Bill Belichick’s offseason has taken a litigious turn after a considerable lull. Instead of playbook details, the legendary coach is dealing with a six-figure premises liability lawsuit. The filing alleges that hazardous working conditions at his Nantucket property led to severe injuries.

As per the Nantucket Current, a local painter filed a lawsuit against Forty Five Fair Street LLC, managed by Bill 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. Real estate records show Belichick uses the LLC to manage his private assets. Because he is listed as the primary manager of the company, Jackson’s legal team is holding him personally liable for the site’s daily safety standards.

“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 receiving initial workers’ compensation, Jackson retained his right to pursue third-party negligence. He argues that the LLC is directly responsible for the unsafe environment that caused the fall, leaving him with mounting out-of-pocket expenses. 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 probably 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 at 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. On the coaching side of things, Belichick isn’t getting a break there either, as a Gamecocks alum has shown some dissent toward the legendary coach.

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.”

For now, Bill Belichick has not publicly commented on the lawsuit. But with nearly #300,000 on the line and a negligence case officially filed in court, the matter is unlikely to go away quietly. It’s a headache the veteran coach could have done without, especially with a new season at UNC around the corner.