Keith Olbermann unwisely took a jab at former NCAA swimmer Riley Gaines, host of "Gaines for Girls" on OutKick.com, over her athleticism. It didn't work out very well for him.
Olbermann, who has a history of going after prominent conservative-leaning women on social media from the safety of his basement studio, opted to take a shot at Gaines after Education Secretary Linda McMahon suggested she would have won her race had it not been for a biological male participating in the event.
"She finished 85th in the Olympic Trials," he responded. "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] was, somehow, a worse swimmer than she is a MAGA stooge."
Nerds taking on superior athletes rarely work out. And Olbermann drew a response from Gaines. She might as well have given him an atomic wedgie, a swirly, and stuffed him in a locker.
Gaines defended herself by pointing out she was just 15 when she competed in the Olympic trials.
"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?" she wondered.
"No. You’re just a misogynistic pig [and] an old, deranged man with a terminal case of TDS who can’t hold down a job."
I placed 85th at Olympic trials when I was 15/16? I was one of the youngest there.
— Riley Gaines (@Riley_Gaines_) May 28, 2025
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… https://t.co/CMsHINKRPz
RELATED: Keith Olbermann Diagnosed With Terminal Trump Derangement Syndrome
All of which is true.
Keith, whose podcast rants make him seem about as well-connected to reality and mature as Harry Sisson, has been fired and/or suspended from Fox Sports, Current TV, ESPN (multiple times), and MSNBC/NBC.
Literally can't hold down a job.
Gaines then told Fox News Digital that Olbermann should put his money where his mouth is and compete against her in a charity race. Initially, she was hesitant to engage in such a challenge for reasons that made sense to anybody with a working pair of eyes.
"I'd challenge [Keith] to a race where the loser puts up $ to the charity of the winner's choice, but no one wants to see him in a Speedo," she said.
That said, she eventually relented and opted to see if Olbermann was interested in a 200-yard freestyle for a good cause. The former sports journalist dusted off his potato chip-greased hands, pulled up his little Handmaid's Tale underoos, and marched right back down to his basement to respond by tweet.
"This is a brilliant idea [Riley]! A 66-year-old man with an arthritic left knee and chronic stress fractures in the right foot," he wrote. "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
Bro, who are you kidding? Even in your prime, there is zero chance you'd have a shot against Joe Biden in a bike race, let alone Riley freaking Gaines in a swimming competition.
Gaines is an accomplished former NCAA swimmer. Her bio at Kentucky recounts a slew of academic and athletic accomplishments, including:
- 2021, 2022 All-SEC First Team
- 2022 SEC Female Scholar-Athlete of the Year
- One of the most decorated swimmers in program history
Olbermann, by contrast, mostly likes to rant at the clouds and has never played a sport in his life. The one time he actually tried to pull off an athletic feat of any kind was in 1980 when, upon watching a Mets game at the old Shea Stadium, he tried leaping onto a subway only to hit his head so hard that it rendered him unable to drive a vehicle.
Keith must enjoy getting smacked around by strong women. The completely unemployable has-been once took on Megyn Kelly by pointing to a job controversy during her time at NBC News. And again, it didn't turn out well for him.
Love this more than I can say. pic.twitter.com/JMdaLzbkOa
— James Woods (@RealJamesWoods) April 28, 2023
“But the record is very clear that I left voluntarily because I wanted to raise my family,” Kelly replied. “Something you don’t know anything about because no one would marry you.”
“And you have no children,” she continued. “You have a cold, lonely life in which you’ve become a bitter, bitter man."
Now, he's a bitter, deranged man shouting into the wind, desperately trying to get the attention of a young woman with athletic prowess and the intellect to understand when a man is pretending to be a woman to improve their athletic careers.
All because he has none of those attributes.
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