Dancehall entertainer Squash is set to walk free from a U.S. federal prison on January 25, 2027, according to the Federal Bureau of Prisons. The St James-born DJ has been serving a 27-month sentence after being convicted in November last year on gun-related charges.
The charges followed a February 2025 traffic stop incident in which Squash was reportedly found with firearms in the vehicle he and an associate occupied. The pair were pulled over in Miami, and police said they found two Glock pistols while searching the vehicle. Among the firearms was a modified one with an invisi-switch plate, which is sometimes referred to in Jamaica as a “chip Glock”. The pair was arrested, and federal authorities took over the case.
Squash, legally named Andrae Whittaker, faced charges for being an alien in possession of a firearm and unlawful possession of a machine gun. Squash was presented with a plea deal and, although he initially planned to fight the charges in court, he accepted. After pleading guilty to being an alien in possession of a firearm, he was sentenced to 27 months in prison on November 24.
Federal sentencing rules typically release inmates with good behaviour after serving about 80 per cent of their term, which means Squash’s January 2027 release aligns with standard procedures. While he will be released from prison, his legal troubles have not ended since the crime is considered a deportable offence.
Under the terms of his plea agreement, admitting to the firearm charge as a non-citizen makes Squash subject to deportation. Even though he is married to an American citizen, U.S. immigration authorities are expected to begin removal proceedings once he is released.
Squash is not the only member of his family encountering immigration issues. His father is also facing deportation after he was taken into custody by U.S. Immigration and Customs Enforcement (ICE) in September 2025. Additionally, Chronic Law, who is a member of Squash’s Sixx camp, is being held at one of ICE’s detention centres.