September 2023: People reports that Belichick and entrepreneur Linda Holliday have ended their 16-year relationship. Per People ’s source, the couple had been “pretty separate for a while.” As for the cause of the breakup, the insider said that the relationship had simply “run its course.”

Bill Belichick and Jordon Hudson, who have a nearly 50-year age gap, began dating years after their first meeting in 2021.

UNC head coach Bill Belichick renamed his boat with a cryptic message amid rumors that he and his girlfriend, Jordon Hudson, are engaged