Comedian Chris Distefano is no stranger to pushing boundaries but his recent birthday roast for billionaire New York Mets’ owner Steve Cohen almost crossed a line he “almost” couldn’t come back from. In his recent appearance on the Joe Rogan Experience podcast, the comic revealed how a seemingly innocuous gig turned into a legal nightmare involving NDAs, angry lawyers, and a close call that could have tanked his career and maybe even the entire trajectory of his life.

Distefano’s troubles began immediately after his performance for Cohen’s kept-under-the-wrap birthday bash. The reason? The comedian went to a restaurant during the pandemic, called up by Lady Cohen as a nice little birthday surprise. But, Steve Cohen was busy hanging out with his friends, none of whom were very receptive to Distefano’s presence. The night took a surprise turn, however, when the Mets’ owner himself took the matter into his own hands. 

Steve Cohen offered the comedian a deal—get his gig pay doubled at a go—only if he could make Cohen and Co. laugh. And oh, laugh they did! And the money, Distefano got. Further, he got a bunch of NDAs to sign on, considering it was peak COVID time and the gang was celebrating in a public restaurant. This meant that the comedian was not supposed to talk to anybody, let alone the media about what went down that night, only if the guy knew that himself.

Narrating the incident on the Joe Rogan Experience Podcast, Distefano said he shared the story on Sal Vulcano’s “Hey Babe” podcast, opening with a bombarding line of “Dude… I f*cking hated it last night! Here’s the story.”

A day later, his manager was in a panic, calling him up from his sleep and asking him to take the episode down at once. “You broke, you violated the NDAs, you just said all these things about the Cohen gig; you can’t do that!” his manager warned. Facing threats of a lawsuit that “they will not lose,” Distefano found himself in a perplexing and stressful place. That stress didn’t last for long, though.

Distefano, scrolling Instagram, discovered messages of support from the Cohen family themselves. “I can’t believe you talked about it!” “Hey, babe, we loved it!” “That’s amazing; my dad’s dying laughing!” Steve Cohen’s wife, daughter, and son were thrilled by his performance, contradicting the frantic warnings from his legal team. Cohen wasn’t done with him just yet, though.

How exactly did Steve Cohen make Chris Distefano redeem himself?

After the NDA scare was nullified by Cohen’s own family, Distefano quickly took to his manager, prompting swift action. Within minutes, the lawyers backed off. It turned out the entire debacle was a misunderstanding—Cohen himself hadn’t directed the legal action. And now the whole family has befriended the fated comedian. Still, he owed Cohen something for not keeping his word. And Mr. Cohen would be the last one to let something slide that easily.

So, Steve Cohen, in a playful twist, offered Distefano a chance for redemption during a baseball game. Should a rain delay hit a Mets game, he’ll give the comedian five minutes on the mic to entertain a likely disgruntled crowd of wet fans. “You want me to do five minutes, to cold, wet, Mets fans that are angry, about the team not playing?” Distefano mused, ultimately accepting the challenge.

Distefano’s hilarious saga highlights the high-stakes world of comedic roasting, particularly when the target is a powerful billionaire. It raises questions about the limits of humor, the fine line between NDAs and censorship, and the delicate balance between legal agreements and the unexpected support of the very people you’re joking about.