Incarcerated dancehall artiste Squash has received another reduction in his U.S. prison sentence, bringing his projected release date forward to November 26, 2026.
The latest adjustment means the entertainer, whose real name is Andrae Maurice Whittaker, has had 60 days shaved off his sentence since the beginning of the year, putting him on track to spend less than a year behind bars.
Squash was sentenced in November 2025 to 27 months’ imprisonment after pleading guilty to being an alien in possession of a firearm.
The conviction stemmed from a February 2025 traffic stop in Miami, Florida, during which law enforcement officers recovered two firearms from a vehicle linked to the entertainer.
According to court documents, both weapons were legally owned by Squash’s wife. However, prosecutors argued that Squash was unlawfully present in the United States after re-entering the country following his deportation to Jamaica in 2019, making his possession of the firearms a federal offence.
He subsequently entered a guilty plea.
During his incarceration, Squash filed a lawsuit against the U.S. Bureau of Prisons, alleging that he had been improperly denied access to sentence-reduction programmes that could have shortened his prison term. He later voluntarily withdrew the lawsuit, prompting the court to dismiss the matter.
Despite abandoning the legal challenge, Squash has continued to benefit from sentence reductions, with his projected release date now advanced by a total of two months.
His legal issues, however, are far from over.
Upon completing his prison sentence, the deejay is expected to remain in federal custody because he is subject to an immigration detainer that has been in place since his arrest in February 2025.
As part of his plea agreement, Squash acknowledged that his conviction could carry immigration consequences, including deportation. Any decision regarding his removal from the United States will ultimately be made by an immigration judge during separate removal proceedings.
This is not the first time the entertainer has encountered immigration authorities.
In 2024, Squash was detained by U.S. Immigration and Customs Enforcement (ICE) after another traffic stop during which firearms were recovered. Although he was never criminally charged in that incident, he remained in immigration custody before later securing his release after marrying while detained.
With his prison release now just months away, attention is expected to shift from the federal correctional system to the U.S. immigration courts, where the next chapter of the dancehall star’s legal battle will be decided.
