Tuesday, June 2, 2026

Leonardo DiCaprio’s Second BFF Gets a Federal Prison Term

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Leonardo DiCaprio does not have an Oscar. But he does have the distinction of being the only major box office star to have two different friends sent to federal prison. And it’s only within a 14 year time frame.

Leo’s BFF, art dealer Helly Nahmad, got a 366 day sentence yesterday in Manhattan federal court for participating in wide spread gambling scheme. Nahmad, 35, used over a $1 million from his father’s Madison Avenue art gallery to get involved with Russian gangsters.

Nahmad had proposed not going to jail but donating $100,000 a year to education programs. Judge Jesse Fuhrman wasn’t having it. At the sentencing the Judge said: “There is only one way for Mr. Nahmad to understand his actions have consequences … and that is to send him to prison.”

The judge observed of Nahmad’s proposal: “Doing good works before sentencing is as low-hanging fruit as it comes and he didn’t pick it,” the judge said. “It kind of baffles me, to be completely honest.”

Nahmad has been BFF with DiCaprio for several years, traveling with him all over the world. He was still part of DiCaprio’s entourage this past winter during the Oscar campaign for “Wolf of Wall Street.”

This isn’t Leo’s first pal to go to the slammer. In 2000, his erstwhile business manager Dana Giacchetto was sentenced to five years in prison on multiple counts of fraud. He was ordered to pay $14 million in restitution to his victims for subjecting them to his Ponzi scheme. The victims are still waiting.

Nahmad may not have learned his lesson. According to Bloomberg News: The judge said he was troubled by a secretly recorded call made by U.S. investigators in which Nahmad can be heard saying he would sell a Raoul Dufy painting at a price that was inflated by $50,000 and that he would split a $25,000 profit with another member of the gambling ring. Nahmad can be heard bragging that he was “raping” the buyer for the profit.

As part of Nahmad’s plea agreement, he forfeits $6.4 million and rights to the Dufy painting. He must turn himself in by June 16th to Otisville Prison in upstate New York.

The Nahmad Gallery, at the Carlyle Hotel, is still in business despite rumors that the scandal shut it down. Nahmad’s lawyers said at the sentencing that he’d lost his lease. In any case, the business built and run by his father until Nahmad Jr took over, is suffering in the aftermath of his notoriety.

 

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Roger Friedman
Roger Friedmanhttps://www.showbiz411.com
Roger Friedman is the founder and editor-in-chief of Showbiz411. He wrote the FOX411 column on FoxNews.com from 1999 to 2009 and previously edited Fame magazine and wrote the "Intelligencer" column at New York magazine. His bylines have appeared in The New York Times, The Washington Post, the New York Daily News, the New York Post, Vogue, Details, and the Miami Herald. He is a voting member of the Critics Choice Awards (Film and Television branches), and his movie reviews are tracked by Rotten Tomatoes. is articles have appeared in dozens of publications over the years including New York Magazine, where he wrote the Intelligencer column in the mid 90s and covered the OJ Simpson trial, and Fox News (when it wasn't so crazy) where he covered Michael Jackson. With D.A. Pennebaker and Chris Hegedus, he co-produced the 2002 documentary "Only the Strong Survive," which screened at Directors' Fortnight at the Cannes Film Festival.

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