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.
Also read: Hip-Hop Mogul James Rosemond Convicted as a Cocaine Kingpin
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.