Riley Gaines, the former collegiate swimmer (University of Kentucky) who became a Trump supporter and conservative political activist while campaigning against the participation of trans women in women’s sports, challenged liberal political commentator Keith Olbermann to a race for charity.
After Olbermann dissed Gaines on X, noting that “she finished 85th in the Olympic Trials” and “finished tied for 5th in the only race including a transgendered athlete,” Gaines replied to Olbermann with a challenge “to a race where the loser puts up $ to the charity of the winners [sic] choice, but no one wants to see him in a speedo.”
Olbermann continued the banter by replying: “This is a brilliant idea @Riley_Gaines_ ! A 66-year old man with an arthritic left knee and chronic stress fractures in the right foot… Somebody you could finally beat!”
This is a brilliant idea @Riley_Gaines_ !
— Keith Olbermann (@KeithOlbermann) May 29, 2025
A 66-year old man with an arthritic left knee and chronic stress fractures in the right foot…
Somebody you could finally beat! pic.twitter.com/jCP05RiihN
He added: “I will give @Riley_Gaines_ this: She really is an Olympic-level champion of excuses, whining, and self-martyrdom.”
In February, the U.S. Department of Health and Human Services (HHS) released a video of Gaines talking about her role helping with Trump’s Executive Order, which threatens to revoke federal funding from any elementary, secondary, and post-secondary institution that allows transgender girls to play on girls’ teams.
Note: According to the NCAA, only 10 athletes of the 530,000 in the NCAA’s association of student-athletes identify as trans.
Over the weekend the contentious issue received fresh fuel as the LA Times reports that 16-year-old transgender athlete AB Hernandez, competing in the girls events, “bounded past many of her peers to win multiple gold medals at California’s high school track and field championships Saturday.”
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