Jamaican dancehall artiste Squash, whose real name is Andrae Maurice Whittaker, is facing serious legal trouble in the United States, where federal authorities reportedly identify him as the leader of a transnational criminal organization.
The 32-year-old entertainer faces two counts, along with forfeiture allegations, stemming from his February 24 arrest during a traffic stop in Miami, where law enforcement reportedly discovered a modified Glock pistol in the glove compartment of the vehicle he was traveling in. He has pleaded not guilty to charges of illegal possession of a modified firearm and carrying a concealed weapon without a permit.
The case took a sharp turn in May, when federal prosecutors reportedly sealed a criminal complaint against him. By May 27, after his legal team filed over two dozen motions, a trial date was set—prompting federal officials to step in, asserting their intent to take over the case.
Federal authorities claim Squash is a known figure to law enforcement and accuse him of leading the G-City Gang, which they say has been involved in violent criminal activity that originated in St. James, Jamaica, and later extended to Florida.
Court filings indicate Squash first entered the U.S. legally in May 2019 but later re-entered illegally in January 2021, allegedly crossing the border without inspection. In 2023, he reportedly had his first documented encounter with law enforcement in the U.S. during a traffic stop involving officials from the Broward Sheriff’s Office.
An informant is said to have told authorities that Squash fled Jamaica to escape a deadly gang feud and entered the U.S. unlawfully. Immigration authorities later detained him, but he was released on bond after marrying an American citizen while in custody.
Notably, the same woman is said to have purchased one of the weapons linked to Squash in his current charges.
Federal investigators believe they have probable cause to charge Squash with being an illegal alien in possession of a firearm and unlawful possession of a machine gun. If convicted, he faces up to 10 years in prison per charge, with the potential for a mandatory 15-year minimum if prior convictions are found. Deportation is also a likely consequence.
Squash remains in federal custody at the Miami Detention Center, with trial set to begin on September 2 in the Southern District of Florida. He has until August 26 to accept a plea deal and avoid trial.
