Comedian Shane Gillis ignited a flurry of reactions at the 2025 ESPY Awards with a monologue that pulled no punches, targeting an array of sports legends and public figures. From the start, his style was reminiscent of roast comedy, challenging the boundaries of the traditional awards show opener. The audience at the Dolby Theatre in Los Angeles was met with biting humor directed toward notable names, with Gillis swiftly honing in on New England Patriots legend Bill Belichick and his 24-year-old girlfriend, Jordon Hudson. One of his more memorable lines was, “A bookie is what Bill Belichick reads to his girlfriend before bedtime,” setting a raucous—and for some, uncomfortable—tone as he detailed fictitious amusing book titles supposedly shared between the pair.

Reactions to Gillis’ performance were as diverse as his targets. Social media users quickly voiced polarized views, with some lauding his no-holds-barred approach to satirizing the sports elite, and others decrying what they perceived as punchlines crossing lines of taste or decency. During his monologue, the comedian also poked fun at a string of athletes and personalities, including Simone Biles, Caitlin Clark, and Aaron Rodgers, ensuring that nearly every corner of sports culture was fair game for his sharp wit. In particular, a joke about Caitlin Clark’s hypothetical post-basketball career and jabs at Rodgers’ vaccine skepticism received a smattering of both laughs and noticeable silence, reflecting the audience’s divided response.

Perhaps the most headline-grabbing moments involved Gillis’ material about former President Donald Trump. With references to Trump’s supposed desire to host a UFC fight on the White House lawn and to recalcitrant former Vice President Mike Pence, Gillis’s routine blended topical political references with sports celebrity humor. He quipped about Trump’s involvement with sports, joking, “Donald Trump wants to organize a UFC match on the lawn of the White House. The last time he organized a fight in D.C., Mike Pence nearly met his end,” drawing a mix of laughter and discomfort in equal measure. Gillis also included an impersonation of Trump and linked his jokes to other pop culture figures such as Joe Rogan and NBA Commissioner Adam Silver.

The monologue did not shy away from addressing even more sensitive subjects, including a contentious bit about the Jeffrey Epstein files, which Gillis cleverly sidestepped by suggesting the joke had “deleted itself,” prompting both awkward laughter and murmurs throughout the venue. As boos and cheers traded places in the crowd, Gillis maintained his composure, even inviting the audience to “lighten up” mid-set. Online, the discourse continued, with some fans praising his fearlessness while critics questioned the appropriateness of the event’s tone under his stewardship. Gillis’s unwavering approach undeniably left a mark, ensuring the conversation around the 2025 ESPYs would linger far beyond the night.