After Former ESPN Host’s Public Insult, Riley Gaines Demands Swim-Off to Settle the Score

Riley Gaines, former NCAA swimmer and outspoken advocate for women’s sports, officially challenged ex-ESPN and MSNBC host Keith Olbermann to a charity swim race on Wednesday, as reported by Fox News.

The move came after Olbermann mocked her athletic record and called her a “MAGA stooge.”

The exchange began when Olbermann responded to a Fox News segment in which Education Secretary Linda McMahon said Gaines “would have clearly won” her NCAA race if not for having to compete against transgender swimmer Lia Thomas.

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Olbermann posted on X, “[Riley Gaines] finished 85th in the Olympic Trials. She finished tied for 5th in the only race including a transgendered athlete. If there had been none she MIGHT have finished tied for 4th, or had 5th place to herself.”

Gaines, a 12-time NCAA All-American and former University of Kentucky swimmer, responded by clarifying that she placed 85th at the Olympic Trials when she was just 15 or 16 years old.

“I was one of the youngest there,” she wrote. “And I placed 5th in the nation in a sport measured in .01s of a second without going a best. Would you say the 5th best college football player is objectively bad at their sport?”

I placed 85th at Olympic trials when I was 15/16? I was one of the youngest there.

And I placed 5th *in the nation* in a sport measured in .01s of a second without going a best. Would you say the 5th best college football player is objectively bad at their sport?

No. You’re… https://t.co/CMsHINKRPz

— Riley Gaines (@Riley_Gaines_) May 28, 2025

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Following her response, Gaines told Fox News Digital she is now challenging Olbermann to a charity race—a 200-yard freestyle at a location of his choice, to take place before August 31.

She offered him a handicap option of swimming 150 yards if that would incentivize him to accept. The winner would choose the charitable organization to receive the proceeds.

A spokesperson for Olbermann did not respond to Fox News Digital’s request for comment.

The challenge comes as the broader debate around transgender participation in women’s sports continues. This week, the California Interscholastic Federation (CIF) approved a transgender athlete’s participation in an upcoming women’s state track championship.

President Donald Trump responded on Truth Social, writing: “California, under the leadership of Radical Left Democrat Gavin Newscum, continues to ILLEGALLY allow ‘MEN TO PLAY IN WOMEN’S SPORTS.’”

Image Credit: Shutterstock

Trump added that the athlete in question “won ‘everything’” and is now qualified for the state finals.

Trump also pointed to his February 5 executive order banning male athletes from competing in women’s sports. He warned that California could lose federal funding if the state fails to comply.

“THIS IS NOT FAIR, AND TOTALLY DEMEANING TO WOMEN AND GIRLS,” the president posted. “Please be hereby advised that large scale Federal Funding will be held back, maybe permanently, if the Executive Order on this subject matter is not adhered to.”

California Governor Gavin Newsom’s office released a statement supporting the athlete’s right to compete.

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