The Bill Belichick and Jordon Hudson saga has become the talk of the football world. Sports media personalities and pundits alike have weighed in, debating whether it’s appropriate for a 24-year-old woman to date a 73-year-old man. Most recently, Colin Cowherd added his voice to the conversation, and surprisingly, he pushed back against the prevailing criticism.
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At first glance, the concern about Belichick being with Hudson pertained to his legacy and how others viewed him. Some believe his legacy is practically tarnished, and the conversation has shifted to what Hudson wants out of the relationship. Recently, the Belichicks voiced their concerns, saying they’re “extremely concerned” over the blossoming relationship.
So, the argument simply is that Belichick could be being taken advantage of. But Cowherd believes it’s not like we haven’t seen this type of relationship with a huge age gap before.
Cowherd unpacked their relationship and their current family financial standing, drawing the conclusion that the two are simply helping each other out. Which made sense the way Cowherd put it.
“Stop me if you’ve heard this before: a wealthy old man starts dating a young, ambitious woman, and suddenly the family is concerned,” Cowherd pointed out (via The Herd).
“Look, I don’t buy into this idea that Bill is some old, feeble man who doesn’t know what he’s doing. We’ve literally got Ring video proving Bill knows exactly what he’s doing. Put your shirt on, Bill.”
Cowherd was referencing a Ring video that went viral in November of 2023. Belichick was captured, shirtless, sneaking out of his girlfriend’s home. The video went viral more out of hilarity than anything else, but the Belichicks have also stated they “worry” about potential blackmail related to the footage, which might have contributed to the Bill-Jordon situation.
Yet, it’s no surprise that the Belichick family has expressed so much recent concern over Bill and his antics. After all, he’s the one with all the money, and surely the family wants to protect that. Cowherd can see this from a mile away.
“Let’s be honest, families aren’t worried about Bill; they’re worried about the will. When dad’s worth over $100 million, suddenly everyone’s got questions, like, ‘Who’s getting cut out?’ You really think Belichick, architect of the greatest dynasty in NFL history, lost his playbook in the last 8 months? C’mon,” Cowherd argued.
It’s almost like the movie Knives Out playing out in real life. Bill is worth all the money, and the family wants to know if that money is going to be given to anyone outside of it. They might feel like they have a right to know, but the truth is, it’s all up to Bill.
Sunday thoughts on Bill Belichick & Jordon Hudson pic.twitter.com/Pe8BDdBk6s
— Colin Cowherd (@colincowherd) May 18, 2025
At the end of the day, though, Cowherd says he sees nothing wrong with this “strategic partnership” that Bill has concocted. He was essentially ignored and pushed out of the NFL, and now he needs to rebrand in college during the latter stages of his life. Hudson has made him seem more hip and cool, keeping him relevant through her knowledge of social media. What’s wrong with that?
Both Belichick and Hudson get something out of the relationship. Furthermore, Cowherd thinks that the two do genuinely enjoy each other’s company.
“Don’t pretend this is brand new behavior. DiCaprio has made a career out of it… If Bill was 93 and found barefoot, walking through a truck stop, yeah, we could all worry. But he’s not being held in a basement. She’s not spoon-feeding him oatmeal. They’re busy building their own brand in Chapel Hill, no less.”
Leonardo DiCaprio has indeed become popular over the years for dating women he’s over twice their age. So, why does everyone have so many concerns about Belichick? It’s not like he’s completely decrepit, like Howard Marshall was when he married Anna Nicole Smith at 89. That would make it far more controversial.
It may be unfortunate to admit, given how taboo the relationship looks, but Belichick has played a smart hand since officially announcing he’s with Hudson. His media stock has risen exponentially, and he went from being a boring old football coach to a cool guy overnight. And did anyone know that Hudson’s family business just went under? So, she played her cards right as well.
It’s time for us to throw in the towel and let this relationship be. We’ve beaten it to death at this point, trying to highlight potential controversies. Maybe more will be revealed in time. But for now, Belichick seems happy to be with Hudson, just like Cowherd points out.
