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by Steven Barboza

Former rap mogul and emperor of bling Damon Dash may soon have a new moniker: turnaround king.

The question on the minds of hip hop cognoscenti, the glitterati and reporters alike is whether Dash, who co-founded the twin cash cows of rap music and fashion, Roc-A-Fella Records and Rocawear, will earn the dubious distinction of actually living a “hard knock life” after having earned a fortune for producing a smash record of the same name.

The mogul, once one of the ten richest and most powerful men in hip-hop, is now reportedly broke. He lost his home, and a Manhattan judge even ordered the city to seize his SUV because he couldn’t afford his monthly car note.

However, some observers vouch for his ability to stage a comeback. “At the end of the day, he’s an entrepreneur,” says Lola Ogunnaike, a journalist who wrote for Vibe and Rolling Stone magazines and who was the top culture reporter for The New York Times. “He’s not necessarily a music man; he’s a businessman, and wherever there’s a check to be made, he’s going to look into it.”

The high point of his success is traced to 1994, when he met Shawn Carter, a former drug dealer from Brooklyn who wanted to become a rapper.  Dash put up his own money for Carter’s first recordings, pressed discs himself and sold them out of his car, launching Roc-A-Fella and the career of the future rap star who would come to be known as Jay-Z.

Two years later, Dash produced the artist’s debut album, “Reasonable Doubt,” and was credited with putting the upscale “varnish” on Jay-Z’s appeal. Under Dash’s managerial skill, Jay-Z recorded nine No. 1 albums and won four Grammys.

In the music industry, you’re really only one hit, one act away from a comeback. So anything is possible,” says Ogunnaike, a former entertainment correspondent for CNN’s flagship morning news program, American Morning. “The Jay-Zs of the world only come around every so often, but if he were to discover the next Jay-Z, I think Damon Dash would be at the top of everyone’s invite list. The name Damon Dash would be on the tip of everyone’s tongue again.”

Many hip-hop observers credit Dash for pioneering the financial deals upon which rap music thrives.  And his current deals could earn him millions more, not just in music, but in communications and even the auto industry.

Dash, 38, has a history of overcoming great adversity. He grew up in a rough Harlem neighborhood. His mother died of an asthma attack when he was 15, and he proved resourceful enough to put himself through a series of boarding schools. He then built a business out of throwing parties at Harlem’s Cotton Club, which he rented out.

He went on to become a major architect of the current music scene, reaping millions of dollars for grooming and launching artists who would become rap royalty, including of course, the genre’s reigning superstar, Jay-Z, who counts President Barack Obama as a fan.

He brought vision to the music business. Some even say Jay-Z’s suave public persona was molded in Dash’s imagination.

“I think it’s important to keep in mind that Damon Dash went to private schools,” Ogunnaike explains.  “So he has been used to rubbing shoulders with the elite for a long time. So I think he just had a more sophisticated world view, and his world just wasn’t as narrow as somebody like Jay-Z, who grew up in the Marcy Projects. So I do think he introduced Jay-Z to a certain level of sophistication, made him a little more worldly, a little more cultured. But anyone who knows Jay-Z knows that he is a quick study. And soon enough the student was right up there with sensei.”

Dash, who also launched the careers of Kanye West, Beanie Sigel, Cam’ron and other stars, brought ruthless negotiating skills to the deal-making table. Offered lucrative contracts with major record companies, he held out for even bigger paydays.  In the end, he revolutionized the business of rap by insisting his artists receive equity for their labors, rather than settling for the work-for-hire arrangements traditionally offered to black recording artists.

Dash profited handsomely, using his earnings to branch out with spin-off ventures. By age 35, he owned a record label, five clothing and shoe companies, a Swiss watch company, a top-shelf vodka company, a television production house, and a movie production company. He estimated his worth at $50 million.

His business deals and lifestyle of conspicuous consumption were detailed in a 2006 profile in New York magazine. He wore a four-carat yellow-lemon diamond on his earlobe. He was driven around town in a $400,000 Maybach, employed a corps of butlers, cooks, photographers and personal assistants, owned 1,300 pairs of sneakers, and devoted the top floor of one of his homes to his clothes. The dressing room and the sneaker room each had their own bathroom.

“Dash had a reputation for being an aggressive negotiator, and also for being a bit of a hothead,” Ogunnaike says. “Now that worked to Jay-Z’s benefit because Damon Dash essentially played bad cop and Jay-Z was allowed to play good cop, and that worked when they were on the same team. But eventually it started affecting business, because some people found Damon Dash impossible to work with, and some found his temper to be over the top and his behavior to be unprofessional.”

Dash’s fall has been spectacular – and public. A decade after the two had met, Jay-Z broke his business ties to Dash. In 2004, when Def Jam, which owned a 50% stake in Roc-A-Fella, purchased the remaining stake, Jay-Z was named president, a job some think should have gone to Dash. The following year, Jay-Z purchased Dash’s stake in Rocawear for $20 million.

Since then, Jay-Z has parlayed his fortune into the hundreds of millions of dollars, while Dash is reportedly broke.  Earlier this year,  he owed $2 million in state taxes. Eastern Savings Bank started foreclosure proceedings on his two New York condominiums. He was sued by law firms and landlords for unpaid bills, and in 2008, a Manhattan judge ordered the city to seize his Chevrolet Tahoe SUV when he couldn’t come up with the $714.99 monthly payment.

A year ago, his wife, fashion designer Rachel Roy, the glamorous Indian-Dutch mother of two of his children, filed for divorce, seeking “non-monetary relief.” The move came within a year after Roy and Dash signed a joint venture deal with Jones Apparel Group to develop, market and license the New York-based brand.

Some believe only Dash can blaze a new trail in music, because the current crop of recording executives lack his vision and hunger for a path-breaking deal. “I like to be the brokest guy in the room. That inspires me,” he reportedly told New York magazine. “I rubbed two sticks together and made money.”

He has a history of surprisingly bold moves; some might say too bold. Earlier in the decade, after he bought the sneaker company Pro-Keds and repositioned it as a hip-hop brand, he introduced a line of sneakers with lemon- and watermelon-scented soles. The line proved to be a hip hop flop.

His newest deals, however, are mainstream and may be innovative enough to earn him piles of money. In September he announced plans to launch a radio station called Magnet Radio. It will feature less advertising than is customary on radio, creating a new business model, he said.

He also moved into the car business with the Tiret Sport Coupe. Said to be based on the Range Rover Sport, the luxury two-door SUV was unveiled in September in Switzerland alongside Tiret’s opulent bejeweled timepieces.

Dash says he learned to hustle from his mother, a secretary who sold clothes on the side out of their apartment and who sometimes offered fashions not yet available in stores. Success in his latest business ventures will go a long way toward proving how well he learned the basics of hustling – and whether he will break new ground as hip hop’s first turnaround wizard.

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