Friday, June 5, 2026

Jail Time: Leo DiCaprio’s BFF Gets Out Early, Madoff’s Secretary is Going In

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Helly Nahmad is out of the clinker. Leonardo DiCaprio’s best friend– and his second friend to go to federal prison– is out and about. The New York Observer reports that Helly got out early. He only served five months of a one year-and-a-day sentence, is now in a Bronx half way house. He may come and go to work, and soon will be free to resume his high flying life.

Benjamin Brafman represented him, the same guy who got Diddy/Sean Combs out of his famous shoot-em-up deal years ago. If you’re ever in trouble and can post Brafman’s retainer, he’s the guy. Art dealer Helly participated in a worldwide gambling scheme. He used $1.5 million of his dad’s money to do it. And yet, the Nahmad Gallery is booming award at Madison and 76th. They had a big set up at Art Basel, and even bigger one in Paris at FIAC.

Anyway, jail is so boring. By New Year’s we’ll see Helly in pix from St. Bart’s. Justice!…

Meantime, Annette Bongiorno, Bernie Madoff’s assistant, is going to jail for six years. The judge said she knew exactly what was going on, or looked away so Madoff could get away with his crimes. The six year sentence is short, but so is Bongiorno. The judge said he was being lenient because Bongiorno’s height could get her into trouble in jail. Keep that in mind, all short people, when you’re thinking of breaking federal laws!

Meantime, innocent people with no money go to prison for years. They either die there or are saved by the Innocence Project. Then they get out of jail and die. That is life.

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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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