Bill Belichick’s Girlfriend Says 2026 Kentucky Derby Isn’t 1st Time They’ve ‘Trudged Through’ Mud

Bill Belichick and his girlfriend, Jordan Hudson, expertly matched at the 2026 Kentucky Derby — and used their attendance at the iconic event to seemingly shade their haters.

Belichick, 74, sported a pastel blue suit with a pale pink shirt and tie to Churchill Downs on Saturday, May 2. His outfit coordinated with the colors of Hudson’s strapless gown. Hudson, 25, opted for a gown with a blue bodice and pink floral appliqués dotting the skirt.

True to classic Derby style, Hudson topped off her look with a hot pink fascinator.

“Not the first time we’ve trudged through the mud together. 🤝🏻🐎,” Hudson captioned Instagram photos of the couples race-day ensembles, seemingly referring to the hate they’ve received for their age-gap romance.

Hudson and Belichick have been together since 2021, during which they’ve raised eyebrows for their 49-year age difference. Despite the critics, Hudson and the former NFL coach have fiercely defended their relationship.

“I stay focused on football and, some of the other opportunities that come along, Jordon looks at those and can dig into them a little bit deeper,” Belichick said on “The Pivot” podcast in May 2025, denying Hudson’s involvement in his profession. “But really, what she does is help me spend my time on football, and that’s what’s important to me.”

Belichick further stressed that Hudson has “nothing” to do with his coaching position. (He is currently the head coach for the University of North Carolina Tar Heel’s football team.)

“It would be personal opportunities, [like] a speaking thing, appearance on this or talk about this or somebody happens to want an autograph, that type of thing,” he explained at the time. “She kind of [helps] organize that for me. … Jordon has her own businesses and she’s savvy in those. I’m football and I let her help me with business.”

Hudson’s help also extended to the creation of Belichick’s memoir, The Art of Winning: Lessons from My Life in Football.

“There were certain things in the book, as I was writing it, that she looked at from a business perspective,” Belichick added on the podcast. “It didn’t really fit the business narrative that the book was intended to target, and so, not only did she create those pages, but she also brought a business perspective to some of the narratives that came out in the book that was very helpful.”

The pair’s relationship works both ways with Belichick supporting Hudson during her adult cheerleading or pageant competitions.

“Roses 🆙 for Bill the WAG 💍🌹🌹🌹👌🏻,” she wrote via Instagram on April 26, teasing that Belichick was the male version of “Wife and Girlfriend” during her cheer meet.