Dancehall artiste Squash will finally learn his fate on November 24, 2025, when he returns to U.S. federal court for sentencing on a firearm-related charge that could determine the course of his career. The “6ix Boss,” born Andrae Maurice Whittaker, pleaded guilty earlier this month to being an illegal alien in possession of a firearm. While prosecutors have recommended a reduced sentence that could see him serve fewer than five years, the ultimate decision rests solely with the judge — and the possibility of a much harsher penalty still looms.
The case stems from a February 24 traffic stop in Miami Beach, where federal agents had been monitoring Squash on suspicion of leading a transnational gang. According to court filings, he was spotted accepting what appeared to be a firearm before entering a vehicle that later committed several traffic violations. When the car was pulled over, authorities discovered a loaded Glock 19 in the glove compartment, and Squash was observed reaching toward it. A second weapon was also seized during the stop, strengthening the case against him.
In exchange for his guilty plea, prosecutors dropped a more serious count of unlawful possession of an automatic weapon and offered the entertainer a potential break under the federal sentencing guidelines. His plea placed him at point 17, translating to a recommended sentencing range of 24 to 63 months. However, under federal regulations, he would be required to serve at least 85 percent of whatever term is handed down. Importantly, the court stressed that the agreement does not bind the judge, who could still impose the maximum penalty of 15 years in prison, three years of supervised release, and a US$250,000 fine.
Squash’s legal troubles stretch back to his immigration status. Court documents revealed that he entered the U.S. illegally in January 2021 after his visa was revoked two years earlier. By admitting guilt, he not only faces potential prison time but also the very real prospect of immediate deportation once his sentence is complete. “This conviction is a deportable offence,” the plea agreement noted, underlining the double blow that could await the Montego Bay native.
For fans of the 6ix Boss, the November sentencing represents both the end of one chapter and the uncertainty of another. Whether Squash serves a reduced term, the full weight of the law, or faces deportation, his future as a dancehall act hangs in the balance. The dancehall community — in Jamaica and abroad — now waits anxiously for the final ruling that could redefine the trajectory of one of its most interesting figures.
