From Music Mogul to Convicted Criminal: Who Is Jimmy Henchman?

James Rosemond, better known in the entertainment world as Jimmy Henchman, once stood among hip-hop’s most influential and enigmatic figures. A Brooklyn-bred music executive, entrepreneur, and activist, Rosemond climbed from the rough streets of Flatbush to rub shoulders with industry giants, athletes, and political leaders. But what began as an inspiring come-up story quickly spiraled into one of the most cautionary tales in hip-hop history—darkened by drug trafficking, violence, and one of rap’s most notorious unsolved mysteries.

Born in 1965 in Harlem, Rosemond was raised by a single mother after his parents’ divorce. Determined to make something of himself, he leaned into New York City’s cultural ecosystem and quickly earned a reputation as a connector. In 1992, he co-founded the "How Can I Be Down" music conference—an event that became a launchpad for new talent and a networking hub for rising executives.

His vision extended beyond music. In 2002, Rosemond helped negotiate the Lennox Lewis vs. Mike Tyson heavyweight boxing match, securing a deal that split the purse evenly after one million pay-per-view buys—a testament to his negotiation savvy and reach.

Through his company Henchmen Entertainment, later renamed Czar Entertainment, Rosemond built a powerhouse management roster including The Game, Brandy, and Sean Kingston. He moved through the industry with calculated finesse, often aligning himself with social justice causes. Alongside Russell Simmons, he lobbied for the reform of New York’s Rockefeller Drug Laws, positioning himself as both businessman and activist.

But behind the executive polish lay darker chapters.

In one of hip-hop’s most explosive revelations, Rosemond allegedly confessed during a 2011 proffer session—a legal negotiation in which statements are protected from prosecution—that he played a role in the 1994 ambush and shooting of Tupac Shakur at Quad Studios in New York.

According to journalist Chuck Philips of the Village Voice, court filings referred to the “defendant’s own admission,” though no official transcript has ever been released. The incident left Tupac shot five times and robbed, deepening the East Coast vs. West Coast beef that would later claim the lives of both Tupac Shakur and The Notorious B.I.G.

Tupac had long suspected Rosemond's involvement, famously calling him out by name on his track "Against All Odds":

“And did I mention / Promised a payback, Jimmy Henchman?”

The alleged confession further clouded Rosemond’s legacy and permanently tethered him to one of rap’s darkest turning points.

In 2010, Rosemond’s empire began to unravel. He was arrested and charged with running a multimillion-dollar cocaine distribution network, using music industry ties to funnel drugs coast to coast. Charges included money laundering, witness tampering, and intimidation. In 2012, he was convicted and sentenced to life in prison.

But the legal trouble didn’t stop there.

In a separate case, Rosemond was convicted of orchestrating the murder of Lowell “Lodi Mack” Fletcher, an associate of rapper 50 Cent. The hit was allegedly payback for a previous assault on Rosemond’s son. After multiple trials, he was handed a second life sentence—this time for murder-for-hire.

The duality of Jimmy Henchman continues to spark debate. Was he a visionary entrepreneur and community advocate who was unfairly targeted, or a power-hungry kingpin who blurred the lines between legitimate business and street crime?

At one point, he stood as the embodiment of hip-hop’s rags-to-riches ethos: a man who rose from nothing to command influence in music, sports, and politics. But the very ambition that fueled his rise may have hastened his fall—alongside a desire for respect and control in both boardrooms and the streets.

Now serving multiple life sentences, James “Jimmy Henchman” Rosemond’s name remains divisive. Some regard him as a fallen mogul, others as a cautionary tale. But no one can deny his impact on hip-hop culture—and the high price of power pursued without limits.

In the ever-evolving story of hip-hop, Henchman's tale is a stark reminder: no matter how high you rise, the past always catches up.