Six Insane Moments From THR's Profile of Leonardo DiCaprio's Convicted Ex-Money Manager

Wesley Mann
Dana Giacchetto

Dana Giacchetto tells THR of the sex, drugs and billions that made the '90s "a bacchanalian orgy" before he lost it all.

Dana Giacchetto regularly partied with his "little brother" Leonardo DiCaprio, managed money for Tobey Maguire, Cameron Diaz, Ben Affleck, Michael Ovitz and Michael Stipe, and says at one point he had roughly $5 billion under his control.

It all ended in 2000, when he plead guilty to fraud and was sentenced to 57 months in prison. In his first interview since 2003, Giacchetto recounts his wildest stories to The Hollywood Reporter's Tim Appelo and Gary Baum.

Read the complete story here and find six unbelievable highlights below.

1. Life was a "bacchanalian orgy for 10 years."

Giacchetto likes to think it was his time with DiCaprio that sparked the actor's interest in doing The Wolf of Wall Street, adding his own partying days were far worse.

"Listen, the sex and the drugs and the decadence in my life was 10 times worse [than Wolf of Wall Street], a bacchanalian orgy for 10 years. There was sex constantly [including $5,000 hookers], there were drugs constantly, but there was no sex without condoms."

2. The suicide of CAA's Jay Moloney brings him to tears.

Giacchetto says he isn't responsible for the death of CAA superstar Jay Moloney, though he acknowledges giving the former agent access to money, which he used for a drug binge that ultimately ended in his November 1999 suicide.

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"I killed him? It was his money," objects Giacchetto, breaking into what appear to be genuine tears. 
"If I didn’t give it to him, I would've gone to jail. I went to rehab with him [in New York], and then Uma [Thurman] and I, every week we're flying to [his rehab] in Minneapolis, praying at his bed, 'Please,
 Jay, what is wrong? I need you.'" 

3. Hollywood is full of "f---in' frauds," but Michael Ovitz is an exception.

"I would sit on his plane, and we would talk pure abstraction. … Ovitz was one of the very few intellectuals of Hollywood," says Giacchetto. "Most of those people are f---in' frauds. I started to get the Ovitzes of the world to say, 'This guy [may] be a flake, he may be effeminate, but he knows what he's f---in' doing.' I'm some crazy mathematical rock-star wacko who sold Sub Pop and Matador and made a lot of money."

4. DiCaprio spent Titanic's big night at Giacchetto's pad.

The night Titanic won 11 Oscars in 1998, DiCaprio skipped the ceremony; instead he and Giacchetto threw a party at the loft. "I was king of the world," says Giacchetto. "We projected the Academy Awards on the wall and had every star come to New York to give the middle finger because we felt the Academy Awards were a complete f---ing sellout and anti punk rock."

PHOTOS: Dana Giacchetto and His Celebrity Posse 

5. JFK Jr. once nearly fell from his penthouse window.

Giacchetto was used to entertaining notable partygoers such as Johnny Depp, Winona Ryder, Kate Moss, Michael Stipe and Mark Wahlberg, but one night, John F. Kennedy Jr. showed up and gave partygoers a scare.

"I had all my windows open, and John F. Kennedy Jr. was standing there," says Giacchetto. "Everyone's like, 'Don't fall out that f---in' window!'" JFK Jr., as it happened, died in a plane crash en route to his cousin Rory's wedding to Mark Bailey, who worked for Giacchetto's business partner Jeffrey Sachs.

6. Perhaps his best business deal centered on Nirvana.

Giacchetto parlayed Nirvana's success into a $20 million payday for the band's first label, Sub Pop. He organized the Seattle label's sale to Warner Music Group for many times its expected value.

Click here for more wild tales from Giacchetto.