Dancehall entertainer Squash is scheduled to walk free from a United States federal prison in early 2027, according to official records.
Information from the Federal Bureau of Prisons indicates that the St James–born artiste is set to be released from custody on January 25, 2027. Squash, whose real name is Andrae Whittaker, is currently serving a 27-month sentence handed down in November 2024.
The performer, popularly known as the Big Breeze DJ, was taken into custody following a traffic stop in Miami in February 2024. During a search of his vehicle, law enforcement officers reportedly found two Glock pistols, one of which had been altered with an invisi-switch plate—a modification commonly referred to in Jamaica as a “chip Glock.”
Federal authorities later assumed control of the case and charged Squash with being an alien in possession of a firearm and unlawful possession of a machine gun. Although he initially signaled an intention to contest the charges in court, the entertainer ultimately entered a plea agreement. He pleaded guilty to the firearm possession charge involving his immigration status.
On November 24, the court imposed a sentence of two years and three months behind bars. The projected January 2027 release date reflects roughly 80 per cent of the total sentence, a standard outcome in federal cases where inmates qualify for release based on good behaviour.
However, the artiste’s legal challenges may not end with his release. Squash is expected to face immigration removal proceedings after completing his prison term. Court documents note that his guilty plea constitutes a deportable offence, despite his marriage to a U.S. citizen.
Compounding matters, Squash’s father was detained by U.S. Immigration and Customs Enforcement (ICE) in September 2024 in connection with removal proceedings. Additionally, fellow Sixx camp member Chronic Law remains in the custody of U.S. immigration authorities.
As the release date approaches, the entertainer’s future in the United States remains uncertain.
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