, and then the company is referenced to in lines 13, 27, and 33.’ I swear, if you read the documents, you’re a better lawyer than 90% of the ones out there.
Image source: ullric
#26
I’m a trial lawyer. I have a ton of these.
My favorite was probably a DUI where the cop was in a BWW with my client watching a fight. Like, the cop was standing at the bar in full uniform, then when my client walked by him to leave, followed him out.
Client was only actually going to his car to grab his phone charger because he was going home with the bartender (like, he hadn’t even closed his tab yet). Cop arrested him and charged him with DUI for opening his car door, then fabricated this story for his report about how client got in car, turned it on, and began to pull out of the space to leave the parking lot. He also denied being inside the BWW – on the stand, under oath, to my face.
Surprise! I talked to the bartender at BWW and got the security tape. It very clearly (like surprisingly good quality, don’t try to steal from a BWW btw) showed cop standing at the bar, watching my client walk out the front door, then follow him 30 seconds later. Parking lot cam also showed client barely touched the door handle before cop stopped him.
Image source: ikilledinosaurs
#27
Not my case but my husband handled a paternity case pro se. His ex was trying to take basically full custody of their son and only give him visitation two days a month. Her reasoning was that he wasn’t involved, didn’t go to doctor appointments, didn’t take the kid to school, etc. My husband asked her, “When was the last time you told me about his doctor appointment?” She thought for a second and said “Never.” He asked “Would you have let me take him to school if I had asked?” Again she thought for a second and said “No.” Needless to say they got 50/50 time sharing with joint custody.
Image source: lilligant_valor
#28
Not a lawyer but I played one in small claims court. My lease had an exit clause that said if I fronted two months’ rent, they would work to lease my place and return anything unused. I checked with the office ahead of time, they ensured me there was a waiting list, so I gave them the two months and moved. They never returned a dime. I talked to the new tenant and confirmed they moved in a week later.
In court, the judge was commenting on how he didn’t see anything explicitly saying they would return any unused rent, even though that intent was stated to me a few times. Dumbo from the leasing office piped in with “your honor, in almost every case we can return some money, but in this case we didn’t have a tenant in the two months after he left.”
So she gave the case back to me and I presented the affidavit from the new tenant confirming the move in date. Judge awarded me double what they owed. Turns out leasing office dumbos 1 and 2 thought they could lie to me and “return” my excess rent money to themselves.
Image source: GiltLorn
#29
At a restraining order trial it was essentially my client’s word versus his, regarding a sexual assault. He did a good job dressing up and acting very appropriate during most of his testimony. But then he was asked a series of open-ended questions and he said something to the effect that, “She kept coming up on me with that f**king pussy” (allegedly during a lecture) and as soon as he said it a look came on his face and the judge’s face and everyone knew the ruse of respectable young gentleman had failed. I won.
Image source: BorderThug
#30
Some guy was accused of something — I cannot remember what — but the judge let him free because there wasn’t enough evidence he had done it. Guy said, ‘Thank you, judge, I’ll never do it again.’
Image source: Belgian_friet
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