Joshua Goldman
Joshua Goldman
min read · July 17, 2025 · Entertainment

Shane Gillis Shocks ESPYs with Controversial Trump and Epstein Jokes

Shane Gillis pushed the limits with his opening monologue at the 2025 ESPYs

SCANDAL ROCKS THE ESPYS: Comedian Shane Gillis Shocks A-list Crowd with Insulting Jokes About President Trump, Caitlin Clark, and Bill Belichick's 24-year-old Girlfriend!

The highly anticipated ESPYs ceremony took a dramatic turn on Wednesday night when comedian Shane Gillis brought the house down with his scathing jokes about President Donald Trump, WNBA star Caitlin Clark, and New England Patriots head coach Bill Belichick's rumored girlfriend, Jordon Hudson.

Gillis, known for his spot-on impersonations of Trump, did not hold back as he took aim at the president's handling of the Jeffrey Epstein scandal. "There was supposed to be an Epstein joke here, but I guess it got deleted... probably deleted itself, right? Probably never existed, actually. Let's move on as a country and ignore that," he said, leaving the star-studded audience in stunned silence.

Druski was left stunned by Gillis' jokes during his opening monologue on Wednesday

But that wasn't the only bombshell dropped by Gillis during his opening monologue. He also took a swipe at Trump's attempt to stage a UFC fight on the White House lawn, quipping, "The last time he staged a fight in D.C., Mike Pence almost died."

Gillis didn't stop there, however. The comedian also went after Caitlin Clark, saying that when she "retires from the WNBA, she's going to work at a Waffle House so she can continue doing what she loves most: fist-fighting black women." He then compared himself to Clark, stating, "We're both whites from the Midwest who have nailed a bunch of threes."

But perhaps the most shocking joke of the night came when Gillis took aim at Bill Belichick and his 24-year-old girlfriend. "Shohei is a once-in-a-generation talent. No one's been able to do what he's done at so many positions - pitcher, hitter, and bookie," he said, referencing the $17 million betting scandal involving Belichick's former interpreter. "Bookie" is what Bill Belichick reads to his girlfriend before bedtime, he continued, drawing rapturous laughter from the crowd.

Gillis walked the red carpet with his girlfriend Grace Brassel on Wednesday

The comedian didn't let up there, however. He went on to say that Belichick is 73 years old and dating a hot 24-year-old, and that people are criticizing him for it. "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," he said, leaving the audience in shock.

Gillis also took aim at Dodgers star Shohei Ohtani, saying that he's "a once-in-a-generation talent... no one's been able to do what he's done at so many positions - pitcher, hitter, and bookie." He then compared Olympic gymnast Simone Biles to a leprechaun, saying that she's 4'8" and has seven gold medals. "When she's not competing, she leads a very quiet life at the base of a rainbow. If you tell Simone a riddle and she can't answer, she has to give you all her gold," he cracked.

The ESPYs ceremony drew a who's-who crowd to the Dolby Theatre in Hollywood, including Giants quarterback Russell Wilson and his singer wife Ciara, US women's soccer icon Alex Morgan, NBA legend Oscar Robertson, former star fighter Sugar Ray Leonard, Terrell Owens, Biles' Olympic teammate Suni Lee, and more.

It's clear that Shane Gillis left it all on the stage at the ESPYs - and we can't get enough of his hilarious (and sometimes shocking) jokes! Stay tuned for more updates from the ceremony, and don't forget to follow @thescholarlynote.com for all your celebrity news and gossip needs!

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The comedian also took aim at President Donald Trump and the January 6 riots

Gillis brought up late convicted sex offender Jeffrey Epstein in his opening monologue

Kyle Juszczyk, Kristin Juszczyk, Simone Biles, Jonathan Owens at the 2025 ESPY Awards

Russell Wilson and Ciara are seen on the red carpet for the ESPYs on Wednesday

Fellow NFL quarterback Matthew Stafford and his wife, Kelly, were also in attendance