Remember when Jason Whitlock threw down some serious shade about Bill Belichick and Jordon Hudson’s relationship? He went on his “Fearless” podcast and didn’t mince words, saying, “This is a mistake. I keep going back over and over and over again. This isn’t going to work. This is going to be a massive flop. This guy, he’s lost his mind.” And that was after labeling the UNC coach a “clown,” putting him in the same boat as Kanye West and Hunter Biden. Looks like Whitlock is not about to bury the hatchet anytime soon. As he keeps highlighting the 49-year age gap, you’ve got to wonder if Whitlock should tread a little more carefully, especially since Hudson seems ready to fiercely defend her man’s reputation.

Belichick and Hudson’s story reportedly started like something out of a movie—a chance meeting on a flight from Boston to Florida in February 2021. Apparently, it was pretty much love at first sight. Ever since then, they’ve been inseparable. It’s gotten to the point where Hudson is deeply involved in pretty much everything Belichick does. She even signs emails as the ‘chief operating officer of Belichick Productions.’ And Belichick, the GOAT with eight Super Bowl rings, whose UNC emails are public record, has asked for Hudson to be copied on all his emails. All this public display of affection hasn’t gone unnoticed, drawing some serious side-eyes from fans and well-known figures alike.

Fresh off a spring break trip that included a museum date and a beach yoga pose that went viral for all the wrong reasons, Belichick’s girlfriend celebrated her birthday. But another controversy was brewing, this time over her outfit choice for UNC’s “Practice Like a Pro” spring football event. Of course, this didn’t escape Whitlock’s attention.

On his April 15th podcast, Jason Whitlock didn’t hold back: “Put the picture of the woman in the boots and all this look, none of this makes sense in terms of 73 and 24. This is how she’s dressed, helping Bill Belichick at their spring game or some practice or whatever. It doesn’t make sense.” So, what’s the big deal?

Lately, Jordon has been seen sporting a lot of UNC jerseys and gear. However, for the spring practice, she opted for a look that was far from school spirit—a long coat, a skirt, and white boots, looking more runway-ready than football-field appropriate. “Bill Belichick was the guy that hated distractions. You telling me this isn’t a distraction?”

Whitlock put more of the blame on Belichick, arguing that someone with his long history and established reputation in the game should know and act better. As he pointed out, “The female trainers that taped your ankles and brought you ice and cold water to drink they were always a target among the football team and players, and they weren’t dressed like this…Bill is putting a target on this girl’s back.” Turns out that Hudson is now more bothered about her new role.

Bill Belichick’s CEO girlfriend takes charge

Maybe the criticism has gone too far because it looks like Belichick’s girlfriend is now taking matters into her own hands. Having been by his side on red carpets, in a Dunkin’ commercial, and even included in all his work emails, Jordon Hudson has now launched a new project of her own. On April 15th, the former cheerleader teased her new venture on Instagram, saying, “For those who don’t know me…” before revealing, “👋🏼Hi, my name is Jordon Hudson. I’m the Founder and CEO of Trouble Cub Enterprises.🐻🧡” So, what exactly is this “Trouble Cub Enterprise”?

Hudson’s LinkedIn profile also lists her as the CEO and founder of the company. Her mission? To reclaim the trademarks of various phrases Belichick coined, which are currently owned by Robert Kraft and the New England Patriots. She wants Trouble Cub Enterprise to own phrases like “Do Your Job” and “Ignore the Noise.” This move has raised eyebrows, drawing comparisons to Taylor Swift’s battle with Scooter Braun over the rights to her early music.

Adding another layer, Jordon Hudson has been seen sporting looks reminiscent of Swift. In an April 13th post, she wore a snakeskin outfit while Swift’s “Vigilante S–t,” a song believed to be about her feud with Braun, played in the background. Perhaps feeling the intensity of the scrutiny, Hudson’s new venture suggests a move to shape her own narrative.