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Reading: Fresh Legal Battle Looms for Squash: Florida Woman Files Lawsuit for US$30,000 Just Months Before His Release From Prison
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Home » Fresh Legal Battle Looms for Squash: Florida Woman Files Lawsuit for US$30,000 Just Months Before His Release From Prison
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Fresh Legal Battle Looms for Squash: Florida Woman Files Lawsuit for US$30,000 Just Months Before His Release From Prison

Shadow
Shadow August 5, 2026
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Fresh Legal Battle Looms for Squash: Florida Woman Files Lawsuit for US,000 Just Months Before His Release From Prison
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Dancehall artiste Squash is facing fresh legal trouble just months before his projected release from a U.S. federal prison. A Florida woman has filed a civil lawsuit accusing the entertainer of fraud and civil theft, alleging she paid him US$10,000 for a music collaboration that was never completed and is now seeking US$30,000 in damages. Squash has denied the allegations, arguing there was no written contract and asking the court to dismiss the case.

According to court filings, the woman, identified as Danaisia Alston, alleges she entered into a verbal agreement with Squash, whose given name is Andrae Maurice Whittaker, after meeting him around June 1, 2022 while he was filming the music video for Don Dada. Alston claims the collaboration was intended to promote her independent label, JG Recordz, and that she paid a total of US$10,000 in two instalments of US$5,000 each. She alleges the first payment was made to one of Squash’s associates on June 3, 2022, while the second was paid directly to the entertainer on July 9, 2022. According to her claim, the song was never delivered despite repeated assurances. She further alleges Squash delayed the project with various excuses, including claiming he was too intoxicated to record, before eventually changing his telephone number and ceasing communication through Instagram.

Alston is seeking US$30,000 in damages, which she says reflects the treble damages permitted under Florida law for civil theft claims. She is also asking the court to award court costs and any additional consequential damages allowed by law. In an affidavit filed on July 27, she submitted alleged WhatsApp conversations and Instagram direct messages that she says support her version of events. She also claims the alleged loss left her in severe financial difficulty, forcing her into debt after pawning a valuable personal item to raise the funds. According to the filing, the financial strain ultimately contributed to the loss of her apartment and vehicle, while also affecting her mental health and ability to operate her business. Alston further stated that she delayed filing the lawsuit for four years because she could not afford legal representation and was unaware she could bring the claim herself. Court records indicate she later obtained indigent status, allowing her to proceed without paying filing costs.

In response, attorney James Stark, representing Squash, denied the allegations in a filing submitted on July 16. The defence argues that Alston failed to produce a written contract supporting her claim and also criticised her original handwritten complaint as being largely illegible. Squash has asked the court to dismiss the lawsuit with prejudice. As of August 4, he had not filed a response to Alston’s subsequent affidavit.

The civil dispute comes as Squash continues to await his release from the Federal Correctional Institution in Oakdale, Louisiana. The entertainer’s projected release date was recently moved forward to November 26, 2026 following a third sentence reduction this year. However, his legal challenges are far from over. While the civil lawsuit remains in its early stages and no hearing date has been scheduled, the outcome could add another chapter to the dancehall star’s ongoing legal battles as he prepares to leave federal custody. The allegations in the lawsuit have not been proven in court, and the matter remains before the court for determination.

 

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TAGGED: alkaline, Andrae Maurice Whittaker, Caribbean News, celebrity lawsuit, chronic law, civil theft, Danaisia Alston, dancehall music, Dancehall News, Don Dada, entertainment, entertainment news, FCI Oakdale, First Step Act, Florida lawsuit, fraud lawsuit, Instagram DMs, jamaica, Jamaican artiste, James Stark, JG Recordz, legal battle, Let's Be Honest, music collaboration, music industry, prism marketing consultants, Prison Release, raymond Small, shadow, squash, the fix, U.S. federal prison, vybz kartel, Wearedancehall, WhatsApp messages
Shadow August 5, 2026
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