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Riley Gaines Challenges Keith Olbermann to Charity Swim Race

Christopher Blake May 29, 2025

Former ESPN and MSNBC host Keith Olbermann made comments on social media criticizing swimmer Riley Gaines, leading to a public challenge.

Olbermann’s comments, posted on X, included remarks about Gaines’ swimming ability and political affiliations. He was responding to a post by Education Secretary Linda McMahon regarding Gaines’ races against transgender swimmer Lia Thomas.

Gaines, a 12-time NCAA All-American, responded to Olbermann’s remarks on X, defending her athletic achievements and performance at the Olympic Trials.

Gaines has formally challenged Olbermann to a 200-yard freestyle race for charity, with the winner selecting the beneficiary and the total donation amount to be determined upon Olbermann’s agreement.

The race is proposed to take place before August 31st at a location chosen by Olbermann.

Olbermann’s spokesperson has not yet provided a comment on the challenge.

The exchange between Gaines and Olbermann occurred amidst ongoing debate regarding transgender athletes in sports.

Former President Donald Trump weighed in on the issue, criticizing California Governor Gavin Newsom’s stance on allowing transgender athletes to compete in women’s sports.

Trump posted on Truth Social, expressing disapproval of transgender athletes competing in women’s sports and suggesting potential withholding of federal funding if the state doesn’t comply with an executive order on the matter.

California Governor Newsom’s office has released a statement supporting the participation of the transgender athlete in the upcoming state championship.

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