happier times.

Damon Dash has got 99 problems, plus one. The man who once presided over a hip hop empire valued at $50 million, is officially broke. And soon to be lonely.

Dash, who in 2005 sold his stake in Rocawear to Jay-Z for $20 million, owes $2 million in state taxes. The men have since split ways as both friends and business partners. Also, Eastern Savings Bank has started foreclosure proceedings on Dash and his wife’s two luxury Tribeca condos (of which a lawsuit filed in August claimed they had had unpaid mortgage debts totaling $7.3 million). And, last year, a Manhattan judge ordered the city to seize his Chevrolet Tahoe SUV because he didn’t make his $714.99 monthly payment.

Now, his wife, designer Rachel Roy, has slapped the the man who co-founded Roc-a-Fella records, discovered Kanye West, and has production credits in both theater and film, with divorce papers. Dash met Roy while the she was working at Rocawear and helped launch her eponymous clothing line, of which he is still part owner. They married in Mexico in January 2005 and have two daughters.

Not that this softens the blow, but Roy, clearly aware of his financial woes and attempting to not completely kick him while he’s down, claims the divorce is for “nonmonetary relief.”

-Danielle Cheesman