Conservative activist Riley Gaines has challenged former ESPN host Keith Olbermann to a charity swimming race following a heated online exchange over transgender athletes in women's sports.
The confrontation began when Olbermann criticised Gaines for her support of Donald Trump and questioned her swimming credentials.
Gaines, who tied for fifth place with transgender swimmer Lia Thomas at the 2022 NCAA freestyle championship, has become a prominent voice against biological males competing in women's sport.
The 25-year-old former University of Kentucky swimmer has campaigned extensively on the issue since her collegiate career ended.
Riley Gaines has challenged Keith Olbermann to a charity swimming race
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The dispute escalated when Olbermann responded to comments from Education Secretary Linda McMahon suggesting Gaines would have won her race without transgender competition.
Olbermann, the former host of MSNBC's "Countdown with Keith Olbermann" and ESPN's "SportsCenter," took aim at the former collegiate swimmer over her campaigning.
He responded to a Fox News clip featuring Education Secretary Linda McMahon's claims about Gaines' performance.
"[Riley Gaines] finished 85th in the Olympic Trials," Olbermann posted on X. "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."
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She 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 @Riley_Gaines_ was, somehow, a worse swimmer than she is a MAGA stooge https://t.co/ghynITGk6s
— Keith Olbermann (@KeithOlbermann) May 28, 2025
The comments appeared designed to undermine Gaines' credibility as a spokesperson on transgender participation in women's sport.
Olbermann's criticism focused on her Olympic Trials placement and suggested her NCAA championship performance was unremarkable.
Gaines, a 12-time NCAA All-American, fired back at the sports commentator with a robust defence of her achievements.
She noted: "I placed 85th at Olympic trials when I was 15/16" and explained: "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," Gaines continued.
"Would you say the 5th best college football player is objectively bad at their sport?"
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Gaines subsequently challenged the former broadcaster to back up his criticism by competing against her in a swimming race for charity.
The proposed event would be a 200-yard freestyle at a location of Olbermann's choice before August 31st.
Olbermann appeared to accept the challenge, branding the competition a "brilliant idea." The 66-year-old former broadcaster acknowledged his physical limitations whilst taunting his potential opponent.
"A 66-year old man with an arthritic left knee and chronic stress fractures in the right foot... Somebody you could finally beat!" he wrote in response to the challenge.
Despite these apparent disadvantages, Olbermann seemed willing to participate in the charitable contest.
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Keith Olbermann had previously criticised Riley Gaines' support of Donald Trump
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The race proceeds would go to a charity of the winner's choosing, with the total wager amount to be determined if Olbermann formally agrees.
Gaines told Fox Digital that she would even allow Olbermann to swim a shorter 150-yard freestyle whilst she completed the full 200 yards to incentivise his participation.
The challenge comes amid broader controversy over transgender participation in women's sport, particularly following President Trump's executive order banning biological males from competing in female categories.
Trump signed the order on February 5th using Title IX legislation to bar transgender girls and women from participating in female school sports activities.
Recent events in California have intensified the debate, with transgender athlete AB Hernandez winning women's long jump and triple jump at the California Interscholastic Federation Southern Section Masters Meet.
Trump threatened to withhold federal funding from California, posting on Truth Social: "Please be advised that large scale federal funding will be held back, maybe permanently."
Gaines has been vocal in her opposition and was invited to Trump's congressional address in March when the president highlighted the issue.
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