Top 10 Craziest Roommate Cases on Judge Judy

The slippery defendants, Oscar and Eduardo, subleased a bedroom to the plaintiff in a three-bedroom apartment. Well, in reality, they subleased a living room for him to sleep in. But they still charged him. What already sounds like an unfair situation got worse when the defendants’ relatives moved into the same living room they rented to the plaintiff. Their roommate didn’t just sit down and take this, and they think he’s in the wrong. Their entitlement speaks volumes. Judge Judy is not impressed with these defendants from the jump. Even one of them going to pour himself some water irritates her.

Two college students moved into an apartment together. Judging by the amount of eye-rolling, it unsurprisingly did not end well. Plaintiff Raven Miyamoto loaned defendant Dache Williams money to cover her rent. She’s in court to collect that and additional costs. Instead of legal arguments, interpersonal drama takes center stage, with personal slights being made on both sides. The judge is predictably annoyed. But when Miyamoto decides to literally call “B.S.,” she seals her own fate. Swearing in the courtroom is not advised. When she repeats herself without a hint of shame, the judge knows all she needs to know about these two. The only one who calls B.S. in Judge Judy’s courtroom is Judge Judy.

Servers at the same restaurant moved in together. But the two started having arguments about cable costs and plaintiff Paige Morgan’s boyfriend living there without paying his share. When the judge directly asks him where he lives, Morgan’s partner stutters and stammers into an answer. Although she is the one being sued, the defendant’s countersuit over the plaintiff breaking open her bedroom door and pouring wet cereal on her property rings true. Morgan does get her rent money because of a lack of evidence, but she and her significant other don’t come off too well in the end.

Laken Pickrell sues her former roommates after being unfairly forced out of her apartment. She was thrown out and a false restraining order was issued against her. But defendants Francesca Ortega and her boyfriend, Martin Torres, can’t get their story straight. Ortega’s body language actually offends the judge immediately. Her constant interrupting and shady logic buries her credibility even further. Once Torres is left to his own devices and can’t tell the story she wants him to tell, Ortega tries to insert herself into the proceedings multiple times. She actually gets kicked out eventually. Their behavior in the courtroom does more for Pickrell’s case than even the evidence does.

These two were together for nearly a decade, but this case is more about who owns a shared property. Jesse Williams, Jr. and Michele Emmerick level all sorts of allegations once they get in front of the cameras. The thing is, Judge Sheindlin isn’t interested in petty and melodramatic squabbles. She also isn’t interested in their using orders of protection to try getting each other thrown out of their shared house. Emmerick’s belligerence even gets her removed from the court. Unfortunately, Judge Judy can’t undo their bad decisions, and has to send the plaintiff out without a satisfying resolution.

Right away, this case begins with a lie. The defendant attests she didn’t even live in the apartment she shared with the plaintiff for most of the time he says she did. So, the judge has to do what she does best and scare the truth out of her. Sheindlin starts pressing her about where she was living during the unaccounted months, and her shaky story starts to crumble. She doesn’t even have the good sense to panic either. Instead, she becomes smug with the judge and just smirks as she happily contradicts her own answer to the complaint.

Denise Silva moved into Charlotte Caron’s condo, paying some rent in advance. But Caron had Silva removed via restraining order and kept the money for the time she didn’t, or legally couldn’t, stay. Caron seems okay at the start. But as she gets going, she makes some strange statements that give us a window into what it might be like to share a place with her. Once she actually explains why she filed a restraining order, the judge isn’t just unconvinced — she’s offended. Judge Judy thinks it’s such an egregious overreach and misuse of the law that she awards Silva the small claims general maximum of $5,000.

It’s rare to hear Judge Judy swear. She’s someone who holds courtroom decorum in high esteem. But defendant Joshua Sumrow pushes the limit of her patience. Sumrow kept part of the security deposit from his coworker and roommate, withholding the money as he saw fit. However, things escalated months later when the plaintiff sued him. In response, Sumrow filed a protective order that would have gotten the plaintiff essentially barred from their shared job. It’s such a clear and inappropriate abuse of the system that the judge roasts him with the fire of a thousand suns.

In one of the saddest, most outrageous cases heard on the show, plaintiff Kyley Jones accuses defendant Octavia Camby of pouring a pot of boiling water on her while she slept. Camby, of course, asserts she didn’t attack her roommate. It comes out through the police and medical records that substance use on the night in question made Jones an unreliable witness to her own attack. Judge Judy is uncharacteristically empathetic towards the end of the case. She believes Jones’ story. She just couldn’t advocate for herself in her impaired state.

Karina Roy is a legend to any “Judge Judy” fan. The eponymous Tupperware Lady is on her own wavelength throughout this case. Her testimony concerning an argument with her ex-roommate over food storage receptacles is a stunning tour de force. She recreates the moment the defendant allegedly perpetrated a vicious Tupperware attack like she’s going for an Emmy. It almost makes us forget she’s talking about plastic food containers. Sheindlin’s patience is kind of astounding here. This eccentric plaintiff would probably be thrown out of the courtroom today. Then again, Judge Judy didn’t get this far by not knowing what good TV looks like.

Which of these cases had you reliving your worst roommate situation? Tell us in the comments.