Dancehall entertainer Squash is scheduled to be released from federal prison in the United States in January 2027, according to records from the Federal Bureau of Prisons.
The St. James–born artist, whose real name is Andrae Maurice Whittaker, is currently housed at the Federal Detention Center (FDC) in Miami and is listed for release on January 25, 2027. The date represents roughly 80 per cent of his full sentence, a standard threshold for inmates convicted in federal court who qualify for release based on good behaviour.
Whittaker was sentenced on Monday, November 24, to two years and three months in federal prison after pleading guilty to possession of a firearm while living in the United States illegally. The case stemmed from his arrest during a traffic stop in Miami in early 2025, when law enforcement recovered a firearm from the vehicle in which he was traveling. Authorities said the weapon had been modified with a switch, commonly referred to in Jamaica as a “chip glock.”
Following his arrest, Whittaker was transferred to U.S. Immigration and Customs Enforcement (ICE) custody and later entered a plea agreement admitting to the firearm offence as an undocumented immigrant.
U.S. prosecutors had then alleged during court proceedings that Squash was the head of a “transnational criminal organization,” claiming he entered the United States illegally in January 2021 after fleeing Jamaica amid a deadly gang feud. His legal team has consistently rejected allegations made by federal authorities that he is the leader of an organised criminal gang.
Court documents also stated that he had previously been detained by ICE and released on bond after marrying an American citizen, who authorities allege purchased one of the firearms linked to the case.
Squash, a native of Salt Spring in Montego Bay, initially pleaded not guilty to charges including illegal possession of a modified weapon and carrying a concealed firearm without a permit, before later changing his plea. The sentencing brought months of legal proceedings to an end.
Upon completion of his sentence, he is expected to face further immigration action. Whittaker remains housed at FDC Miami, an administrative-security federal detention facility located in downtown Miami, until his scheduled release in 2027.
