Even when the man they called "Jimmy Henchman" was on trial earlier this month for running a cocaine ring, his ties to the feud that led to the murders of two hip-hop legends preceded him.
On Friday, Manhattan officials charged James Rosemond with arranging the murder of an associate of the rapper 50 Cent.
On June 5, Rosemond was convicted in a Brooklyn federal court of peddling millions of dollars worth of cocaine.
Rosemond, 47, was indicted for conspiring with five other men to kill the associate, Lowell Fletcher, in 2009.
"This has not been a good month for Jimmy the Henchman," Raymond W. Kelly, the New York police commissioner, said in a statement.
Rosemond's lawyer, Gerald L. Shargel, did not immediately respond to requests for comment.
Rosemond is notorious in the hip-hop community for his alleged involvement — which he has consistently denied — in the bicoastal feud that led to the murders of rappers Tupac Shakur and Christopher Wallace, known as Biggie Smalls.
He served as the CEO of Czar Entertainment which managed big-name artists including the Game, 50 Cent, Akon, Brandy and boxer Mike Tyson.