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Prophet and Loss

A manic money manager with a lust for celebrity, Dana Giacchetto played with Leo and Ben, Cameron and Courteney, while their millions were in safe keeping with his Cassandra Group. But when the party spun out of control, Giacchetto was the last to get the message.


"Will everyone just shut up!" The Times Square ball had dropped, and a minute into the millennium, Dana Giacchetto was struggling to quell the pandemonium in his 3,000-square-foot SoHo loft. Clutching a microphone in one hand and a paperback anthology of Greek plays in the other, the beleaguered money manager had planned to mark the occasion by reading a few portentous words to the 50 guests at his New Year's Eve party. But Giacchetto, who had named his Cassandra Group investment firm after the unheeded prophet, refused to start until his guests were focused on him.

"Just read and they'll shut up," advised a woman in black. Anxiously tugging at his Dolce & Gabbana T-shirt, Giacchetto launched into a passage from Aeschylus' Agamemnon, in which Cassandra declares that despite the machinations of her enemies, her legend will endure. "I am not like a bird," he intoned, "scared at an empty bush, trembling for nothing. Wait: When you shall see my death atoned with death . . . then witness for me -- these and all my prophecies were utter truth."

The performance, an observer would later note, was "pure Dana," a melodramatic tour de force that the 37-year-old Giacchetto intended as a rebuke to his ever-widening circle of antagonists. But most of the revelers, distracted by the televised vision of Dick Clark hugging a blonde, missed the analogy. Smiling weakly at the scattered applause, Giacchetto returned to D.J. duty, no doubt recalling that at last year's bash, it was rapper Q-Tip who was on hand to oversee the music. This time, Giacchetto told a guest, Q-Tip "couldn't make it." Neither could Winona Ryder, Matt Damon, Johnny Depp, or Ben Affleck, all of whom had been present last year. In fact, the lone celebrity in attendance was Alanis Morissette. "You know I'll never leave you," the singer cooed, wrapping her arms around her host. "You don't have to worry about me."

Dana Giacchetto was never the biggest money manager on Wall Street, but by the late nineties, the baby-faced broker was certainly among the most visible. Operating at the nexus of Wall Street and Hollywood, his SoHo-based Cassandra Group claimed to manage $400 million in assets for celebrities on both coasts. At one point, his client list ranged from brat packers like Tim Roth, Cameron Diaz, and Tobey Maguire to art-world stars like Ross Bleckner and David Salle to musicians like Morissette and Michael Stipe. Uniformed in Prada and Helmut Lang, his pet cockatoo perched on his shoulder, the darling of CNBC's Squawk Box became a tabloid staple along with his clients. Courteney Cox flew him home to meet her parents. Leo DiCaprio took him to Cuba. Michael Ovitz whisked him around Italy on his yacht.

Then, last autumn, the wunderkind whom GQ named the Rock-and-Roll Broker found himself in free fall. All summer long, there was growing buzz in New York and Hollywood that Giacchetto was in trouble. In early October, he was suddenly dumped by two of his closest allies, his partners in a $100 million venture-capital fund backed by Chase Manhattan, triggering a wave of defections from his money-management firm. On December 4, the Los Angeles Times broke the news that top clients were defecting because of undefined financial irregularities, and the article triggered a stampede: Seventeen clients left during a single week.

"I thought about it a lot, how all this could happen to me," he says. "You know, one day you're on top of the world, and the next, everyone's pissing on you."

But the worst blow was the suicide of his friend Jay Moloney in November. Against the advice of friends, Giacchetto had installed the talented but notoriously troubled agent as president of Paradise Music and Entertainment, a company Giacchetto funded with millions of his clients' dollars. Unable to overcome his addiction, Moloney had quietly stepped down last August; on November 16, he hung himself in the shower stall of his home. The night before Moloney's death, Giacchetto spent an hour on the phone with a "Page Six" reporter tearfully trying to kill an item about the agent's relapse.

"Jay's death nearly destroyed me," Giacchetto says. In the month after Moloney's funeral, he stopped going into the office and taking phone calls. Instead, he spent most of his time holed up in his apartment weeping over his mounting losses, both personal and professional. Then, just as his friends were planning an intervention, Giacchetto suddenly bounced back. "You can only lie back and take it for so long," he says. "At some point, you have to fight fire with fire."

Which is why, on a bitterly cold afternoon in January, Giacchetto is entertaining a reporter in his loft. Four minimalist couches form a square in the middle of the airy living room where his friend Leo once played video games before DiCaprio's attorney sent Dana a letter tersely cutting off all contact.

Keeping Dana company today are his new girlfriend, a pair of hyperactive cockatoos, and a newly hired publicist, Peter Brown, a sober, white-haired Brit who once represented the Beatles. "I thought about it a lot, how all this could happen to me," he says. "You know, one day you're on top of the world, and the next, everyone's pissing on you."

Even dressed in a conservative blue suit, he comes off like a precocious schoolboy, shifting in his seat and pulling on his hair as he makes the case that his troubles are a product of a "conspiracy" engineered by his former partners. "This was a power play," he tells me. "A campaign of misinformation against me by people I trusted. By people I thought were my friends."

The friends in question are Jeffrey Sachs and Sam Holdsworth, who were joined with Giacchetto in Cassandra-Chase Entertainment Partners, a $100 million venture-capital fund.

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