Conservative activist Riley Gaines has challenged former ESPN host Keith Olbermann to a race after he hit out at her for her support of Donald Trump.
Gaines tied for fifth place with University of Pennsylvania swimmer Lia Thomas, a biological male, in 2022 while swimming for the University of Kentucky in the 200-yard NCAA freestyle championship.
The 25-year-old has since been outspoken against transgender athletes competing in women’s sport, haling the president for his ‘Keeping Men Out of Women’s Sport’ executive order earlier this year.
This week, Olbermann, the ex-host of both MSNBC’s ‘Countdown with Keith Olbermann’ and ESPN’s ‘SportsCenter,’ took aim at the former collegiate swimmer over her campaigning.
Olbermann responded to a Fox News clip of Education Secretary Linda McMahon claiming that Gaines ‘would have clearly won’ her race if Gaines didn’t have to compete against transgender athlete Thomas.
‘[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.’
Gaines, a 12-time NCAA All-American, fired back at the sports commentator, noting she ‘placed 85th at Olympic trials when I was 15/16.’

Conservative activist Riley Gaines has challenged former ESPN host Keith Olbermann to a race
In 2022, Gaines tied for fifth with transgender swimmer Lia Thomas (pictured left)
‘I was one of the youngest there,’ Gaines explained. ‘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 just a misogynistic pig & an old, deranged man with a terminal case of TDS who can’t hold down a job.’
She went on to challenge Olbermann to back up his criticism by taking her on in a race for charity, Gaines told Fox Digital.
She said that the event would be a 200-yard freestyle at a location of Olbermann’s choice sometime before August 31 with proceeds going to a charity of the winner’s choosing.
Olbermann appeared to accept the challenge, branding the competition a ‘brilliant idea.’
‘A 66-year old man with an arthritic left knee and chronic stress fractures in the right foot… Somebody you could finally beat!’ he taunted in response to the challenge.
The heated online tiff comes after Gaines joined many in expressing outrage over a transgender athlete competing in girls’ high school track and field in California.
AB Hernandez of Jurupa Valley, a biological male, won the women’s long jump and triple jump at the California Interscholastic Federation Southern Section Masters Meet last week.
Reese Hogan of Crean Lutheran High School, one of the opponents defeated by Hernandez, took the podium following the official ceremony.
The 25-year-old has been outspoken against trans athletes competing in women’s sport
AB Hernandez of Jurupa Valley is making waves in track and field in contentious fashion
Last week one of Hernandez’s beaten opponents waited to take her spot at the top of a podium
The moment took off online, and earned praise from Gaines. In March, Hernandez drew backlash online after winning a triple jump event by three feet.
In response to the backlash, Trump blasted California governor Gavin Newsom , who he called ‘Newscum,’ and called a transgender athlete’s sporting domination in the state ‘not fair and totally demeaning to women and girls.’
‘Please be advised that large scale federal funding will be held back, maybe permanently,’ Trump threatened on his Truth Social site.
Then, without citing a specific legal basis, Trump wrote that ‘I am ordering local authorities, if necessary, to not allow the transitioned person to compete in the State Finals. This is a totally ridiculous situation!!!’
Gaines has been vocal in her opposition to allowing trans athletes to compete in women’s sport and has dedicated the past two years to campaigning on the issue.
She was invited to Trump’s address to Congress in March when the president turned his focus to keeping trans athletes out of women’s sports.
The subject had been a big driving force in his election last November and Trump elected to highlight the story of Payton McNabb, a former high school volleyball player who was left with brain damage after being spiked in the face by a trans opponent, during his speech.
Trump had previously surrounded himself with female athletes and activists, including Gaines, at the White House a month earlier to sign an executive order barring trans participation in women’s sports.
The order uses Title IX, a law against sex discrimination in taxpayer-funded education programs, to ban transgender girls and women from participating in female school sports activities.