14 People Recall the “OMG… WAIT!?” Moment They Knew a Court Case Was Won

If you’ve spent any time around actual courts and lawyers, you probably realize things aren’t as exciting as they are in the movies. That said, there can be moments when a case clicks at just the right second – and those times are pretty dramatic and fun.

These 14 people have stories from cases they’ve been involved in, or tried, and they’re all good enough to put into a television script if you ask me.

Let’s dig into this craziness!

14. Social media will get ya.

When I found a video on Facebook of the plaintiff squatting 300 pounds the month before his deposition.

That was a good one.

Oh he was saying he couldn’t work and had back injuries after a minor car accident.

13. Straight despicable.

I represented an elderly indian couple, who didn’t speak English very well and owned a rental property. They had a tenant at the time who had not paid rent in over six months. They had tried to evict her on their own, but when they got to court, the tenant produced some hand-written notes which they had given her the year prior thanking her for payment (but they failed to date the notes.) Of course, the tenant added recent dates herself.

The tenant also produced a partial certified check receipt, but most of it was illegible. Anyway, because of their poor english, they had difficulty understand the questions and giving intelligent answers, so they lost the initial case. They hired me to help address all of the various lies that the tenant was putting forth.

Anyway, we refiled. I had my clients pull the banking records, so we could show the date that the certified check was actually deposited into their account.

The plan was simple, let the tenant make the same arguments and then present the banking statements showing the deposit date. My clients also found a photo copy of one of their notes, but it was undated (unlike the copy the tenant presented the last time).

Well, when the judge finally understood that the things the tenant had presented occurred the year before, his cheeks turned bright red and he asked the tenant “what year did you make this payment?” The tenant started saying something like she couldn’t be exactly sure when… and the Judge cut her off again in a very loud voice “what year?!”

Needless to say the clients got their eviction granted.

Bonus: When the tenant arrived at court I watched as she got out of her car, walked to the back and pulled out a wheelchair and proceeded to stay in that wheelchair until the case was over. Once the Judge left the courtroom, she folded-up the wheelchair and carried it to her car mumbling that she “hates f###ing lawyers.” Anyway, that was a very satisfying day.

12. Realtors are your friend.

Tried to sell my home myself and the buyers wanted a term period for land contract before getting their own mortgage. I agreed to one year, had a simple contract drawn up and after we both signed it everything seemed fine. Within thirty days the present me with their own legally drawn up land contract that was pages long to “protect their investment”.

About page three it very clearly stated that “if for any reason the home burns down, purchaser will receive all insurance proceeds”. First, I still had a mortgage and the proceeds would legally go to pay that off. Second, that’s a pretty targeted thing to say. Not lawyers terms of the house being destroyed, and it’s surrounded by woods and waterways, just if it burnt down.

Page four stated that this would remain a land contract until my mortgage was paid in full, so they’d never buy outright. I returned it to them with a letter stating those two things were never happening and I wasn’t signing.

They stopped paying so I began eviction. Six months later the lawyer I hired was an idiot and I’m sitting down with their lawyer myself. He brings out the contract they’d tried giving me and began talking about their iron clad case due to the agreement.

I asked him to show me my signature…. the look on his face when he realized it wasn’t there. After we talked it turned out he knew them and wrote the contract without the burn the house down stipulation (seems they added it) and under the belief it was a long term land contract.

Not only did I “win” I’m pretty sure they lost a lawyer friend

11. That’s a lot of trouble with no case.

My client was accused of brutally murdering a dog.

Cop testified that there was no testing of the blood, no body ever found, and admitted it could have, in fact, run away.

The eye witness said she could see the killing down the hallway from the dining room.

Cop testified there was no hallway and the dining room was on a different level of the house than the killing supposedly took place.

Then the person who was leading the lynch mob against my client around town for the last year testified that she had been in the apartment between the two visits by the cop to evaluate the scene.

No body, a compromised crime scene, witness who couldn’t see anything, and admission that there was no proof the dog was dead.

Closing argument lasted 3 seconds: “Your honour, I’m asking for an acquittal”.

10. Show me the money.

Bought a hurricane door from a contractor that was found through our states hurricane readiness website. He took 5k and after about 3 weeks of “car” or “scheduling” issues, finally just ghosted us. Took him and his company to court. The him AND his company part is important.

Finally court day shows up and I’m fairly young and an optimistic so I figure I don’t need a lawyer, plus the local news station took my story and came out to interview me to do a bit on it. I figure it is a fairly obvious case, easy win. I put on my best (only) $99 suit and head downtown. Dude doesn’t show but instead sent his company’s office manager.

We get settled in with the arbiter (first thing I was wrong about, “oh shit, not court court with a judge and shit?”) and the office manager starts in that they deny my claims and infact are counter suing me for canceling the contract. I start to sweat, “like oh shit, they’re going after me? What happens if they believe them? I’m going to be out 5k AND have to pay them more? FML!”.

The arbiter listens to her and then asks me to tell my side. I told him, plus showed documentation of what I had did and when. Arbiter dude looks at her and says “he has enough to prove you wrong buy even if he didn’t, because your boss Michael blahblah couldn’t even be bothered to show up when he himself was specifically named in the suit, I’m ruling in the plaintiff’s favor.” Cue me trying not to happy dance or look to smug before I got out of that room.

Side note, just because you win a judgment against someone, that doesn’t mean you will get paid.

You still owe me $5k Michael!!

9. Not the smartest bulb.

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.

8. Wait, what?

“My client has been keeping her son away from the father because the father has a new child. She is concerned that her son will act violently towards the new child and she could be held liable.”

Judge: “That’s not even a defense!”

7. He just couldn’t hold on.

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*cking p*ssy” (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.

6. It’s not always a good time for a pun.

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.

he 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.

5. That’s unfortunate.

I trapped a defendant pretty badly one time. He testified in a depo 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 2 months after the wreck. Case settled for policy limits a week later

4. That’s just silly.

Not a lawyer, but was working as a paralegal for a law firm. We were defending a claim which had run into tens of thousands of pounds against our client (a holiday home), by a woman who had tripped over a speed bump while walking back to her caravan, and damaged her knee. The fall was genuine. The question was whose fault this was. She claimed it was the holiday home’s fault because she hadn’t seen the speed bump due to low lighting, poor marking etc. The claim had (outrageously) gone to months, and made it to court.

Going through the various questions to her, when our barrister asked how she knew the speed bump was poorly marked (or something similar). Her response “Well, I remember thinking how it wasn’t well marked when I was walking up to it”. Needless to say it was a short day in court after that point.

3. That must have been satisfying.

Years ago I had to do something at a strip mall in a bad part of town, took me about 20 minutes and then I found that my car had been towed. Ubered to the tow yard. Giant sign says ‘cash only’. Had to call another Uber, drive to the ATM and back, and pay them $300-some bucks. Got a shitty hand-written receipt that, believe it or not, was itemized.

Went home, googled, found that they violated the law in three separate ways: towed illegally; illegally refused to accept credit cards; and had multiple charges that the law called ‘unreasonable’ like dolly fees and load / unload fees.

Took them to small claims court.

The judge began by asking the tow yard owner about his relationship with the property owner and how the decision was made to tow my car.

“Oh,” the slimy tow truck dude answered, “my cousin works there, if he says tow, I tow. It’s a hundred percent legal!”

The judge’s eyebrows begin to rise.

“But,” the dude continued, “BUT what I detest the most your honor is this ASSHOLE claiming I don’t take credit cards. I’m a businessman! I take credit cards all the time! He’s a low life that does not have any credit cards, that’s why he wanted to pay cash!”

I was having a “HOLD IT” overload, and the judge saw me smiling and hopping in my seat and patting my manila folder of receipts.

“Do you actually not have any credit or debit cards?” the judge asked me.

I pulled out my wallet and showed him, and then I pulled out a timestamped photo of the “CASH ONLY” sign I took the day of, and another one I took the morning of the hearing.

The guy mumbled something like “OK you got me there” and then had nothing but “Huh, I didn’t know that” when the judge asked him about the legality of each unreasonable itemized charge.

Anyway, each violation pays double the total tow charge, and since there were three, that’s how I made $1,800 on a $300 investment.

2. Embezzlement much?

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.

1. Good luck meets hard work.

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.

I’m so intimidated by courts and lawyers; I’ll probably never have one of these stories unless something bad happens.

If you’ve got a good one to share, the comments are open!