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Bill Belichick (Associated Press)

Krause: The Hoodie is a jet-setter. Wise?

Steve Krause

August 27, 2025 by Steve Krause

As Cracker Barrel found out this week, rebranding can be risky business. Either you knock it out of the park or you fumble on the goal line.

We already know about Cracker Barrel. Pick six.

Closer to home and on an entirely different subject, Bill Belichick has been navigating the shark-infested waters of personal rebranding, hasn’t he?

The old curmudgeon who wouldn’t tell you if you were on fire – and would growl at you like a lion if he were to lower himself to talk to little old you – now wants to shed his skin and join the world of college sports, where spin and positive publicity rule.

All I can say is “good luck.”

This all started when the old sourpuss and his longtime squeeze, Linda Holliday, who is only 10 years younger than the 73-year-old Belichick, split.

Not that I’m any expert on relationships, but that seemed odd. They seemed like a Travis-Tay Tay special.

What came next was more odd, though. Now, the man whose face looks like it’s going to crack if he breaks into a smile, is squiring 24-year-old Jordon Hudson around.

Do that math . . .

How ridiculous is this? She filed a trademark application for the term “gold digger.”

Along similar outrageous lines, the guy who once rode with me to the top floor of the Patriots’ media complex (eight floors for those interested) without acknowledging me once, wants to start a media venture called “Belecast.”

Bill the media mogul.

After a while of suffering through Belichick’s one-word answers during postgame news conferences, I deduced that no one can be this much of a jerk without really working at it. So he must be working to perfect his brand as the perfectly-formed backside of a horse.

But God love Jordon. She’s brought him out of his shell and put him into more ridiculous situations. His new brand must be “Bon Vivant Bill.”

How else do you explain this transformation? Hobnobbing with the Mannings on Monday Night Football? Appearing on weekly telecasts with the painful-looking smile plastered onto his face?

And to think. He’s going to be coaching college kids? With the firm hands and guidance they need in this world? That’s going to go over big, I assure you.

To add to all this, Hulu is going to feature the North Carolina Tar Heels, which the university sees as a great way for it to rise to the upper echelons of college football. Sure it will. But how long do you think it will take for some wiseguy (or woman) to try to get away with a veiled insult at the expense of “Young Hoodie Hudson?”

The best example of “Bon Vivant Bill,” though, is the news that he’s selling his Nantucket cottage for a cool $4 million. This really caught my eye because I used to go to a cottage on Emerald Avenue in Hampton Beach every summer. Our family, which consisted of seven aunts and uncles and 28 cousins, each took a week.

The cottage was as big, maybe, as one room in the Hoodie manse in Nantucket, and it is pretty much what I think of when I hear the word “cottage.” By the time it was razed, a decade ago, it was listing further sideways than the Leaning Tower of Pisa.

But $4 million? In our case, maybe $4 would be too much.

Whoever bought our little cottage put up what I call “The Emerald Palace” in its place, and can I just say it looks ridiculously out of place with the seasonals that dot the neighborhood?

Selling his Nantucket cottage for $4 million is Belichick’s right. What he does with his real estate is his business. But this transition to a “Bon Vivant Bill,” showing up here and there with “Young Hoodie Hudson,” managing million-dollar transactions on Nantucket, and other uncharacteristic activities, seems a bit much, if you ask me.

  • Steve Krause
    Steve Krause

    Steve Krause is the Item’s writer-at-large. He joined paper in 1979 as a copy editor and later created a music column, called Midnight Ramblings, which ran through 1985. After leaving the paper for a year, he returned in 1988 as a reporter and editor in sports. He became sports editor in 1998; and was named writer-at-large in 2018. Krause won awards for writing in 1985 from United Press International; in 2001 from the Associated Press; and again in 2020 from the New England Newspaper & Press Association. He is a member of the Harry Agganis Foundation Hall of Fame, a past winner of the Moynihan Lumber Scholar-Athlete Community Service Award, and was the 2012 recipient of the Jack Grinold Media Award for MasterSports, an organization that conducts high school and college coaches’ clinics. He lives in Lynn, is active on Facebook, and can be found on Twitter @itemkrause.

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