Earlier this week, music mogul and real life O.G. James “Jimmy Henchman” Rosemond was found guilty on 13 charges for allegedly being the leader of the “Rosemond Organization,” a group that supposedly moved hundreds of kilos a week.
For years, Jimmy Henchman’s name rang loudly in hip-hop circles. Recently, he was the manager of notable rappers and artists like Game, Gucci Mane, Brandy, Sean Kingston, Sheek Louch and Akon.
But before that, the Haitian-native was a notorious street guy from New York City, who reached infamy after Tupac rapped that he was going to “payback, Jimmy Henchman,” because Pac felt like he was one of the people who set him up and shot him back at Quads studio in 1994.
It was never confirmed that Henchman had a role in Pac’s shooting, but in 2008, the LA Times printed a story by Chuck Phillips which pointed a finger at Henchman as the man responsible for the shooting.
The story was later retracted after TheSmokingSection revealed some of the documents used as evidence weren’t real.
Henchman is just one street guy who is also known for his rap connects. Click through our list and check out seven other gangstas with music ties!
Big Meech & Young Jeezy
For over 20 years, Demetrius “Big Meech” Flenory and his brother Terry “Southwest T” Flenory were the leaders of a multi-million dollar drug organization empire called BMF (which stands for Black Mafia Family.)
The duo, who were originally from Detroit, made their second home in Atlanta. In the mid-2000s, Big Meech was trying to get a foot in the rap game, so BMF launched a record label. They collaborated with Atlanta rapper Young Jeezy, who had a heavy buzz from his Streets is Watching mixtape, on numerous occasions.
Big Meech and hundreds of his crewmembers were eventually arrested, and in 2007, Demetrius took a plea. He was sentenced to 30 years in federal prison.
In 2010, Young Jeezy famously took offense to Rick Ross’ ode to the criminal organization, “B.M.F. (Blowin’ Money Fast),” claiming that Ross didn’t know the crew.
Chaz “Slim” Williams & 50 Cent
Chaz “Slim” Williams was one of the most notorious bank robbers during the late ’60s and throughout the ’70s. One of his most famous occurrences happened when he actually robbed a bank while serving time in a federal Michigan prison.
In the ’90s and the 2000s he started to promote parties and rubbed shoulders with the likes of DMX, Jay-Z and Ja Rule.
He was also, at one point, 50 Cent’s manager. However, things got ugly between the two and 50 claimed that Chaz had something to do with his famous 2000 shooting, where he was hit nine times.
In the song “Many Men,” 50 Cent had the lyric: “Slim switched sides on me, let n*ggas ride on me. I thought we was cool, why you want me to die homie?”
Kenneth “Supreme” McGriff, 50 Cent & Murder Inc.
Supreme and his nephew Gerald “Prince” Miller were the leaders of the Supreme Team, a Queens-based gang that sold truckloads of cocaine throughout the ’80s and parts of the ’90s.
When Irv Gotti, Ja Rule and their Murder Inc. crew were coming up in the rap game, Supreme was one of the people the rappers hung out with and shouted out in various songs.
Their association led to a federal investigation in 2003, claiming that Irv started his label using some of Preme’s drug money. The FEDs didn’t have enough evidence and Irv and his label were eventually found not guilty in court.
In 2007, Preme was convicted of murder-for-hire, on charges that he paid $50,000 to have rapper/drug dealer Eric “E-Money Bags” Smith and “Big Nose” Troy Singleton killed.
Preme seemed to play a part in the beef between 50 Cent and Murder Inc. 50 and Preme have some kind of past together, with 50 even shouting the crew out in his 1999 song “Ghetto Qur’an (Forgive Me)”: Yo, when you hear talk of the Southside, you hear talk of the team. See, ni*gas feared Prince and respected Preme. For all you slow muthaf*ckas Ima break it down iller, see Preme was a business man and Prince was the killer.”
E–Money Bags, Nas, Mobb Deep & Capone-N-Noreaga
E-Money Bags was a street guy who was trying to transition his way into the rap game. E-Money Bags released one official album, E-Moneybags We Trust, which had verses from all of Queen’s finest rappers at the time, including Nas, Capone-N-Noreaga and Kool G. Rap.
E-Money Bags also had a stake in the Queensbridge vs. Jay-Z beef. E-Money Bags famously got in a argument with Jay-Z on Hot 97 after Hov started introducing a rapper named H-Money Bags.
Things ended tragically for Bags in 2001, when he was killed, reportedly by a Supreme-associate.
Calvin “Klein” Bacote, Jay-Z & Akon
Calvin “Klein” Bacote was a drug dealer from Brooklyn who apparently did dirt with Jay-Z back in the late ’80s and early ’90s. According to Klein, him and Jay caught a case together back in ’89, where the kingpin took the brunt of the charges.
In the mid-90s Calvin got arrested for various drug charges, and he did 13 years in prison.
Calvin came home in the mid 2000, however, he felt like Jay didn’t support him enough financially, so he started a campaign discrediting the rapper’s drug dealer past.
Jay didn’t respond to the disses, but the legendary rapper did mention the drug dealer once in his The Black Album cut “Allure.” Calvin eventually found legal work as Akon’s road manager.
Anthony “Geezy” Gonzalez & the Clipse
Coming up, Anthony “Geez” Gonzalez was the Clipse’s manager and owner of a Virgina club called Encore Lounge. In 2010, the kingpin was sentenced to 32 years in prison after he admitted that he was the leader of a organization that made over $20 million dollars from drug sales.
Clipse didn’t help their friend by sending hints about their manager’s criminal history, which they did on their track “Feds Taking Pictures.” Pusha T raps “rumor has it there’s about eight figures in that ceiling.”
Charles “Chilly” Patton & Lupe Fiasco
Charles “Chilly” Patton is the co-founder of Lupe Fiasco’s 1/15 record label. In 2003, Chilly was charged with running a drug enterprise after he was busted with six kilos of heroin.
They found no official link to the drugs and Lupe, however, there was recorded conversations between the two where they talked about splitting up “whole yellow” and “whole red” ones. Lupe testified that they were talking about mixing music tracks, not drugs.
To this day, Lupe claims his partner is innocent.