Movies & TV

The Crazy Story Of How A Con Artist Tricked His Way Into Leonardo DiCaprio's Inner Circle

A new book reveals how showering the actor with gifts won his friendship in one of the biggest fraud cases in U.S. history
IMAGE Esquire UK/Getty

As you may know, Leonardo DiCaprio is rarely seen without his trademark postboy hat in order to fly under the radar. The actor just wants to live a quiet life away from the chancers always trying to get a slice of him in the real world.

It comes as some surprise, then, that according to new book called Billion Dollar Whale: The Man Who Fooled Wall Street, Hollywood, and the World, Leo recently found himself at the center of one of the biggest fraud cases in U.S. history after a Hollywood wannabe infiltrated his sacred inner circle.

The book, by Tom Wright and Bradley Hope, tells the story of Malaysian financier Jho Low who stole billions from a state fund intended to develop the country and threw wild parties with, among other things, Kanye West performing. He met DiCaprio through talent booker Joey McFarland and proceeded to woo the actor with outrageous gifts and even financed DiCaprio's film, The Wolf Of Wall Street. 

Here are five of the best revelations about how Leo fell victim to a classic tale of grifting.

Leo has a wingman break the ice with women

The story starts in 2010 where, at a nightclub called Taboo in Johannesburg, Leo was in attendance and spotted TV personality Aimee Sadie. According to The Hollywood Reporter, who have published excerpts from the book, McFarland approached Sadie and said, “Would you like to join us in the VIP? Leonardo DiCaprio is there and he’s been eyeing you.

While we're not saying we thought Leo's modus operandi when on the pull was summoning people with a vape revolver, we had imagined the guy who has been through a baseball team's worth of Victoria's Secret models to have a more impressive ice breaker than shoving his mate in their direction.


The way to Leo's heart is art, apparently

As well as funding the aforementioned trip to South Africa, Low showered the actor with outrageous gifts, even for someone as famous as DiCaprio.

They included, "a $3.3?million painting by Pablo Picasso as a late birthday present", a $9.2?million Basquiat collage entitled Red Man One, and even Marlon Brando’s Oscar for On the Waterfront.

Elsewhere in the book Wright and Hope reveal that Low had a penchant for grand gestures, giving model Miranda Kerr a $1.3m diamond necklace and reportedly paying Paris Hilton around $100,000 to attend his parties.

Both Kerr and DiCaprio voluntarily surrendered the gifts from Low and producers of The Wolf of Wall Street were forced to hand over $60 million to the US government to settle a civil lawsuit.

Leo loves a grifter story himself

In discussing why DiCaprio was drawn to the story of Jordan Belfortthe stockbroker who ran a penny-stock scam and was the basis for The Wolf Of Wall StreetWright and Hope's book says that Leo just can't resist a well executed scam.

Recommended Videos

"Belfort intrigued DiCaprio, who had made Catch Me If You Can, about master impersonator Frank Abagnale Jr., and, at this time in 2010, was about to sign on to play Jay Gatsby in Baz Luhrmann’s The Great Gatsby."

The fact he has played a series of con artists does make it all the more ridiculous that he didn't suss the huge con going on under his nose. Maybe Leo can play himself in the movie!

Read the full story here.

This story originally appeared on

* Minor edits have been made by the editors.

View More Articles About:
More Videos You Can Watch
About The Author
Olivia Ovenden
Senior Digital Writer
View Other Articles From Olivia
Latest Feed
Load More Articles
Connect With Us