Bon Vivants and Billionaires: Living Large With Leo

Paramount Pictures
'The Wolf of Wall Street'

The Oscar winner has developed a rich — and occasionally infamous — circle of friends over the years. Here’s a rundown of some of the high rollers who have penetrated DiCaprio's exclusive orbit.

Aesop probably wasn’t considering the world of celebrity and superstardom when he wrote the proverb, "A man is known by the company he keeps." But anyone wanting to peer into the secretive world of Leonardo DiCaprio may find it easier to examine the figures in his orbit (and we don’t mean the supermodels). While the Malaysian businessman Jho Low might currently be the most notorious buddy, dragging DiCaprio into the 1MDB corruption scandal in which The Wolf of Wall Street is now embroiled and a $1 billion filing by the Department of Justice, he’s not the only international billionaire on the list. And he’s not the only one with the odd legal curiosity on his CV.


Aziz, the stepson of the Malaysian prime minister, is alleged by the Justice Department to have used funds siphoned from the country’s sovereign wealth fund 1MDB to set up Red Granite Pictures and finance DiCaprio's passion project The Wolf of Wall Street. But it wasn’t purely Hollywood ambitions that were given an — alleged — helping hand, with $40 million worth of luxury properties in New York and California owned by Aziz also now facing seizure by the DOJ. Kentucky-born McFarland, who co-founded Red Granite with Aziz, may not have any assets listed in the DOJ forfeiture filing, but was an ever-present figure at champagne-fueled parties and gambling jaunts.


The Manhattan nightclub impresario, whose portfolio includes 1OAK, Butter and Up & Down, is DiCaprio’s long-standing party hookup, from New York to L.A. to St. Tropez. (Sources say he helps “cast” the LDF gala with stunning women.) When Rihanna isn’t rumored to be with DiCaprio, she’s rumored to be with Akiva.


Tagged as the “homeless billionaire” for swapping his luxury homes in Miami and Manhattan to instead slum it in luxury hotels and aboard his Gulfstream jet, Berggruen — who reportedly turned $250,000 from his art-dealer father (a close friend of Picasso) into $2.5 billion — has been rubbing shoulders with DiCaprio for years, hosting the star at his annual Oscars bash in the Chateau Marmont (one of a number of parties awash in celebrities and statesmen he regularly throws). Earlier this year, he splashed out more than $45 million for 450 acres in the Santa Monica Mountains on which he hopes to house his Berggruen Institute think tank.


Once labeled Russia’s answer to Donald Trump (for his hotels, not dubious hair or political ambitions), this former trader turned billionaire property developer has regularly hosted a holidaying DiCaprio and supermodel du jour on the top deck of his luxury yacht. Alongside his international real estate holdings (including Moscow’s OKO Tower, currently Europe’s tallest building) Doronin owns the Aman Resorts group, the ultra-luxe hotel operator favored by billionaires, royalty and celebrities (Leo is a fan). However, the 2013 purchase of the resorts wasn’t an entirely smooth affair, with Vlad falling out in rather dramatic fashion with his partner on the $358 million deal, U.S. entrepreneur Omar Amanat, amid allegations including fraud and extortion. (The suit was eventually resolved by the London High Court, with Doronin  retaining full control and ownership of Aman.)


DiCaprio ditched 1998’s Titanic-dominating Oscar ceremony, which he instead watched from the New York apartment of the famed "stockbroker to the stars," scene for many a notorious, debauched A-list party. Giacchetto had taken a young Leo under his wing, holidaying with the rising star, gifting him with art and letting him stay at his SoHo penthouse (where they had matching cockatoos). But his celebrity empire came crashing down in 2001 when he was arrested for fraud involving his clients’ funds and sentenced to 57 months in prison. He died earlier this year.


The alleged kingpin in the 1MDB corruption scandal, Low is alleged to have embezzled hundreds of millions of dollars, supposedly destined for a Malaysian sovereign wealth fund, into his personal property portfolio and art collection. Low became renowned on the New York and Vegas clubbing scenes in 2009 for a throwing a series of champagne- and celebrity-strewn parties and for attracting a growing cohort of stars into his expensive orbit. One of the A-listers in his crosshairs was DiCaprio, who became a regular at his side and recipient of his generosity. It was Low who introduced the actor to Riza Aziz and Joey McFarland, who would produce his passion project The Wolf of Wall Street (with money alleged to have been diverted from Malaysia via a series of transactions), and was later thanked by DiCaprio at the Golden Globes and in the film’s credits. Now a major name cited in a $1 billion Department of Justice asset seizure complaint, Low is currently believed to be hiding out in Taiwan.


The billionaire art dealer (son of David Nahmad, currently No. 959 on Forbes’ list) was in 2013 sentenced to 12 months in prison for operating an illegal $100 million gambling ring from his Trump Tower flat. The high-stakes business catered to professional players, millionaires and celebrities, including his close pal DiCaprio. After securing an early release in 2014, Nahmed was transferred to a halfway house in the Bronx, and was allowed by a judge to attend last year’s Art Basel fair, alongside DiCaprio, where he was selling a piece by Rothko for $50 million.

A version of this story first appeared in the Aug. 26 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.