Bill Belichick and his age-gap relationship with Jordon Hudson have drawn online scrutiny for years. SNL alum Shane Gillis also didn’t miss a chance to jump into the trending discussion. He took a playful jab at the legendary football coach and his 49-year-younger girlfriend during one of his roasting sessions. Shane linked an ongoing gambling controversy to Bill’s relationship with Jordon and made some debatable remarks about the couple.
Shane Gillis took a jab at Bill Belichick and his girlfriend, Jordon Hudson
Bill Belichick and Jordon Hudson’s 48-year age gap has consistently sparked curiosity about their dynamic. Shane Gillis once took a savage dig at the couple during his monologue at the ESPYs 2025. At that time, MLB star Shohei Ohtani was under intense scrutiny for his former interpreter’s gambling scandal. Regarding him, Shane said, “Shohei is a once-in-a-generation talent. No one has been able to do what he does at so many positions: pitcher, hitter, and bookie.”
Shane Gillis then linked the controversy with Bill Belichick and Jordon Hudson, saying, “A bookie is what Bill Belichick reads to his girlfriend before bedtime.” Shane turned the monologue’s focus on the age difference between the couple and jovially stated, “They do. They read The Very H—y Caterpillar, The Little Engine That Could But Needed a Pill First, and of course, the classic Goodnight B—s.”
The live audience burst out laughing at Shane’s comment, following which he clarified that he wasn’t “trashing” Bill. Mentioning the age of the former New England Patriots coach, Shane sarcastically called the audience out by asking why they were mocking a talented man for having a young and “hot” girlfriend.
Shane then delivered the final blow, saying that no one seated in the audience would be with their “fat, ugly dog wife” if they were as talented as Bill Belichick. Many found the comment offensive and misogynistic, and the stand-up comedian faced backlash. His exact words were:
“First off, he’s 73 years old [now 74], and he’s dating a hot 24-year-old [now 25], and people are criticizing him. What happened to this country?… We used to be a great country. He won six Super Bowls. He’s dating a hot 24-year-old. Maybe if you guys won six Super Bowls, you wouldn’t be sitting next to a fat, ugly dog wife.”
More about Bill Belichick and Jordon Hudson
Bill Belichick and Jordon Hudson reportedly met for the first time in February 2021 when they were seated next to each other on a flight. While they were flying from the Boston area to Florida, Bill signed one of Jordon’s textbooks and reportedly also wrote, “Thanks for giving me a course in logic!” Although Bill and Jordon’s first meeting dates back to 2021, the couple weren’t linked until January 2023.
At the time, Bill and Jordon were reportedly seen walking through the French Quarter in New Orleans. A few months after their public sighting, the pair were spotted for the second time in September 2023, enjoying a dinner date in the city. In June 2024, TMZ was the first to confirm that Bill Belichick and Jordon Hudson were in a romantic relationship.
In December 2024, Bill and Jordon made their red carpet debut as a couple at the Museum Gala in New York City. Jordon shared her thoughts on the event, saying it was filled with all her favorite things, including her “Billy.”
What are your thoughts on Shane Gillis’ jabs at Bill Belichick and his girlfriend, Jordon Hudson? Let us know.
Photo courtesy: Jordon Hudson/Instagram
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