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Riley Gaines Challenges Keith Olbermann to Charity Swim Race

Christopher Blake May 29, 2025
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Former ESPN and MSNBC host Keith Olbermann and former NCAA swimmer Riley Gaines are engaging in a public dispute, sparked by Olbermann’s comments regarding Gaines’ swimming abilities and her political views.

Olbermann criticized Gaines on social media, referencing her performance in the Olympic Trials and her stance on transgender athletes in women’s sports.

Gaines, a vocal advocate against transgender women competing in women’s sports, responded to Olbermann’s remarks and challenged him to a 200-yard freestyle race for charity.

Gaines has proposed that the winner of the race would select the charitable organization to receive the proceeds from the event.

The race would be held before August 31st, at a location chosen by Olbermann; Gaines is open to adjusting the distance to incentivize his participation.

Olbermann’s comments came after Education Secretary Linda McMahon commented on the impact of transgender athlete Lia Thomas’ participation on Gaines’ race results.

Gaines’s initial Olympic Trials performance was also a topic of discussion, with differing interpretations of her results.

The debate takes place amidst broader discussions about transgender athletes in sports, including former President Donald Trump’s stance and an Executive Order on the matter.

Trump has criticized California’s policies on transgender athletes, threatening to withhold federal funding if the state doesn’t comply with his views.

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