Postscript: Dana Does Detention

Allegra Brosco was not the sort of woman who had ever imagined herself married to a convict. Still, when Dana Giacchetto suddenly popped the question last August, during her weekly jailhouse visit, Brosco pondered for just a few minutes before saying yes.

It was, she admits, an inauspicious debut to a lifelong commitment, but in her retelling it seems dangerous and romantic – like a scene from a Brontë novel. “There was a guard who was watching to make sure we didn’t get too close,” she remembers. “And all around us these sad, tired people. I didn’t want to get tossed out, so we just pressed our foreheads together and cried.” When he proposed, they had been a couple for eleven months.

During that time, Giacchetto, the manic, starstruck money manager, pleaded guilty to one count of fraud. Due to be sentenced on January 17, he faces 46 to 57 months in jail. The couple initially resolved to marry in prison, a plan they’ve since reconsidered. “Both our parents were against it,” Brosco explains. “And we’ve caused them enough pain already.”

There has been, amid the torrent of press documenting the fall of Dana Giacchetto, little mention of Allegra Brosco, the 32-year-old woman who had the closest view of his spectacular flameout and stuck around to help clean up the mess. When they began dating, Giacchetto was at the top of his game, a millionaire investment whiz and offbeat guru to an adoring flock of movie stars, musicians, and media types. As head of the $100 million Cassandra Group, he spent his days managing funds for clients like Leonardo DiCaprio, Q-Tip, and Michael Stipe, his nights picking up their tabs at Moomba and Lot 61.

Disarmingly down-to-earth and unfussily attractive, Brosco seemed out of place among the glossy starlets and socialites in Giacchetto’s orbit. She’d moved to New York four years earlier, following a brief marriage to a Boston doctor, determined to become a film producer. She worked as a personal assistant to Ted Hope, co-founder of indie production company Good Machine, and lived for three years with a promising young filmmaker in TriBeCa.

Brosco claims that Giacchetto, who traveled constantly, always stockpiled airline tickets so he could have them readily available. She has a little more difficulty explaining the doctored passport.

In the fall of ‘99, bored with her life and her boyfriend, she called Dana, whom she’d met years earlier, and asked him for a job. Romance, she says, was not on her mind. “I knew all about Dana,” she says. “I didn’t want to be balanced between a supermodel and a movie star.” But Giacchetto pursued her with typical zeal and eventually won her over, though friends were surprised by his ardor. “Dana was like a child,” explains one, “always reaching for the shiniest object in the room, but Allegra wasn’t like that at all. She was always at his side, but never really engaged. She just seemed mesmerized by his life.”

Barely a month into the relationship, Giacchetto’s partners had tossed him out of the $100 million venture-capital firm they had started with Chase Manhattan; his best friend, agent Jay Moloney, had hung himself; the SEC had begun an investigation; and dozens of anxious clients were pressing him to return their money. Giacchetto seemed oddly detached from his growing woes. “We went on walks, we watched movies, he didn’t want to talk about business,” Brosco says. “We were too busy falling in love.”

But by the time she moved into his Prince Street loft in November, the situation had become too dire to ignore. She returned home one afternoon to find Dana sobbing uncontrollably on the phone with DiCaprio’s mother, begging her to persuade Leo not to leave him. (“Losing Leo was like losing a brother,” Allegra says.) The same month, the FBI launched an early-morning raid on his home and downstairs office, carting boxes of bills and documents while she watched in her nightgown. She was also there, alone, when the agents returned at 5 a.m. six weeks later with a warrant for Dana’s arrest. They spent twenty minutes searching the apartment for Giacchetto, who was flying back from a trip to Tokyo. Brosco picked him up that night at the airport, and he surrendered the next morning.

He was charged with looting upwards of $9 million in funds belonging to clients. Prosecutors claimed he was using investors’ funds as a personal slush pile, moving money in and out of various accounts to mask his losses and to finance his lavish lifestyle. He and his pals ran up an $80,000 bill on a weeklong stay at the Chateau Marmont. Another $12,000 went to help purchase a car for his sometime security guard and close friend, a handsome NYPD cop. With Dana’s help, some of his clients succeeded in getting back their money. Other clients, especially the less celebrated ones, were left holding the bag.

Giacchetto’s elderly parents paid his bail by mortgaging their house, but their son’s freedom was short-lived. On April 9, he violated terms of his release by flying without warning to Las Vegas. Brosco says he headed out West to “clear his head and make a few deals.” He returned clutching a briefcase stuffed with 80 first-class airline tickets, $4,000 in small bills, and a clumsily doctored passport that had long since expired. Drunk and incoherent, he was arrested and confined to an isolation cell at the Metropolitan Correctional Center, which he later described to friends as “the VIP room of jail.”

Giacchetto’s troubles filled Brosco with new purpose, and she devoted herself full-time to his redemption: helping him find a lawyer, raising money for his defense, calling up his old friends to plead for their support. She has not always been successful. “I couldn’t believe the gall,” says the recipient of one such call. “I told her I already gave at the office.”

Brosco is not unaware of the frustration she inspires. “Most people who read this will think I’m either desperate or crazy,” she admits matter-of-factly. It’s a frosty winter evening, and a shivering Brosco is nursing a vodka on the patio of a SoHo restaurant, where we have retreated to elude eavesdropping diners inside. Jobless for months after Dana’s arrest, she now lives with a roommate in a cramped one-bedroom on Cleveland Place and supports herself doing temp work.

Giacchetto is currently incarcerated in a dormitory at the Metropolitan Detention Center in downtown Brooklyn, the third facility he’s occupied since his arrest. He sleeps in a bunk bed in a room with about 200 other inmates, rises each morning at six, eats dinner at five, and must be in his bunk by eleven. To occupy his time, he reads, plays Scrabble, listens to the radio, and writes long poems to his fiancée and his prominent lawyer, Ronald Fischetti.

The once-plump moneyman works out three times a day, bulking up as he’s shed twenty pounds. As part of his “spiritual transformation,” says Brosco, he reads from the Gospels at services each Sunday and works the pay phone trying to make amends. Not long ago, she says, he waited in line nearly two hours to call Michael Ovitz, whose receptionist refused to take the call. He has also sent dozens of letters to former clients, asking for their help and forgiveness. Most have gone unanswered.

Early on, there were rumors that the high-profile, effete prisoner had been assaulted by other inmates, but Brosco denies this. “He just tries to keep to himself,” she says. Since his arrest, Giacchetto has declined all interview requests, including entreaties from Barbara Walters and 60 Minutes. But he still keeps up with his press. “He knows when he’s in the paper before I do,” says Brosco, who adds that Dana tries not to dwell on the past. Once, while strolling though the prison yard during a stint upstate in Otisville, Giacchetto spotted his old friend Johnny Depp, there to research a movie. “The old Dana would have fallen over himself to get to him,” says Brosco. The new Dana walked sheepishly the other way.

Brosco insists that hubris, not greed, caused Giacchetto’s downfall. “I’m not here to tell you he’s innocent. I’m not stupid,” she says. “Dana pleaded guilty. He’s sorry. He knows he fucked up, and so do I. But money was never his god. He could be a sycophant and a star-fucker, so desperate not to disappoint anybody that when things got bad, he took money out of his own account to pay people off. When Dana invested in Iridium and Iridium went bad, his clients came to him and said, ‘Give me my money back.’ And the dumb-ass, instead of saying, You know what? I fucked up, it was a bad investment, he paid them back!”

The problems at Cassandra were exacerbated, Brosco admits, by Dana’s frenetic socializing: “Some nights we’d be hanging out quietly alone, it would be like four o’clock in the morning, and the doorbell would ring, and in would come fifteen people.” Drugs were an inevitable part of that scene, though Brosco claims Giacchetto’s taste ran to alcohol and tranquilizers rather than to club drugs or cocaine. “People were doing whatever their recreational drug was. And that was part of his demise. All the money and fame and partying made him lose his center.”

When he was first arrested, a few friends, like Alanis Morissette, rallied around him. But his bizarre Las Vegas high jinks scared off even his most die-hard fans. At a subsequent bail hearing, Dana, cuffed and clad in his prison jumpsuit, tearfully denied he intended to flee, but Brosco claims his lawyer at the time, Andrew Levander, privately denounced him as a liar and asked to be let off the case. “He basically left him for dead,” she says bitterly. (“Under the canon of ethics,” Levander responds, “I cannot comment on my dealings with Mr. Giacchetto.”)

Brosco also claims that Giacchetto, who traveled constantly, always stockpiled airline tickets so he could have them readily on hand. (Others speculate that the onetime millionaire, chafing at his imposed $100-a-day allowance, hoped to trade in the tickets for $40,000 in cash.) She has a little more difficulty explaining the doctored passport. “The only speculation I can make is that he was fucked up drinking, taking prescription drugs, under unbelievable pressure, and he just cracked,” she says. “His parents, who aren’t wealthy, put up their house. Dana would never fuck them over like that. He would never have done that to me.

Prosecutors charged that Giacchetto planned to elope with Brosco to Italy, a scenario she doesn’t deny. “Dana called me and said, ‘I just bought two first-class tickets to Rome. Do you mind getting married in Rome?’ ” she recalls. “And I said, ‘Of course, I’d love to. But Dana, you have a bit of a passport problem.’ And he started to laugh and he said, ‘I know. But isn’t it a snug idea?’ Snug was Dana’s word for everything that’s loving. So I said yes. I mean, I’m not going to say, ‘No, you fucking moron; it’s a stupid idea! Now everyone’s going to think you were trying to flee the country with me.’ I said, ‘Yeah, it’s a lovely idea; yup, very snug.’ But it was just a fantasy.

“I know some people think, Oh, Allegra’s this dumb woman who’s been manipulated by Dana’s charm and his exaggeration,” she continues, dragging deeply on her umpteenth cigarette. “And the truth is, he’s definitely prone to hyperbole. But no one in a million years will ever occupy the place this man occupies in my life.”

Siacchetto’s SoHo loft was vacated in July; his penchant for partying provoked the building into evicting him long before his legal problems arose. His possessions were stored or put up for sale. First to go were Giacchetto’s paintings – some 40 Bleckners, George Condos, and Lichtensteins valued in the millions. Last November, in an attempt to fend off an imminent lawsuit, Giacchetto turned the works over to the rock group Phish, the earliest of his clients to charge malfeasance.

Next to go were his endlessly photographed cockatoos. Beloved by Giacchetto, the birds despised each other, and they were dispersed to different coasts. Angel, the female, now lives in Brooklyn with Giacchetto’s former maid. The male, Tiberius, was adopted by a cousin in Los Angeles. Brosco packed the rest of Dana’s belongings into boxes – and spent weeks rummaging through the detritus of his life. “It seemed like he had a good time,” she admits. “He saved every VIP pass he got.”

She took special care with his suits – racks of Helmut Langs and Pradas, which she carefully folded and packed away. Giacchetto’s belongings are now in storage in Massachusetts, where they may be confiscated to pay off his fines.

The night before she moved out, Brosco slept alone on a sheet in the middle of the now-empty loft. The electricity had been shut off earlier in the day. By then, there were dozens of mice running around the apartment, some climbing into her makeshift bed. “It was like the apocalypse,” she says. “The mice started coming a few weeks after Dana was in jail. I hired an exterminator, but it didn’t do any good. By the end, there were about twenty of them and they were everywhere. It was almost like they knew Dana was gone.”

Postscript: Dana Does Detention