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By Conor Ryan
Bill Belichick and his girlfriend, Jordon Hudson, have found themselves in the headlines for all of the wrong reasons following an awkward interview on CBS Sunday Morning last month.
Most of the discourse surrounding the couple has revolved around their relationship and Hudson’s potential influence over the legendary head coach.
But longtime Boston sports scribe Bill Simmons believes that some of this drama also sheds light on the machinations that ended the Patriots’ two-decade dynasty.
In particular, Simmons believes that an email penned by Belichick that Hudson shared on Instagram offered insight into just how the relationship between Belichick and Tom Brady eroded over their final years together in New England.
Days after that CBS interview, Hudson posted a screenshot of an email from Belichick that both bemoaned the media scrutiny regarding his new book, “The Art of Winning: Lessons from My Life in Football” and presented the strategy for how to best market the tome.
“I will say again, that I want this book to be presented as a look at my professional life and how I did my job on the way up to, and as the leader of an organization that grew from a $500 [million] franchise to an $8 [billion] organization that played in 10 and won 6 Super Bowls over 25 years,” Belichick noted in the email.
For Simmons, Belichick’s emphasis on his own achievements in building up New England’s success (and value) seemingly explained “a lot about what happened” between Brady and his former head coach.
“Everyone was like, ‘Patriot Way, Patriot Way, we’re just about Super Bowls,'” Simmons said on “The Bill Simmons Podcast” this week. “But there was clearly some sort of ego thing and it’s two guys that really understood their place in history in a whole bunch of different ways, right?
“It was always like, ‘We’re in this together. There’s no credit.’ But the credit thing was a big part of it and [Jimmy] Garoppolo is in there and [Brady’s] really thinking about — I never wanted to believe it.
“I never, when [ESPN’ Seth] Wickersham and people like that were reporting about it, and I was like, [expletive] that. I don’t wanna hear this. Stop trying to cause trouble.’ But there clearly was a ton of trouble.
Even though both Brady and Belichick played critical roles in establishing New England as an NFL juggernaut, the debate over which one held greater sway over the Patriots’ fortunes eventually led to resentment, in the eyes of Simmons.
“I think that really explained to me why Brady didn’t end up [re-signing] with the Patriots because what everybody was writing about and doing the sports radio topic of ‘who’s more responsible for all the Super Bowls: Belichick or Brady?’ And the right answer was always both,” Simmons said. “They needed each other and that’s the answer.
“But clearly, they both kind of thought each of them was more responsible than the other. So when I read that paragraph [in Belichick’s email], I thought, ‘Man, Belichick must have been so pissed when Brady had that Tampa season where he won the title. Because clearly he does give a [expletive] about all this stuff.”
While that icy sentiment between Brady and Belichick eventually led to the former leaving for Tampa Bay in March 2020, Brady seems to have mended fences with his longtime coach now that both are no longer in Foxborough.
“To Coach Belichick, thank you for your tireless commitment to develop and push me to be my very best. It wasn’t me, it wasn’t you, it was us,” Brady said at his Patriots Hall of Fame induction ceremony in June 2024. “Our hard work, our love of the game, and the way we worked for one another, that’s what it was all about.
“Let me make this crystal clear: There is no coach in the world I would rather play for than Bill Belichick.”
Conor Ryan is a staff writer covering the Bruins, Celtics, Patriots, and Red Sox for Boston.com, a role he has held since 2023.
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