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Friday, March 21, 2025

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

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!

Roger Friedman
Roger Friedmanhttps://www.showbiz411.com
Roger Friedman began his Showbiz411 column in April 2009 after 10 years with Fox News, where he created the Fox411 column. His movie reviews are carried by Rotten Tomatoes, and he is a member of both the movie and TV branches of the Critics Choice Awards. His 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. He is also the writer and co-producer of "Only the Strong Survive," a selection of the Cannes, Sundance, and Telluride Film festivals, directed by DA Pennebaker and Chris Hegedus.

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