Why Did Shyne Go To Prison? Revisiting The Case Involving Diddy

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(Photo by Samir Hussein/Getty Images for Sean Diddy Combs)
Unpacking Shyne and Diddy's involvement in a 1999 shooting that changed the trajectory of Shynes career forever.

Thanks to recent developments in the news, Diddy has been under a great deal of scrutiny. Many hip-hop heads are looking back into the history of the Bad Boy Records founder with a fresh set of eyes. One major moment in Diddy's story that has gone back under the microscope is his connection with the decade-long incarceration of former Bad Boy signee Shyne. In 1998, Shyne, a major up-and-comer in hip-hop, signed with the label. However, his career took a significant hit in 1999 after a shooting incident. In 2001, authorities charged and imprisoned Shyne, only three years after he signed the multi-million dollar deal. Diddy and Shyne faced charges, but the label mogul was mysteriously acquitted. Let's look at the incident and incarceration of Shyne and how it connects with Diddy in light of recent events.

The Shooting Occurred In December 1999

Just one year after joining Bad Boy, Shyne found himself embroiled in a shooting incident alongside Diddy and Jennifer Lopez. Diddy and Lopez maintained a romantic relationship during that time, and the trio attended an industry event at a New York nightclub. According to witness testimony, a man named Matthew Allen, who went by the nickname Scar, entered into a verbal altercation with Diddy. This soon escalated into a series of death threats and physical violence. Guns were drawn, and shots were fired inside of the packed night club, injuring three random bystanders. Prosecutors accused Shyne and Diddy of drawing guns in the building, though both rappers claimed to be acting in self-defense.

Shyne claimed he fired into the air, assuring the court that he did not hit any bystanders. Despite eyewitnesses' statements contradicting Shyne's claim and asserting that all three injured civilians sustained gunshot wounds from Shyne's gun, testimony from a ballistics expert appeared to challenge his assertion. The expert revealed that one of the injuries resulted from a 40-caliber weapon stock, which did not match Shyne's 9-millimeter weapon. Nevertheless, despite this evidence, the court convicted Shyne of two counts of assault and reckless endangerment. He was also tacked with criminal possession of an illegal weapon. Consequently, he received a ten-year prison sentence with no possibility of parole.

Diddy Was Acquitted Of All Charges

Despite Shyne's conviction, Diddy managed to wriggle his way out of numerous charges associated with that fateful evening. Diddy's charges included attempted murder, intentional assault in the first degree, illegal possession of two firearms, and bribery in connection with the impending trial. Once Shyne was incarcerated in Clinton Correctional Facility, he severed all ties with Diddy and Bad Boy Records. He has since expressed feeling extremely bitter to his former label boss. The details surrounding Diddy's acquittal are murky. Yet, many rap fans assume the executive and his lawyers conspired to pin the entire shooting on his signee.

Shyne Has Since Made Up With Diddy

Despite their past conflicts, Shyne and Diddy eventually reconciled after authorities released the former rapper from prison and deported him to his home country of Belize. Since his sentencing, Shyne has converted to Orthodox Judaism, reunited with his estranged father, and actively served his constituents after they elected him as Leader of the Opposition in the Belize House of Representatives. Shortly after joining the House of Representatives, government officials across Belize called for an amendment that would bar ex-convicts such as Shyne from running for office. This injustice caused Diddy to reach out in support of his former collaborator, and the two made peace.

In a January 2022 interview with Drink Champs, Shyne expressed, "Puff, to me, totally redeemed himself" in response to Diddy's political support. He continued, "I did go through a stage of bitterness. But in retrospect, I blame it more on the lawyers that were advising [Diddy.]... That was over a decade ago and I was in a different space then.”

About The Author
TeeJay Small is a professional humorist, pop culture columnist, and an avid enjoyer of all things hip hop. When he's not compiling dozens of monologue-style jokes about the most absurd news headlines, or furiously scribbling rewrites for his television pilot, you can find him carefully analyzing the lyrics to the latest Griselda or Dreamville releases, or digging in the crates to find the hottest up-and-coming rappers. After receiving his bachelor's degree in English/Communications from UMASS Boston, TeeJay set out on a journey to travel the world and develop a culturally diverse media career. He has been personally assured by both members of EARTHGANG that he is, in fact, part of the culture.