Squash’s Plea Deal Revealed: One Charge Dropped, Faces Up to 15 Years and Possible $250K Fine; Sentencing Pending

Dancehall artiste Squash has officially struck a deal with U.S. prosecutors, pleading guilty to one federal gun charge in exchange for a lighter outcome and the dismissal of a second, more serious count. The Montego Bay native, born Andrae Maurice Whittaker, admitted in court on Friday to being an illegal alien in possession of a firearm or ammunition—a charge that carries up to 15 years in prison, three years of supervised release, and a possible fine of US$250,000. While prosecutors have agreed to recommend a reduced sentence, the court emphasised that the final decision rests entirely with the judge.

As part of the agreement, the second charge of unlawful possession of an automatic weapon has been dropped, sparing Squash from potentially harsher penalties. The artiste must also pay a US$100 special assessment fee and forfeit any other firearms or ammunition in his possession. Importantly, he acknowledged that this conviction is a deportable offence, meaning his plea could trigger automatic removal from the United States once sentencing concludes.

The plea deal also comes with strict conditions: Squash cannot withdraw his plea if the court ignores the prosecution’s sentencing recommendation, and the agreement becomes void if he lies, withholds information, commits another crime, or attempts to misrepresent government officials. By accepting the deal, he also agreed not to contest several key facts. According to court filings, on February 24, 2025, while under surveillance in Miami Beach, he was seen accepting what appeared to be a firearm before entering a vehicle that committed multiple traffic violations. When police stopped the car, Squash was observed reaching for the glove compartment, where a loaded Glock 19 pistol was later found.

Court documents further revealed that Squash entered the U.S. illegally in January 2021 after his visa was revoked in 2019. He knowingly possessed the loaded Glock while residing in the country without legal permission. Although prosecutors have praised his decision to plead guilty as saving the court’s time and resources, sentencing remains at the court’s discretion, leaving the entertainer’s future uncertain.

For fans of the 6ix Boss, the guilty plea closes one chapter of a turbulent saga but opens another with even higher stakes: the looming decision on whether he will serve time behind bars in the U.S., be deported, or face both outcomes. With sentencing still to be scheduled, the dancehall community waits anxiously to see what’s next for one of its most controversial figures.