Squash To Be Released From U.S. Prison In 2027, But Deportation Looms
Montego Bay native Andrae “Squash” Whittaker could soon be feeling the Big Breeze of freedom.
According to the Federal Bureau of Prisons, the Dancehall star is provisionally scheduled for release from the Federal Detention Center in Miami on January 25, 2027.
The scheduled date reflects time credits for federal inmates who qualify for early release based on good behavior. However, his freedom in the United States will likely be short-lived; upon release, he is expected to face deportation proceedings, setting up a swift return to his old stomping grounds in Jamaica.
Squash was sentenced in November 2025 to two years and three months in federal prison. The sentence followed his guilty plea in a Miami court to a charge of possessing a firearm.
The charges stemmed from a February 2025 traffic stop where police recovered a modified Glock 19 from a vehicle in which the artist was a passenger.
During the proceedings, prosecutors stated that Squash’s spouse, an American citizen, purchased the weapon found in his possession. They also cited the weapon’s illegal modification as a significant aggravating factor, while his legal team pushed back against claims that the artist was involved in any organized criminal activity.
Court documents also alleged that Squash entered the U.S. illegally.
His legal troubles in the U.S. mirror previous scrutiny he faced in Jamaica. In 2018, Squash was detained during a State of Emergency (SOE) sweep in St. James, launched in response to escalating crime in the parish. He spent five months in custody without charge before being released in January 2019—just one day before the SOE expired.
He left Jamaica to perform in the United States for the first time in September 2019.
In a 2022 interview, Squash opened up about the pressures that drove him away from the island, citing “corruption” within his circle and discomfort with “the system.”
“Mi cyah tek the hold down in Jamaica and corruption in my little circle, Jamaica small bad enuh, the world big and Jamaica have too much corruption in one little environment and mi cyah deal wid it,” he explained.
Despite the gritty persona reflected in his street anthems like Big Breeze, Know Bout That , and Rate Who Rate You, Squash insisted he is misunderstood. “You see me now, me is not a violent man, people out there might see 6ixx boss and have me as violent, but I am a jovial person, me loving and kind, fun, mi like happiness, me nuh like sadness,” he said at the time.
The artist, who boasts over 260,000 followers on Spotify and has released projects such as F.A.M.E (Faith Always Move Everything) and Hate Being Famous.