Bill Belichick’s offseason has taken a litigious turn after a considerable lull. The legendary coach, obsessed with controlling every detail on the field, is now facing a multi-million-dollar lawsuit alleging a chaotic, dangerous environment at his Nantucket estate.

As per the Nantucket Current, a local painter filed a lawsuit against Forty Five Fair Street LLC, managed by Belichick, alleging that he fell during the painting job due to “unsafe” conditions and broke his ankle in July 2024. The painter is seeking around $300,000 in damages.

“As a direct and proximate result of defendant’s negligence,” the lawsuit stated. “Plaintiff has suffered and continues to suffer bodily injury, physical pain and suffering, mental anguish and emotional distress, medical expenses, lost wages and impairment of earning capacity, loss of function and enjoyment of life, and such other damages as may be proven at trial.”

Despite Jackson receiving workers’ compensation from his employer before filing the suit, Jackson’s lawyer, Isabela Orlacchio Garcia, alleges it wasn’t sufficient to cover his damages. According to the lawsuit, Jackson incurred $61,000 in hospital expenses, $4,600 in doctor visits, and $2,000 in physical therapy bills. Additionally, Jackson alleges that he lost $167,828 in wages and will likely lose another $50,000.

“Defendant owed Plaintiff a duty to use reasonable care to maintain the premises in a reasonably safe condition,” the lawsuit reads. “To inspect for hazards, to warn of dangers of which it knew or should have known, and to coordinate the site in a reasonably safe manner for lawful workers present there.”

The 73-year-old UNC head coach bought the property on 45 Fair Street through an LLC for around $5 million two years ago. According to the documents, Belichick owns the 2,854-square-foot property with his girlfriend, Jordon Hudson.

A former UNC player throws Bill Belichick under the bus

After a disappointing 4-win season in 2025, the pressure is on for a significant turnaround. To that end, Belichick has aggressively reshaped the team by landing 41 commits and 20 transfers, but this flurry of activity has not convinced everyone that the program can achieve its target of 8 or 9 wins.

“I will not be attending any UNC football games this year! The things I’m hearing, man, I would have never thought 💔,” former UNC player Marquise Williams wrote on X in March.

Williams is a two-time all-ACC QB for the program, and Tar Heel fandom runs thick in his blood. However, his doubts about Bill Belichick’s 2026 season hopes might just signal trouble brewing in the background. The former QB didn’t explain his reason for his X post. But when a fan pressed to explain it, he simply replied, “Shut up.”