Dancehall’s 6ix Boss could be a free man sooner than expected. According to the Federal Bureau of Prisons, Montego Bay deejay Andrae “Squash” Whittaker is provisionally scheduled for release from U.S. custody on January 25, 2027, nearly a year earlier than many fans anticipated. However, the possibility of deportation proceedings could still derail his plans once he walks free, with legal experts suggesting that the U.S. immigration authorities may move swiftly following his release.
Squash was sentenced in November 2025 to two years and three months in federal prison after pleading guilty in a Miami court to possessing a firearm while living illegally in the United States. The case stemmed from a February traffic stop in which police recovered a modified Glock 19 from a vehicle he was travelling in. Prosecutors cited the weapon’s illegal modification as a key factor, while his legal team rejected claims that the artiste was involved in any organised criminal activity, describing that narrative as exaggerated and unproven.
The sentencing unfolded against a backdrop of vocal support from the dancehall fraternity, most notably Vybz Kartel. On the eve of the hearing, Kartel publicly backed the young deejay, urging fans to believe in personal change and redemption. The message resonated widely, reinforcing Squash’s standing within the culture and highlighting the genre’s long-standing conversations around hardship, survival, and second chances.
Now, with a release date on the horizon, attention is shifting to what the future holds. Squash, known for gritty street anthems like Big Breeze and Shub Out, is expected to face removal proceedings almost immediately after completing his sentence. Whether deported or granted limited relief, his next chapter appears set to unfold outside the U.S., with fans watching closely to see how the experience reshapes both his life and his music.
