As UPenn Bends the Knee, Keith Olbermann Can’t Stop Crying About Riley Gaines – Twitchy

Yesterday was a GIGANTIC win for reality, sanity, and protecting women’s sports from mediocre men. As Twitchy reported, the University of Pennsylvania, under pressure from the Trump administration, totally bent the knee to respecting Title IX and preventing men in womanface from competing against real women. 

Not only did UPenn issue a public statement that they will comply with Title IX and adopt biology-based criteria for who can compete, the school also vowed to restore all women’s records and championships that were erased by ‘Lia’ Thomas and strip Thomas of all of HIS medals. UPenn even agreed to issue a public apology to all female athletes who were impacted by their insanity. And even though the apology former UPenn swimmer Paula Scanlan received was lame and insincere, it was still a tremendous victory.

Naturally, this unequivocal vindication for all women made the left openly weep and rant. And who is better at weeping and ranting than Keith ‘Pee Tears’ Olbermann? 

The disgraced former ESPN and MSNBC host immediately turned to the woman with whom he is creepily obsessed to vent his rage.

Wanted to congratulate Whiny Gaines on now being able to say she finished tied for FOURTH not tied for FIFTH in the Lia Thomas race
(@Riley_Gaines_)

— Keith Olbermann (@KeithOlbermann) July 2, 2025

Riley Gaines just lives in his head 24/7, rent-free. It is sad and pathetic, but also hilarious, how weak he is. 

Naturally, Gaines took the opportunity to flatten Olbermann for what must be the umpteenth time. 

Thank you! And while you’re keeping track, make sure to congratulate Emma Weyant, the right National Champ in the 500 freestyle, too.

(If you’re insinuating 5th in the nation is bad, what do you call a man who ranks 462nd nationally in the men’s category?) https://t.co/liCRPraFQD

— Riley Gaines (@Riley_Gaines_) July 2, 2025

LOL. She simply owns him. 

(And yes, congratulations to the University of Virginia’s Emma Weyant, the ACTUAL champion in the 2022 women’s 500 freestyle, not some failed male swimmer with an autogynephilia fetish.)

We also love how sarcastically cordial Gaines is to Olbermann whenever he tries to come at her (which is only constantly). 

The rest of X was … not as nice. 

You really do hate us women don’t you? Well good, I hate you right back.

Stay in your man lane.

— Danielle (@daniellemerrim1) July 2, 2025

That’s awfully generous, calling Olbermann a ‘man.’ He may be male, but he clearly lacks any other qualities of a man. 

You’re a horrible excuse for a man.

— Dan H (@dalsx11) July 2, 2025

Yep. That’s more like it.

You have no children. No one in your life. You will die unloved and unmourned.

Congratulations.

— Bluesky Libs (@BlueskyLibs) July 2, 2025

OOF. 

We’d almost call that mean if it wasn’t so obvious and accurate. 

It is grossly ironic that one of the meanest, nastiest people around proudly rides his moral high horse thinking he has a shred of moral credibility. You genuinely bask in a consuming, smug hatred. How could you possibly think you help yourself with such bile? https://t.co/KRlSrdgj0U

— David Limbaugh (@DavidLimbaugh) July 2, 2025

As the previous post noted, Olbermann has no one in his life to tell him that he is an unhinged lunatic. 

He exists in a bubble of one. 

Just going to keep reposting this grown man who is so BIG mad that a young woman (@Riley_Gaines_ ) stood up for herself and her teammates and won.

It is truly creepy. https://t.co/wiw2mOJ2aM

— Carilyn Johnson (@CarilynJohnson) July 2, 2025

It is unbelievably creepy. We’d almost be concerned for Gaines’ safety, except we’re pretty sure she could take Olbermann with both arms tied behind her back. 

Hey Keith, why don’t you tell us all about your awards and titles in the various competitive sports that you’ve played.

I’ll wait.

— Rose of Sharon Mayer (@RozeRage) July 2, 2025

Zero. The answer is zero. And it shows. 

You are such a tool. I’ll say this though, you’re great at being both wrong and annoying!

— Jennifer Sey (@JenniferSey) July 2, 2025

Hey, everyone has to be good at something. 

Another female athlete — who was horribly injured by a man playing in her sport — said what we were all thinking. 

Dude stfu everyones begging

— Payton McNabb (@paytonmcnabb_) July 2, 2025

He should, but he can’t. His pathological obsession won’t allow him to. 

Your jealously heals the world.

— Queen Velvet (@TMIWITW) July 2, 2025

You’re the whiniest lesbian on this app, Keith.

— Dustin Grage (@GrageDustin) July 2, 2025

LOL. 

He does look like he is morphing into Rosie O’Donnell, doesn’t he? 

You should take your own advice, Keith. pic.twitter.com/mohsxsnEvt

— Matt Van Swol (@matt_vanswol) July 2, 2025

Whew. Tough crowd. 

But we are here for it because Olbermann deserves every bit of it and then some. 

You must be a really miserable person to pick on girls on the internet.

— Lorrie Ann 🇺🇲🇺🇲🇺🇸 (@LorrieAnn25) July 2, 2025

Fact check: True. 

Got it.

You, a sad excuse for a man, think it’s perfectly fine to marginalize biological women to satiate the desires and/or perversions of delusional men.

I had you pegged as a devout feminist.

But as it turns out, you’re actually a militant misogynist who ATTACKS women.

And…

— Bill Mc7 (@BillMc7) July 2, 2025

To the surprise of no one, Olbermann completely missed the point. 

None of this has anything to do with where Gaines — one of the most decorated female swimmers in American collegiate history — finished in her race against Thomas. 

It has to do with the fact that he never should have been allowed to compete against women in the first place. Not to mention that he shouldn’t have ever been permitted to share a locker room and expose himself to them. 

But Olbermann can’t see any of that because he is a creepy, broken shell of a human being who probably hates women so much because none of them will ever speak to him. 

You would fist yourself, but your hand hates you too.

— Andrew Wilkow (@WilkowMajority) July 2, 2025

Holy S***!  LOL.

And with that deadly, off-color parting shot, we are officially dead.

We will leave Keith Olbermann to wallow in his own crapulence until he decides to humiliate himself on X again.

We’re sure Riley Gaines will be ready for him.