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Dash was a star himself, challenging Diddy as the most visible hip-hop executive. He splashed champagne on girls in videos, dated the r&b singer Aaliyah, and reveled in his reputation as a pugnacious asshole in the boardroom. He now regards the Roc-a-Fella heyday with some regret: "I didn't really understand the ramifications of being so influential, of saying things that could potentially be negative," he says. "At the time, it was about getting money at any cost and talking about buying nice things that most people couldn't afford. I think it put a very superficial mentality into the world. If you're rapping about doing criminal things, the majority of your fans are criminals or fans of criminals." Whatever the merits of his social critique, Roc artists talked about it because they lived it: Sigel, for example, beat an attempted-murder rap in 2004 (although he served time on separate federal weapons charges), while Peedi Crakk did several stints in prison, most recently until April of this year.
If Roc-a-Fella really was injecting malevolent thoughts into the soft skulls of the impressionable, that brainwashing mercifully ended when the company was cleaved apart in 2004. Tension had been mounting for more than a year, starting when Dash appointed Cam'ron, a crony from Harlem, one of the label's vice presidents, while Jay-Z was vacationing in the Mediterranean. Eventually, Jay decided to sever business ties with his fellow founders; their stake in the company was sold back to Island Def Jam for a reported $10 million, while controlling interests in the remaining clothing, film, and alcohol ventures were sliced up. Jay signed a three-year contract to become president and CEO of Def Jam—a position he would leave in 2008 for Live Nation. He offered the rights to the name "Roc-a-Fella" to Dash and Biggs in exchange for the recording masters to Reasonable Doubt, but the pair wouldn't make the deal. "We all earned those masters," Dash says.
This turn of events remains bewildering. "The people that I was helping, once they realized their dreams, they did what a criminal would do," Dash continues. "They stabbed you in the back. Think about the frustration of building a brand for years that should be taking care of your family, and then the person that was the closest to you saying, 'Nah, you can't have no parts of it,' and flushing it."
It was the end of an era, both for East Coast rap and for a label whose artists and executives were once so close that they ate Sunday dinners with Jay-Z's family. Artists were divvied up, forced to pick sides. "I thought it was fucked up," says Leslie "Freeway" Pridgeon, a Philadelphia rapper who released his debut album on Roc-a-Fella in 2003. "I missed the whole family structure that we had: Dame, Jay, Biggs. It was more than just music, like we're riding regardless." The road had forked.
In 2006, Dash boasted to New York magazine that he was worth approximately $50 million. He and his wife owned a loft in Tribeca and a house in Beverly Hills. There was a personal chef and a $400,000 Maybach 62 with a driver. His closet housed 300 pairs of sneakers, with another 1,000 in storage. But Dash was a benevolent overlord: He wore a fresh T-shirt and pair of socks daily, then donated the once-worn items to charity. Whatever acrimony existed from the destruction of Roc-a-Fella was buried beneath heaps of money and a slew of entrepreneurial projects, including the Damon Dash Music Group, the Rachel Roy Designer Collection, Pro-Keds sneakers, Armandale vodka, America magazine, BlockSavvy Technology, an Apprentice-esque BET reality show called Ultimate Hustler, and excursions into the cinematic world.
But these new endeavors failed to benefit from the platinum touch Dash exhibited at Roc-a-Fella. A career as a boxing promoter—he partnered with former HBO executive Lou DiBella to form Dash-DiBella Boxing—fizzled. Despite a claim that his stable of fighters "all like to knock niggas the fuck out," none rose to champion ranks. Punches landed also at America, a glossy men's publication that folded shortly after the editor-in-chief filed a police report alleging Dash assaulted him. And although Dash had portrayed himself as an owner of Pro-Keds, the deal he struck in 2004 was only to license the name; he agreed to pay a monthly premium in order to build up the brand, with the stipulation that he would split the profits if the company later sold above its original value. Only problem: Pro-Keds was part of Stride-Rite, a publicly owned company. He was paying to promote a company in which he had no equity. "Bad deal on Dame Dash's part," Dash says now. "That's over."
The poor investments added up. By 2008, Dash owed New York State $2 million in taxes and faced lawsuits from lawyers and landlords. A bank began foreclosure proceedings on his Manhattan property; a judge ordered the seizure of his Chevy Tahoe. "No money, mo' problems" crowed the Daily News. Dash cut his losses, selling half his stake in the Rachel Roy Designer Collection to Jones Apparel Group. He claims the transaction as a victory, even if financially pyrrhic: "In a recession, I sold a company that had nothing to do with something I was perceived as knowing how to do," he says. "It's not about being famous, it's not about being rich. It's about having taste and style, and I was able to penetrate that, getting into the same circle as Anna Wintour, André Leon Talley. Instead of being best-dressed in Vibe, I was best-dressed in Vanity Fair." Still, as his business endeavors faltered, so did his marriage. In March 2009, his wife of four years—and mother of two of his children—filed for divorce. Dash won't discuss the current state of their relationship, but still refers to her as "my wife."