A routine paint job at a historic Nantucket address has turned into a six-figure court fight tied to one of football's most famous coaches. Local painter Andrew Jackson has filed a negligence lawsuit over a fall he says left him with a serious ankle injury while working at 45 Fair Street, a property owned through a company managed by Bill Belichick. Jackson says he slipped on June 21, 2024, later needing surgery for what the complaint calls a "severe right ankle injury." The suit, filed this week in Nantucket Superior Court, names Forty Five Fair Street LLC as the defendant and asks for roughly $300,000 in damages to be determined at trial.
What the Complaint Alleges
According to Nantucket Current, Jackson claims he fell after stepping on plastic sheeting and other coverings that he says turned the work site into a hazard. The complaint argues that the way those materials were placed, used, and maintained directly led to his fall. Jackson says he has endured pain, disability, and mounting medical expenses, and is now seeking payment for lost wages and diminished earning capacity. His attorney, Isabela Orlacchio‑Garcia, notes that while Jackson has received workers' compensation benefits, he is pressing a separate third‑party negligence claim against the property owner.
Filing and Damages Sought
The complaint landed in Nantucket Superior Court on Thursday, according to Daily Voice. Local coverage has tallied the claimed losses: hospital and therapy bills of about $67,000, documented lost wages nearing $168,000, and another $50,000 in anticipated future earnings. Together, those figures approach $285,000, per ACK. On top of that, the suit asks for pre‑ and post‑judgment interest, court costs, and "any other relief" a judge might think is appropriate.
Owner and Property Background
Belichick picked up the downtown Fair Street house last spring for about $4.8 million through a limited liability company, according to Boston.com. The complaint identifies Forty Five Fair Street LLC as the property's owner and lists Belichick as the LLC's manager, per local reporting. The former Patriots coach is also reported to own other Nantucket real estate, and island property watchers have tracked several of his purchases over the years.
Legal Context and Next Steps
Jackson's lawyer has told reporters that he received workers' compensation but is still pursuing a third‑party negligence claim against the property owner, a setup described in coverage by Nantucket Current. Under Massachusetts law, injured workers can bring third‑party suits even after collecting benefits, although insurers may try to recoup some of what they paid through subrogation rights under the workers' compensation statute. Courts have wrestled with that balance in cases such as DiCarlo v. Suffolk Construction. How any eventual recovery in Jackson's case might be divided between him and any insurer or subrogee would likely be sorted out in court filings or settlement negotiations as the case moves along.
What's Next
The lawsuit now joins the regular civil docket in Nantucket Superior Court, where pretrial schedules and hearings will be set in the coming months. As the case proceeds, filings - including the complaint and any motions that follow - are expected to be available to the public through the court.
