What Happened Between Bill Belichick & His Ex Linda Holliday?

Bill Belichick may be known for his relationship with Tom Brady, but he had a romantic relationship that lasted nearly as long. The NFL coach dated Linda Holliday from 2007 until September 2023. When their split was reported by Page Six, a source told the outlet that the former couple had a protracted breakup that lasted over a year. Reportedly, Holliday was still staying at Belichick's home in Nantucket post-breakup because she was in no hurry to leave the community where she had a large group of friends. The publication also reported that there was worry among New England Patriots executives that the shady side of Bill Belichick would be exposed by Holliday after the pair split.

There were other issues for Belichick and his ex-girlfriend to resolve such as what to do with their home in Jupiter, Florida. "Bill bought a house in Jupiter for himself and Linda, but now she will get the house," a source told People at the time of the couple's breakup. "He doesn't want a lot of public attention on this," the insider said of the notoriously private football coach.

Besides working out their living situation, the former couple needed to address Holliday's standing with The Bill Belichick Foundation, the charitable organization she was a major part of during their relationship. The pair appeared to stay on good terms, as Holliday remained listed as the president of the foundation.

Why Bill Belichick and Linda Holliday continued working together

Linda Holliday stayed on as the president of Bill Belichick's charity after their breakup, as evidenced by the foundation's website, and Holliday's Instagram bio. Maintaining her position as president of the organization was not the only indicator that Holliday and the former New England Patriots coach were on good terms. Unlike most breakups, Holliday kept all the photos of her ex-boyfriend on her Instagram page, including a post from February 2017 where she called Belichick "my hero" after the Patriots won the Super Bowl.

Seeing the former couple continue their charitable work together was not altogether surprising as they were a great off-the-field team. The Bill Belichick Foundation (BBF), which gives scholarships to young athletes and donates to football and lacrosse teams in need of financial aid, expanded the scope of their mission thanks to Holliday. "For years, Bill had been donating a scholarship to one student athlete in memory of his father. But we wanted to take this a lot further," she told Boston.com in November 2017. Holliday and Belichick's charitable work was recognized in April 2019 when they were awarded the Carolyn Lynch Humanitarian Award for raising money for breast cancer research through the BBF. "Linda, thank you for broadening my vision, brightening our world and reaching our journey," Belichick said during the ceremony, per CBS News.

The duo were a great fit running a charity together, but Holliday's ostentatious personality was a stark contrast to the stoic Belichick.

Linda Holliday's uncomfortable online posts

In January 2021, Linda Holliday put the spotlight on the infamous fallout between Bill Belichick and Tom Brady. While Brady's new team, the Tampa Bay Buccaneers, was in the middle of a playoff game against the New Orleans Saints, Holliday got into an online spat with cantankerous fans on Instagram. "And you have all the answers evidently?" Holliday replied to a commenter who bemoaned that Belichick let Brady leave the Patriots (via CBS News). "Tom didn't score [Sunday] night ... not once! Defense won that game. Were you even watching," she added. The altercation reportedly brought unwanted attention to Belichick after going viral. "So, he's feeling it, because you know he's in front of the TV when Linda's next to him. You know they're feeling it," sports analyst Michael Felger pointed out on 98.5 The Sports Hub (via CBS News). After being bombarded by trolls, Holliday temporarily set her Instagram to private.

Holliday had never been shy about sharing her thoughts on Instagram, even when they involved Belichick. The couple attended the White House Correspondents' Dinner in April 2015, and Holliday reshared a snap of Bill Belichick seemingly taking a gander at Chrissy Teigen's backside. "I mean, honestly, who didn't check her out in this photo?!? I think I even looked!" Holliday wrote in the caption.

A couple years later, a June 2017 photoshoot of Holliday and Belichick for Nantucket Magazine became the subject of ridicule. Holliday posed with a sweet smile while Belichick looked deathly serious. "Love, exciting and new," one X, formerly Twitter, user wrote in jest while retweeting the snaps. In retrospect, Belichick's grim demeanor may have been a sign of trouble in paradise.