Shooting and trial (1999–2001) On December 27, 1999, Shyne, Sean Combs, and Combs' then-girlfriend, singer/actress
Jennifer Lopez, were present at a shooting at Club New York, a Manhattan nightclub in Times Square. The three of them were in attendance at a Manhattan nightclub named Club New York, on West 43rd Street in
Times Square. Prosecutors charged that after Allen's accomplice threw money at Combs, the two men and Shyne all drew guns. Soon after, three gunshots were fired in the packed nightclub. One injured witness, Natania Reuben, said she saw both Combs and Shyne shoot guns; Reuben was shot in the nose. Shyne was accused of firing three shots that wounded three people. He maintained that he had fired into the air, and did not believe that it was bullets from his gun that injured the bystanders. while Shyne's defense attorney was Murray Richman. At his trial, an eyewitness and a ballistics expert testified that the three injuries may have been caused not by Shyne, but by a second gunman. The ballistics expert said that at least one injury may have been caused by a
.40 caliber weapon, while Shyne had a
9 millimeter gun. 40-caliber shells were found on the floor. Combs had been arrested and charged with illegally having two 9-millimeter guns and with bribery but was acquitted of the charges at the trial. Combs' bodyguard, who had been charged with illegal possession of a gun and bribery, was also acquitted at the trial.
Conrad Tillard, then known as the "hip hop minister" Conrad Muhammad, said: "Shyne's mother and grandmother placed this young man in the care and custody of Sean "Puffy" Combs, who they believed was a responsible executive of a company. Puffy has the same responsibility as a teacher, as a coach. This boy, Shyne, was out with his idol on that fateful night. When I put my child in your hands, I don't expect him to end up dead or in jail." In the 2024 documentary
The Honorable Shyne, he expressed the belief that his defense attorney may have undermined his trial.
Incarceration and Judaism conversion (2001–09) Shyne began serving his sentence at the
maximum security prison Clinton Correctional Facility in
Dannemora, New York. His legal team requested for an appeal for a
suspended sentence, which ultimately failed. During his time, Shyne attempted to "spit" on Combs after the latter tried to offer him $50,000 in cash to "take the fall" for the 1999 incident. Barrow has said that from the age of 13, he began to identify as an Israelite, after learning that his great-grandmother was a descendant of the
Beta Israel, ancient
Ethiopian Jews. In March 2006, he legally changed his name to Moses Michael Levi Barrow. He had already been studying
Judaism at the time of his arrest. In prison, with
rabbis he became a practicing Jew, keeping
kosher, and celebrating the
Jewish Sabbath and
Jewish holidays. He and his lawyers argued that by the court allowing Shyne to make deals with record producers, it would enable him to pay a higher potential settlement to victims of the shooting, who were separately pursuing civil lawsuits against him. Despite his convictions, his incarceration drew many sympathizers, as well as the admiration of many in the hip hop community. His adherence to the
code of silence, which he referred to several times on his eponymous debut album, earned him a hardcore reputation in the prison community and on the streets. Even while incarcerated, he was visited by representatives of record labels who wanted to make deals. Describing his nine years of incarceration, Shyne said: The entire process was devastating.... ten hours of incarceration is ten hours too much. So, for a human being to be animalized for ten years, there is no quick fix to that.... It's like being shot by an assailant, and you are running away for your life. You didn't even realize you got shot in your leg because you are running on adrenaline. It's not until you get to a place of safety that you realize you have a hole in your leg, and you collapse.... When I came out I didn't even realize how wounded and devastated I was because I numbed myself to the pain and destruction that I suffered.
Release and deportation (2009) Shyne was transferred to
Rikers Island where he was held for a
parole hearing, and then to the
Woodbourne Correctional Facility, where he spent the last months of his incarceration. A Manhattan judge signed an order that would schedule Shyne for release on October 6, 2009. He had served more than 9 years of a 10-year sentence, on which no terms for post-release supervision had originally been placed. At the request of the
New York State Department of Correctional Services, a mandatory
probation period of at least two and half years was added to Shyne's sentence. Shyne and his attorney, Oscar Michelen, had hoped to avoid probation. On October 6, 2009, Shyne was released from New York state custody, but was immediately taken into federal custody. He was detained by
U.S. Immigration and Customs Enforcement at a "detention facility in
western New York state". One source indicated that the facility in question was the Buffalo Federal Detention Facility in
Batavia. According to his attorney, federal officials were reviewing the rapper's immigration status and making a determination on whether or not he would be deported to his native, Belize. Shyne had a permanent resident "
green card", and his mother was a U.S. citizen, but he (himself) had never become a
naturalized citizen. Shyne's uncle,
Michael Finnegan, said that the family had prepared for the rapper's potential return to Belize. He revealed that Shyne and his representatives had been expecting to be intercepted by ICE officials upon his release, and had directed members of his legal team to prepare the necessary documents in an effort to address the situation.
Dean Barrow, Belize's Prime Minister and Shyne's father, sent a petition to former New York state governor
David Paterson, asking him to pardon his son. In 2008, Paterson had pardoned rapper
Slick Rick who, in a similar situation, also faced deportation. Barrow said he had been assured that the governor received his letter and that his request was under consideration, but that he did not expect to have any influence in swaying the decision. His family enlisted the assistance of
Charles Ogletree, an attorney and
Harvard Law School professor, and part of Barack Obama's circle, in Shyne's attempt to forestall deportation and regain entry into the U.S. In October 2009, Finnegan said that all legal matters regarding Shyne's case had been turned over to Ogletree. After all unsuccessful attempts to combat deportation from the country after his prison release, Shyne was deported to Belize on October 28, 2009. Given that he was a convicted felon, the United States would not allow him back into the country. ==Post-deportation==