When Does Roc Nation Rapper Casanova Get Out of Prison? Here's What We Know

The Breakdown: Casanova signed to Roc Nation after the success of his 2016 song “Don’t Run." His 2018 album Commissary featured artists like Chris Brown, Mozzy, and Fabolous. The project reflected his former time in prison, and street life caught up with him again in 2023.

Casanova has become known as one of the rawest voices coming out of New York. His songs “Set Tripping” and “Don’t Run” captured the energy of the NYC streets. His success was led by street credibility and being signed with Jay-Z’s Roc Nation music label. He’s also had a history of beef with New York rapper Tekashi69 and his rival Trey Nine Gangsta Bloods gang, which resulted in a shooting without injury.

The rapper isn’t all bark, though. He’s shown his bite through the various legal troubles he’s had since the mid-2000s. The “Be Safe Tho” artist has dropped various projects and songs that exude his credibility to run the streets of New York. Now, it’s finally caught up to him and his affiliates to put them behind bars.

On June 27, 2023, Casanova was convicted of racketeering and narcotics offenses (per the U.S. Attorney’s Office). He was sentenced to 188 months, which comes out to 15 years and 8 months.

The rapper pleaded guilty to charges of racketeering conspiracy and marijuana trafficking in 2022. These charges were formed against him for a shooting in 2020, a robbery in 2018, and trafficking over 100 kilograms of marijuana. Casanova is currently looking to be a free man again in 2038, assuming his sentence isn’t extended.

Casanova, born Caswell Senior, surrendered to authorities in December 2020 on RICO charges. The 34-year-old rapper was charged alongside 17 other members of the Untouchable Gorilla Stone Nation gang. The gang had been highlighted as a threat to the state of New York and New York City for some time before the arrests were officially made.

Casanova was on trial with Gorilla Stone leader Dwight Reid, known as “Dick Wolf”. Under Reid’s leadership, the gang was revered as one of the most organized and violent crime syndicates in the state of New York. The other members put on trial were charged with multiple offenses, including racketeering, various frauds, attempted murder, and acts of violence that included the murder of a 15-year-old in Poughkeepsie.

While Reid acted as the ringleader of the gang, the Roc Nation artist was also seen as a leader and charged as such. Casanova may not have had a direct hand in some of the crimes committed, but he was seen as a key figure in organizing the crimes from a higher position within Gorilla Stone. However, this isn’t the rapper’s first run-in with trouble.

He served seven years in a New York prison after being indicted for robbery in 2006. During his time served there, he befriended hip-hop podcaster Taxstone and found security and reputation with Bloods, specifically Untouchable Gorilla Stone Nation. Once he was out in 2013, he claimed he wanted to turn his life around but struggled to find legal work.

The connections he’d made in prison led to him continuing to have ties with the gang. Even while pursuing his rap career, Casanova held close relationships with various gang members, including Reid. The rapper was found to have direct involvement in the 2020 Florida shooting, as well as the 2018 robbery in NYC.

According to the Associated Press, the Brooklyn-born rapper was removed from the lineup of a hip-hop festival in 2019. The NYPD requested the removal, stating that it would raise safety concerns if he and four others, including the late Pop Smoke, took the stage. When the indictments were made, it was found that the gang had at least five phones wiretapped to gain information.

Casanova has posted photos and even lost permission for virtual visits while in prison. There’s no evidence that the rapper will get out earlier than the 15 years he was sentenced to, but he may get out sooner due to his cooperation with authorities in the case.