In the 1980’s, few people were more feared in Brooklyn than legendary street figure Jimmy Rosemond, aka “Jimmy Henchman,” or “Jimmy Ace.”

After serving time at Rikers Island as a youth, Jimmy made his play to go legitimate.

In 1991, Jimmy co-founded the first Hip-Hop Mega conference called How Can I Be Down. This groundbreaking event would go on to become the breeding ground for some of hip-hop most celebrated artists. Jimmy started Henchman Entertainment (later changed to Czar Entertainment) where he managed artists & athletes that included Groove Theory, Akon, The Game, Gucci Mane, Sean Kingston, Rick Ross, Shyne, actor Michael K. Williams, and boxer Mike Tyson. Jimmy also managed a team of up-and-coming music producers and under his tutelage, huge hits like Salt N Peppa’s record Shoop were birthed.

Success and money rolled in, putting Jimmy firmly at the top of his game – Jimmy had made it, he had fought back against his tough childhood to become a respectable businessman making millions of dollars a year.

However, even as Jimmy tried to outrun his “Henchman” past, he would be sucked into the notorious East Coast vs West Coast rap wars, and later the feud between 50 Cent and The Game.

These beefs would haunt Jimmy forever, shining the spotlight back on his nefarious past & drawing the attention of US Attorney Todd Kaminsky.

In June of 2011, Jimmy was arrested by DEA Agents and US Marshalls, after being on the run for months. Jimmy was charged in the Eastern District of New York with what is called “The Kingpin Statute.” This 13-count indictment alleged that Jimmy was the leader of a nationwide, drug organization that was using the cover of his Hip-Hop music business and recording studios to transport close to 30 kilos of cocaine a month. Many in the Hip-Hop community believed that this was the inevitable conclusion to the man and the myth.

So how on earth did this story of success and smart business savvy end up in a high profile criminal trial and a life sentence?

Was it even possible that Jimmy, one of the most recognizable figures in hip hop, could moonlight as a ruthless drug trafficker who ran a bi-coastal drug ring that distributed thousands of kilos of cocaine onto the streets of Brooklyn and Queens?

Most importantly, did Jimmy ever have a legitimate chance to outrun his past, or does that only happen in movies?

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