ESPYS Host Mocks Belichick’s Romance with Jordon Hudson
Another evening at the ESPYS and we have a new blockbuster: Bill Belichick’s personal life under the comedy microscope. At the 2025 ESPY Awards, comedian and ceremony host Shane Gillis zeroed in on the 48-year age gap between the 73-year-old NFL coaching legend and his 24-year-old girlfriend, Jordon Hudson. As first reported by E! Online and picked up by ESPN’s awards coverage, Gillis delivered a string of NSFW bedtime “reads” that left the audience squirming with laughter.
Gillis kicked off his monologue by declaring, “A bookie is what Bill Belichick tucks his girlfriend in with each night.” He then rattled off a fictional library of bedtime classics: The Very Horny Caterpillar, The Little Engine That Could But Needed a Pill First, and his personal favorite, Goodnight Boobs. The rapid-fire quips were laced with absurdity yet delivered in a disarmingly calm tone that only heightened the comedic punch.
True to deadpan form, Gillis paused to clarify that he wasn’t out to vilify Belichick. “He’s 73 and dating a hot 24-year-old, and people are upset? What happened to this country?” he quipped, before adding a caveat only an NFL fanatic could appreciate: “He won six Super Bowls. Maybe if you had a ring or two, you could chase tail too.” That blend of mock sympathy and grudging respect echoed through the crowd, which included both Belichick and Hudson in the front row.
This roast wasn’t entirely unprecedented. Back in February at the NFL Honors, Snoop Dogg also took a playful swipe at the pair. During his opening monologue, he reminisced about “when the Cowboys were good” and “when the Chiefs were bad,” before trailing off with a dramatic pause: “What was it—Bill Belichick’s girlfriend wasn’t even born yet?” That zinger, covered by People Magazine, earned a hearty chuckle from Belichick and a stunned-look-then-laugh from Hudson.
The social media reaction kept the fun going. When Hudson shared a beach photo on X—formerly Twitter—of Belichick hoisting her up in an “airplane” game, ESPN’s Mina Kimes couldn’t resist a jab. “My 18 month old loves this game,” she wrote, prompting users to point out that her daughter is 38 years younger than the reporter, but Belichick’s partner is a full 48 years his junior. The post went viral, racking up millions of views and reigniting the conversation about May-December relationships in the sports world.
Despite the teasing, Belichick and Hudson have taken the attention in stride, attending events together and even sharing inside smiles at pointed jokes. Their dynamic continues to fascinate fans who can’t decide whether to applaud the power balance or question the headlines. Meanwhile, the ESPYS rolled on with other memorable moments: Shai Gilgeous-Alexander’s surprising acceptance speech, Russell Wilson and Ciara’s coordinated red-carpet look, Simone Biles sharing laughs with Jonathan Owens, and a touching performance by Tobe Nwigwe alongside his brother Fat Nwigwe.
In a showdown of jokes versus legacy, Gillis showed that in today’s sports awards circuit, even legends aren’t off limits. Tune in next time for more awkward punchlines and trophy-shaped cake catastrophes.
Sources: Celebrity Storm and E! Online, ESPN
Attribution: Creative Commons Licensed
