Bill Belichick is pushing for a jury trial in a legal dispute with a Nantucket painter who is suing him for $300,000, alleging injury due to unsafe conditions on the former NFL coach's property.

Andrew Jackson, a painter, filed a lawsuit in April claiming he sustained a severe ankle injury in June 2024 after falling on Belichick's Fair Street home due to what he described as "dangerous and unsafe" working conditions. Jackson is seeking nearly $300,000 for medical expenses, lost wages, and other damages. According to court documents, Jackson incurred approximately $61,000 in hospital bills, $4,600 for doctor's visits, and $2,000 for physical therapy. He also claimed to have lost $167,828.25 in wages and anticipates future losses of $50,000.

In response, Belichick has filed a complaint against Levesque Builders Inc., the construction firm that managed the painting work. Belichick's legal team contends that Levesque Builders Inc. was solely responsible for the direction, control, management, and supervision of Jackson's work. Belichick's complaint states that "If Mr. Jackson was injured while performing painting work at the Property – which 45 LLC denies – his injuries were sustained as a result either of his own negligence or fault in performing the work, or Levesque’s negligence or fault in failing to direct, control, manage and/or supervise the work."

Jackson's lawsuit alleges that the home's improperly maintained plastic sheeting or coverings created a hazardous environment. He claims Belichick owed a duty to maintain the premises safely, inspect for hazards, warn of dangers, and coordinate the site appropriately for workers.

Belichick, 74, owns the Nantucket property with his girlfriend, Jordon Hudson, 25. This legal battle comes as Belichick prepares for his second season as head coach of the UNC Tar Heels, whose season opener is scheduled for August 29 against TCU. The team's preparations have also been impacted by a university investigation into GM Michael Lombardi following a complaint from a former staffer.