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Prophet and Loss

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On December 13, Giacchetto filed suit against Sachs, Holdsworth, Chase, and another Cassandra-Chase associate, Robert Egan, charging that they had conspired to eject him from the partnership by ruining his reputation. The suit seeks $100 million in damages and the full dissolution of the Cassandra-Chase partnership, plus repayment of $600,000 Giacchetto says he laid out in rent and expenses.

In his suit, Giacchetto charges that about a year ago, Sachs and Holdsworth started "intentionally, willfully and maliciously" spreading false rumors about him to Hollywood insiders such as DiCaprio's lawyer Steve Warren. He charges that Sachs told Warren and others that Giacchetto "was going to get arrested," that he was being investigated by both the SEC and the FBI. As a result, the suit continues, DiCaprio terminated his account at Cassandra.

"I've heard all kinds of slanderous rumors," Giacchetto says. "That I'm going to jail. That I'm about to be indicted. It's all lies! It's all so dark, I don't want to believe it's true."

Holdsworth and Sachs declined to discuss the charges, but their attorney, former governor Mario Cuomo, who was once Sachs's boss, filed papers last Friday asking the court to dismiss Giacchetto's suit. They claim Giacchetto's allegations are baseless and his problems self-created; they also demand repayment of $950,000 loaned to Giacchetto when his troubles began.

In any case, it seems the manic money manager's troubles are far from over. New York has learned that the Securities and Exchange Commission recently spent six weeks poring over Giacchetto's books. A former vice-president at Cassandra was interviewed by the U.S. Attorney's office about alleged criminal activity at the Cassandra Group. The government's inquiry, says a source close to the situation, centers on charges that Giacchetto misdirected client funds and misled clients about the amount of money in their portfolios. Giacchetto angrily denies reports of any such investigation. The U.S. Attorney's office declines to comment.

But even his staunchest critics doubt he profited personally from his actions. After all, he considered himself an artist, serving creative soulmates. The consensus seems to be that at some point, Giacchetto, by all accounts a savvy and accomplished investor, lost his way, and unwilling to let down his high-profile clients, struggled to cover his tracks. "This is a naïve individual with very good intentions who simply went out of control," says one associate. "Dana didn't know how to put the brakes on, because he only has an accelerator."

Dana Giacchetto was raised in the Boston suburb of Medford, the oldest son of middle-class parents. His first business enterprise was selling magazines door-to-door when he was 11. "The very first door he knocked on, the woman said no and he ran back home crying," recalls his father, Cosmo, a real-estate broker. "I had to tell him, 'They're not rejecting you; they're rejecting what you're selling.' Dana is a real hustler, but he feels bad when people say no."

After showing early promise on the piano, Giacchetto took lessons and faithfully practiced on the family's upright thirties Fischer. By the time Dana was in his teens, he was staging concerts by his pop band in the family rec room and recording their songs on an eight-track. "He should have made it as a rock star," sighs his father. It wasn't for lack of trying: At the University of Massachusetts in the early eighties, Giacchetto fronted two successive bands that drew a large following in Boston. But his rock career never really took off.

Instead, Giacchetto landed a job as an analyst for the white-shoe Boston Safe & Deposit Company, trading by day and playing gigs late into the night. In a scathing article last December, the New York Observer reported that the company had no record of his employment there. But a spokesman for Boston Safe confirms that Giacchetto was employed there full-time from 1980 to 1987; his former boss, Donna Wong, now works as a systems analyst at Cassandra. The Observer was also unable to find any record of the business courses Giacchetto claimed he took at Harvard. As it turns out, Harvard does have a record of Giacchetto's attendance, but the courses were at Harvard's extension school, not its prestigious business school, as he had claimed.

When Giacchetto left Boston Safe in 1987 to strike out on his own, many of his devoted clients followed suit. Cassandra targeted creative types with a simple pitch: Since artists, actors, musicians, and filmmakers are paid only sporadically for their work, they require specialized investment strategies. Giacchetto's approach was long-term, ultraconservative. "I never started Cassandra thinking, I want to make tons of money," he says. "I started it because I really believe that most of the creative people I knew were ill-advised and didn't have any resources. I thought I could help them find a safe way to grow their money."

Though he'd given up performing, he still thought of himself as an artist, with money his new medium. "When I meet money managers who tell me they're technicians, or it's about science, that's bullshit," he says. "You don't know if a stock is going up or down tomorrow. It's an art, just like writing a song or doing a painting."

To woo his artsy clients, he and his then girlfriend, Artemis Bradford Willis, held dance parties on the rooftop deck of his Back Bay apartment and followed up with a monthly newsletter that offered investment tips along with gallery listings and art reviews. By the early nineties, he was one of the best-known brokers in Boston, but typically, he was restless. Packing up his spreadsheets, client lists, and even the family's Fischer piano, Giacchetto moved to New York, and from his loft on Lafayette Street he began his most ambitious assault.

After relentlessly cold-calling the powerful PaceWildenstein Gallery, he wrangled an audience with its influential president, Marc Glimcher. Amused by the quirky hustler, Glimcher took Giacchetto under his wing, introducing him to art-world players like George Condo and Bleckner, who became his earliest clients.

It was his personality as much his business acumen that drew people to Giacchetto. "He'd stare adoringly into your eyes, loving everything you said," notes a former client. "He has this wonderment that disarms people. An innocence he exudes."


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