In the mid 1990s, Leonardo DiCaprio was the king of the world. The baby-faced movie star was about to play the leading role in Titanic, and he spent some of his time hanging with Dana Giacchetto, a former investment banker and member of the new wave group Breakfast in Bed, at Giacchetto's penthouse loft on Broadway and Cortlandt in Manhattan. The two friends owned matching cockatoos named Angel and Caesar and hosted lavish parties for the most powerful people in 90s film, fashion, and finance: Michael Stipe, Andrew Cuomo, Kate Moss, Winona Ryder, Harmony Korine, and Alanis Morissette, among other celebrities. In between doing the things that happen at late-night parties, including spraying vintage champagne everywhere, some guests made million-dollar late-night deals—at least that's what Giacchetto claims. His high life crashed down on him when he was arrested in 2000 and pleaded guilty to fraud under the Investment Advisers Act. After that, most of his clients left him, and the court sentenced him to a maximum of 57 months in prison for misappropriating approximately $9 million. Thanks to good behavior, time already served in prison, and his willingness to enter rehab, he was released early, but his life has never been the same. Giacchetto's downfall began in 1988, when his mother, Alma, loaned him almost $200,000 so he could found the Cassandra Group. Giacchetto already worked as an account executive at Boston Safe Deposit & Trust, and he used his bona fides to persuade friends in new wave and punk bands to put money in an investment group for cool, arty people. Thanks to his business skills and rock cred, Giacchetto started working with Sub Pop Records, the iconic indie label that was simultaneously broke and famous for releasing Nirvana's first album, Bleach. Soon after, Giacchetto worked as the money manager for all of Sub Pop's acts, as well as for the Smashing Pumpkins, Alanis Morissette, Phish, Victoria Williams, Q-Tip, R.E.M., and many of their agents and managers. Giacchetto went to prison for stealing $9 million from a number of these clients, including Phish, who lost more than $1 million, according to the New York Times. The Securities and Exchange Commission had discovered improprieties in Cassandra's bookkeeping dating back to September 1997. (Giacchetto had used a version of the classic "asset-kiting scheme," in which one asset is borrowed to cover the disappearance of another.) Prosecutors alleged that Giacchetto's scheme involved improperly tapping into the accounts of the Cassandra Group's clients and ordering checks from financial services firm Brown & Co. He was able to cash them at the US Trust even though some checks were made out to celebrities like Ben Stiller. "I was someone who was extraordinarily successful, beyond his wildest dreams, and I flew too close to the sun and, you know, got really burned," he told us when we met him in New York this summer. After telling us he didn't have too much time to talk because he had to meet with his lawyer and the FBI, he insisted on his innocence and maintained that he had been accused and convicted because Hollywood insiders were trying to keep him out of the elite, high-powered, celebrity life of Hollywood that he saw as a kind of Mount Olympus. "I think that there is some truth in the idea that there is this vapid vacuum still that is Hollywood—sometimes because it's a business built on artifice, fantasy," he said. "It doesn't mean that it's not legitimate. It just means that, contextually, you have to sort of put it into place, and I think people do get envious of that." At every meeting, Giacchetto promised us he would bring photos from his years with DiCaprio. We didn't believe him, but at our last interview, Giacchetto brought a Travelpro expandable luggage bag full of hundreds of photos, like these pictures of DiCaprio partying. As Giacchetto flipped through the pictures, he reminded us of a father showing photos of his children, not because Giacchetto liked bragging about his 90s debauchery but because these celebrities were once his friends. When he went to jail, many of them abandoned him. This hasn't stopped Giacchetto from doing business with the rich and famous, of course. Along with his phone-app gig with Pavitt, he's repping a new line of luxury food items that will enable you to eat lobster thermidor straight from the can. Check out more episodes of The Real: http://bit.ly/The-Real Watch "The Real Walter White" - http://bit.ly/1xBZvyr Click here to subscribe to VICE: http://bit.ly/Subscribe-to-VICE Check out our full video catalog: http://bit.ly/VICE-Videos Videos, daily editorial and more: http://vice.com Like VICE on Facebook: http://fb.com/vice Follow VICE on Twitter: http://twitter.com/vice Read our Tumblr: http://vicemag.tumblr.com Follow us on Instagram: http://instagram.com/vice

• published: 21 Nov 2014
• views: 1730516