By 1995, he had charmed his way to the core of New York's downtown demimonde. "I met him at this birthday dinner for André Balazs," says another acquaintance. "There was James Truman, Lee Radziwill, and Dana. He was sitting across from this famous gossip columnist and telling him all about this money-management fund he'd started for musicians and artists who were friends of his."
On long weekend visits, Giacchetto set his sights on Hollywood, where he networked his way through a daisy chain of parties and premieres to the office of golden-girl producer Stacey Sher (Pulp Fiction, Get Shorty). Sher hung out with the under-30 crowd and dated a personal manager named Rick Yorn, who soon became one of Dana's closest friends.
Though most of Hollywood was paying Yorn little attention at the time, Giacchetto sized up the young manager's client base and recognized its potential. At the time, Yorn and his sister-in-law Julie Yorn had a lock on many young stars, including Cameron Diaz, Jennifer Lopez, Ed Burns, Matt Dillon, and Leonardo DiCaprio. In the face of Giacchetto's charm offensive, says one friend, "Rick didn't have a chance. Not only did Yorn invest his money with Cassandra, but he also encouraged each of his clients to do so as well."
Helped along by a spirited bull market, Giacchetto promised -- and frequently delivered -- returns of 40 percent and more for his clients. "Whatever he's doing, he's doing well for me," Courteney Cox gushed to the Post. "Every time everyone's panicking about the stock market going down, I just say, 'Go, Dana.' "
As his clients' portfolios took off, so did Giacchetto's cachet. He earned a reputation as someone who could put the right people in the right room -- usually his own loft. What he wanted to create more than an investment club, he says, was a salon of his generation's most important artists, writers, actors, and musicians. It was a "community," Giacchetto says, where ideas could cross-pollinate between rock and painting, movies and performance art, and Giacchetto would play matchmaker. Indeed, in 1994, he put together a deal that would stagger the industry -- and reveal a sharp edge to Giacchetto's laid-back demeanor.
"When Dana began showing up on 'Page Six' more than I did," Ed Burns told a friend, "I knew it was time to get out of there."
That year, Seattle's influential Sub Pop record label, which had nurtured such seminal grunge acts as Soundgarden and Nirvana, was looking for a major distribution deal. Acting as a high-paid auctioneer, Giacchetto frantically worked his Rolodex, talking up the label to David Geffen and Microsoft. "He'd have these meetings and say, 'If you don't want it, I've got three other people ready to take it right now,' " says a source close to the deal. "Then he'd turn around and start dialing the phone. He was a great negotiator that way. It's a certain magic and balls and timing."
After igniting a seven-month bidding war, Giacchetto delivered 49 percent of Sub Pop to Warner Music for $20 million. "That was just a phenomenal deal," says another insider. "The company was worth a couple million. That deal made people look at him in a whole new light." As reports of his deal-making abilities spread, other labels came calling -- followed by modeling agencies, hoteliers, magazine publishers, and movie studios. "I had an incredible amount of power," he says. "I could deliver anyone to anyone with one phone call."
Though she stuck with him throughout his rise, by 1998, the relentless networking eventually got to his longtime girlfriend, Artemis Willis. The couple sparred often and loudly over his "need to hang with the right crowd," says one pal. "Artemis couldn't stand the people around him. The constant name-dropping and social climbing started to wear her out." Finally, she moved out.
By all accounts, Giacchetto was devastated by the breakup, but his friends helped take away some of the sting. Prime among them was DiCaprio, who, by early 1998, was practically living in Giacchetto's loft. "Leo would wander down around noon, check the Bloomberg, make some calls, and they'd go out to a long lunch," recalls one former Cassandra trader. "Or Gwyneth would come by, and it was all hugs and kisses and 'Love ya, babe.' He was developing this whole cult of personality."
Though he was a decade older than some of the guys in DiCaprio's posse, at night Dana gamely played Pied Piper through the city's downtown club scene, from Cafeteria to Moomba to Veruka and back again. "He was out a lot," recalls a friend. "He'd always be asking, 'Where do we go next?' This was at two in the morning."
Eventually, however, his frenetic socializing took a toll. Sometimes Giacchetto didn't show up to work until 1 p.m., and he became less interested in the day-to-day operation of the Cassandra office, which had by then descended into comic disarray. He bought two cockatoos, one for himself and another for DiCaprio, which he allowed to fly loose through the office. Visitors would find the two birds, Tiberius and Angel, perched on the office's Bloomberg machine, chewing at the wires.
Clients complained that their monthly statements arrived chronically late, or not at all. After a couple of bad deals, including a disastrous foray into the now-bankrupt Iridium, many of them suspected that he was more concerned with maintaining his social profile than with monitoring their investments. His blatant self-promotion had also become an increasing liability. Sources close to Matt Damon and Ben Affleck say the actors decided to pull out because they thought Giacchetto was trading on their names for his own benefit. Another client, Ed Burns, followed them out the door for the same reason. "When Dana began showing up on 'Page Six' more than I did, I knew it was time to get out," he told a friend.
By now, Giacchetto was even dropping the names of clients he didn't have. He once showed a friend a spreadsheet with Steven Spielberg's name on it and claimed to be managing $7 million for the director. A source familiar with Spielberg's finances firmly denies he invested any money with Giacchetto. When informed of this, his pal laughs. "I knew that," he says. "Dana never thinks you'll like him enough."
Giacchetto denies he ever talks out of school about his clients and insists that complaints about his social life are wildly overblown."Look," he says, "I party, but mostly it was business. I'm not like a drug addict or anything. Far from it. I was here working my balls off every single day to make money for my clients and put deals together, and the proof is there. I finished all these deals. It's not like a smoke screen. I mean, I really did them. I'm really good at that."
Amid the circuslike environment, news that Giacchetto had taken on a new associate was greeted with some relief at Cassandra. A soft-spoken 47-year-old Richard Gere look-alike with an impressive political pedigree, Jeffrey Sachs was supposed to provide the ballast in Cassandra's flighty offices. Born to a Conservative Jewish family in the Five Towns and trained as a dentist, Sachs instead went into public service, landing high-profile jobs under governors Hugh Carey and Mario Cuomo.
Along the way, he developed a wealth of influential contacts. A close friend of John Kennedy Jr.'s (he was supposed to have been a passenger on JFK Jr.'s tragic last flight but canceled when he feel ill), he also helped Andrew Cuomo found help, the younger Cuomo's affordable-housing initiative.
At the time he and Giacchetto first discussed teaming up, Sachs was heading up a thriving consulting business that offered strategic planning for health-care groups, financial firms, and entertainment conglomerates, including Time Warner and NBC. "My biggest talent," he says, "was to make this happen or make that go away."