Although the ESPYS are all about recognizing outstanding achievements in sports, the post-award show discourse seems to be centered on Shane Gillis’ headline-grabbing monologue — not the athletes. The actor and stand-up comedian did not hold back during the opening 10 minutes, taking jabs at everyone from WNBA superstar Caitlin Clark to that dusty old Cheeto in the White House, D*nald T*ump. While several of Shane’s sports and politics jokes did land with the crowd, other moments in the monologue were met with groans, awkward silence, and even some boos. (I fear I had Jo Koy Golden Globes monologue-flavored déjà vu there for a sec.)

The day after the award show, TODAY’s Carson Daly offered his take on the polarizing monologue: “He had a lot of jokes that were really hilarious, then he had a lot of jokes like, ‘Oh my gosh, I can’t believe he just said that.’ It sort of ran the gamut there.” The TV host added, “It was awkward.” So, why was Shane’s ESPYS monologue so controversial? Let’s take a look at the jokes Shane Gillis made about Caitlin Clark, Bill Belichick and Jordon Hudson, Trump, the Epstein files debacle, and more.

Shane Gillis’ Controversial ESPYS Monologue: Video, Jokes Breakdown

Why Was Shane Gillis’ ESPYS Monologue Controversial? Caitlin Clark, WNBA Jokes

Shane Gillis’s full ESPYS monologue

What was your favorite joke? 🤔 pic.twitter.com/XdaRwjYQK0

— Dov Kleiman (@NFL_DovKleiman) July 17, 2025

Honestly, I thought Shane’s political jokes were pretty funny (though the subject matter is obviously depressing AF). “There’s supposed to be an Epstein joke here, but I guess it got deleted,” he said, referencing the T*ump administration’s extremely odd handling of the Epstein files. “Probably deleted itself, right? Probably never existed, actually. Let’s move on.” He also alluded to the 2021 insurrection incited by the president. “Donald Trump wants to stage a UFC fight on the White House lawn,” Shane said. “The last time he staged a fight in D.C., Mike Pence almost died.” LOL.

I also thought the comedian’s Bill Belichick age gap relationship joke was a highlight. After making a bookie joke about Dodgers player Shohei Ohtani, he quipped: “A bookie is what Bill Belichick reads to his girlfriend before bedtime. They read, Very Horny Caterpillar. The Little Engine That Could But Needed A Pill First, and of course, the classic, Good Night Boobs.” The audience seemed to appreciate that one, though I’m sure Bill and his GF are fuming somewhere out there.

Unfortunately, the Caitlin Clark and WNBA jokes were a bit cringe. “When Caitlin Clark retires from the WNBA, she’s going to work at a Waffle House so she can continue doing what she loves most: fistfighting Black women,” Shane said. The audience laughed a little, but there were definitely some groans. (He was likely referencing the basketball star’s involvement in physical play against Black athletes like Angel Reese and Chennedy Carter.)

He also tried to roast the popularity level of the WNBA, which is just tired and annoying, TBH. “Four-time WNBA All-Star Brittany Hicks is here,” Shane said. “Give it up for Brittany, everybody. I’m joking around. That’s my friend’s wife. I knew none of you knew WNBA players.”

Will Shane be invited back to host next year? TBD.