Shane Gillis both roasts and defends Bill Belichick during ESPYs monologue

We all saw this coming, right?

When comedian Shane Gillis was announced as the host of this year’s ESPY Awards, it was clear as day that 73-year-old Bill Belichick was going to catch at least one stray during the opening monologue for very publicly dating the much-discussed 24-year-old Jordon Hudson.

Has there ever been fruit hanging lower than this one?

And just over four minutes into his opening segment, Gillis got to his Belichick material by way of Shohei Ohtani material:

“Shohei Ohtani couldn't make it tonight. Man, I hope his interpreter didn't bet that he was going to be here…

“Shohei is a once in a generation talent. No one's been able to do what he does at so many positions. Pitcher, hitter and bookie…

“A ‘bookie’ is what Bill Belichick reads to his girlfriend before bedtime…

“They do - they read ‘The Very Horny Caterpillar,’ ‘The Little Engine That Could, But Needed a Pill First,’ and of course the classic ‘Goodnight, Boobs’ …"

On the tail end of those jokes, Gillis went into a mini rant defending Belichick for dating someone 49 years his junior.

Shane Gillis
Shane Gillis at the 2025 ESPY Awards held at the Dolby Theatre on July 16, 2025 in Los Angeles, California. Photo credit Christopher Polk/Getty Images

“Also, I'm not trashing Bill Belichick,” said Gillis. “First off, he's 73 years old. He's dating a hot 24-year-old, and people are criticizing him. What happened to this country? It used to be a great country.

“He won six Super Bowls. Yeah, 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.”

That last part played pretty poorly to the room, to which Gillis said, “They let me do it. I don’t know - Disney, they allowed that.”

It’s not the first time Belichick has been the butt of the joke for his dating life, and it certainly won’t be the last.

So long as Hudson is in the picture - and almost certainly for many years after she’s no longer in the picture - the punchlines surrounding Belichick will be persistent.

Bill Belichick and Jordon Hudson
Bill Belichick, Jordon Hudson at the 14th Annual NFL Honors held at Saenger Theatre on February 06, 2025 in New Orleans, Louisiana. Photo credit Christopher Polk/Variety/Getty Images

Belichick, who was in the news on Wednesday for taking on-the-record shots at Patriots owner Robert Kraft, will open his first season as head football coach at North Carolina with a standalone, primetime game against TCU on Labor Day.

Kickoff is scheduled for 8:00 p.m. ET on ESPN.

Featured Image Photo Credit: Christopher Polk/Getty Images