Friday, June 26, 2026

Leonardo DiCaprio’s Art Advisor Latest in Long Line Who’ve Ripped Him Off Or Gone to Prison

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Leonardo Di Caprio is a great actor but maybe a poor judge of character.

Today, Lisa Schiff, his art advisor — for him and his foundation — was sentenced to two and a half years in prison for fraud.

Leo doesn’t learn his lesson.

In 2000, Dana Giacchetto — his best friend and investment counselor — went to prison for running a Ponzi scheme. He bilked his clients — including CAA’s Mike Ovitz, Tobey Maguire, the group Phish, and many others — to the tune of $14 million. (Many years later, Giacchetto committed suicide.)

In 2013, New York art dealer Helly Nahmad — still Leo’s pal — went to prison in a gambling scheme that was portrayed in the Jessica Chastain movie, “Molly’s Game.” He pleaded guilty to one federal count of operating an illegal sports gambling business. He was released after four months of a 12-month sentence.

And let’s not forget DiCaprio’s involvement in the 1MDB Malaysian finance scandal that involved ripping off public funds to back movies. Here’s a taste of that story.

Also, we still have no accounting or reporting for Leonardo’s charitable foundation. All the transactions are kept secret because the LDF’s records are hidden within a larger charity canvas.

The ironic thing here is that Leo has been in so many gangster movies, or films about criminals. He doesn’t seem to get it!

If Lisa Schiff is lucky, Leo will visit her with a screwdriver baked into a cake!

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Roger Friedman
Roger Friedman
Roger Friedman is the founder and editor-in-chief of Showbiz411. He wrote the FOX411 column on FoxNews.com from 1999 to 2009, where he covered Michael Jackson, and previously wrote the "Intelligencer" column at New York magazine in the mid-1990s, where he covered the O.J. Simpson trial. He also edited Fame 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. 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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