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Shane Gillis, Bill Belichick and Donald Trump

Shane Gillis stirs controversy with Trump, Bill Belichick jokes during edgy ESPY Awards monologue

Gillis didn’t stop there with the Trump mentions, as he poked fun at the 47th president for recently saying he wants to stage a UFC fight at the White House.

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ESPYS 2025: Shane Gillis Roasts Bill Belichick and Jordon Hudson With Age-Gap Jokes

· 21h · on MSN

Shane Gillis’ edgy ESPY monologue divides, takes shots at Donald Trump, Caitlin Clark, Bill Belichick

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Simone Biles wins two ESPY awards as Shane Gillis' tough monologue grabs attention

Simone Biles won two trophies at the ESPYS on Wednesday night, including the women’s best athlete award.

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Best Fan Tweets, Memes to Shane Gillis' Opening Speech at 2025 ESPY Awards

· 20h

Shane Gillis’ 10 Best Jokes at the ESPY Awards (Critic’s Picks)

· 1d

Simone Biles wins two ESPYS, beating out Stephen Curry, Freddie Freeman and Rory McIlroy

She won three golds and a silver while helping the U.S. women's gymnasts win their first team title since 2016.

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Shane Gillis drops Epstein joke during host monologue at ESPYs

· 1d

Shane Gillis Faces Backlash for His Caitlin Clark Joke in 2025 ESPYs Monologue

20hon MSN

Shane Gillis Struggles for Laughs in 2025 ESPYS Monologue as He Mocks Simone Biles, Jordon Hudson

Comedian Shane Gillis roasted sports' biggest stars while battling boos and silence from the Dolby Theater audience during his monologue at the 2025 ESPYS on Wednesday, July 16.

“Goodnight Boobs”: Shane Gillis roasts Bill Belichick reads raunchy bedtime stories to 24-year-old girlfriend at ESPYs

Shane Gillis targeted Bill Belichick at the ESPYs. Gillis joked about Belichick's relationship with Jordon Hudson. The jokes referenced their age gap.

14hon MSN

Bill Belichick, Jordon Hudson romance brought up at ESPYs

Bill Belichick and Jordon Hudson's relationship was joked about at the 2025 ESPYs by its host, Shane Gillis. Bill Belichick and Jordon Hudson were roasted at the 2025 ESPYs despite not attending the event on Wednesday, July 16.

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Caitlin Clark

ESPY Award