Ray William Johnson: True Story Podcast - He's Addicted to Prostitutes - The Jonathan Crupi Story

Episode Date: March 16, 2026

Jonathan Crupi was a Brooklyn high school English teacher who, on July 5, 2012, murdered his wife and fellow teacher, Simeonette Mapes-Crupi, in their Staten Island home.

So this guy is addicted to hookers, and it's gonna cost him everything. Now the guy's name is Croopee, and Crupi is about 26 years old when all this starts, and he's living in New York. But see, Cruppy has a problem. He's addicted to adult media. You know, images and videos of individuals having intercourse, which wouldn't be that big of a deal, except that this woman is in his life. Her name's Sissy, and Sissy is CooPie's wife. And of course, Krupy isn't telling her about his addiction.

He's keeping that a secret. And none of this seems to affect their marriage, so, you know, no harm, no foul. But one day, around 2008, all that changes. Because Kruppy gets hired to work at the local high school that Sissy teaches at, and he starts teaching English classes there. And this, it works out well for him. Sissy and Kruppy, they're both really popular teachers. All the students love him because I guess they think he's a fuller.

funny guy. But he's only teaching there on a probationary period. The thing is, in New York, to be a full-time teacher, you have to get your master's degree. And Crupi doesn't have his master's yet, but he's allowed to pursue it while he's getting started teaching. The only problem with that is that the dude is kind of broke. Like he doesn't have the money to go back to college, and college is expensive. But his wife, Sissy, believes in him, and she agrees to pay for it. because, you know, she's getting money from her parents. So Crupy and Cissy enroll in a local college, because they're both going to work on getting their masters.

And when the semester starts and it's time to go to class, Sissy shows up on time and she does really well in her classes. But Cruppy doesn't. He doesn't show up to his classes at all. Instead, he actually takes that tuition money that Cissy's giving him and he uses it to subscribe to a bunch of adult websites and he also spends a lot of it at local strip clubs, Just tipping strippers with his tuition money.

And over time, I guess, he decides that the websites and strip clubs aren't satisfying enough for him, and he starts using that money to purchase prostitutes. And it's around 2009 when he meets a hooker who will become his favorite, Miss Pumpkin. And I don't know why she calls herself Miss Pumpkin, but that's what she calls herself. So Crupy pays Miss Pumpkin money, and they start smashing. And soon, it becomes a... regular thing, like they're meeting every six to eight weeks to hook up. Sometimes he'll even wait until Sissy isn't home and then he'll bring Miss Pumpkin over to their house and they'll smash there.

So while Sissy is spending all her money on bills and food and paying for them to both complete their education, Cruppy just keeps spending all his money and the money that Sissy's giving him on adult websites and strip clubs and smashing with hookers. And three years pass and it's now 2012, and it's around this time that all of this starts to fall apart. Because Sissy, she starts getting suspicious of Crupy. So she goes through his phone and she finds a number that she doesn't recognize. Then she does a reverse search on that number and she can see that it belongs to another woman, that woman being Miss Pumpkin. So Sissy gets super pissed off and rightfully so. I mean, she feels betrayed. And so she starts looking up information about

marital separation because she's making plans to leave croupy. And around this time, she ends up getting a letter in the mail, letting her know that she has officially graduated with honors. So now she has her master's degree. But then she notices that Crupey didn't get such a letter. He didn't get any letter at all. So she investigates. I assume she calls the college. And that is when she learns that not only did Crupi never graduate, but he never even attended classes. Not only that, but she also learns that he had taken more than $50,000 that her parents gave her to give to him for tuition

and he spent it on strip clubs and hookers. And if that isn't bad enough for Crupy, then the principal of the high school that they work at notice that he still hasn't earned his master's degree so he gives him an ultimatum. Get your degree or your fire. So Crupy's entire life is about to collapse, and here is where things get really dark. One morning, Cissy decides that it's time to confront her husband about all of this, about the lying, about him stealing the tuition money and spending it on smashing.

And as soon as he wakes up, she lays into him, and she tells him that she knows everything he's been up to and that she's going to leave him. And Crupe, he doesn't take this well. He freaking snaps, and they start yelling at each other, and suddenly, boom, he pushes Sissy down the stairs, and this knocks her out of commission. Then, Crupi goes, and he gets a knife, and he stabs her over and over again, 15 times. And this ends up killing her. So now, Cruppy has to figure out how to cover this up, and he decides, oh, I'll just make this look like a robbery gone wrong. So he starts trashing the house and trying to make it look like a burglar broke in. Then he leaves, and he goes out and he starts running errands and making sure that he's on different security cameras.

Like he goes to buy movie tickets, he buys some new shoes, he gets his car inspected, he stops by the school where they work, and while he's doing all that, I guess he gets in the mood to smash. So he gets on his computer and he looks up some escort sites, but ultimately he decides that he wants to just go with his favorite. and he calls up Miss Pumpkin. And then they meet up at a local motel and they smash. And when they're done, he goes back home and he finds his wife's body there and he finally calls 911 and he pretends to be shocked. And pretty quickly, police arrive and they start investigating. And of course, they ask Crupi where he's been today and he gives them a list of all the activities that he's been doing.

And so they go and they check it all out and they find him on. different security cameras at all those places he went to. So it's looking like Croopy might actually get away with all this as long as he didn't screw anything up. Until. Three days after the murder, Cruppy moves back in with his parents. Even so, he's still seeing Miss Pumpkin on the regular. And at one point, he meets with her and he tells her that his wife was recently murdered and that he doesn't know why someone would do that and he like acts all emotional about it. But he also mentions that the murder happened on the day that they met up to smash at that local motel. And he also tells her that he lied to the police about

where he was that day. Meanwhile, the police are still investigating, but they haven't made much progress. But then they get into Sissy's phone. And there, they find a phone number saved under the name, Woman, and they track it down to Miss Pumpkin. Apparently, Sissy had gotten Ms. Pumpkin's phone number from Crupy's phone, and she had saved it into her own phone. And so, police go and they question Miss Pumpkin. And she immediately tells them that, yeah, she and Crupy met up the day of the murder, and they smashed. And so now, police are really suspicious of Crupy, because, you know, he lied. And so eventually, they get a warrant to search his computer, and there they find his Google searches for things like how to cut a throat, how to break a neck,

and how to clean up a crime scene. And that's all on top of his searches for adult websites and escort sites. So now they have all the evidence they need, and so bam, they arrest croupy. Here's his mugshot. And ultimately, he goes to trial, and he's found guilty, and he gets sentenced to 25 years to life in prison.