Warning to the Woke: The Sad State of Keith Olbermann is How it Ends

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If you didn’t bother to see why Keith Olbermann resurfaced in the news this week, let me fill you in: After Barstool Sports commemorated high schooler Tate Myre, who gave his life to protect fellow students during a Michigan school shooting, Olbermann, via the quote-tweet feature, blamed Dave Portnoy and Barstool’s “Trumpist Fascism” for the shooting.

“This kid died to stop a school shooter whose mother echoed the Trumpist Fascism of @stoolpresidente and @barstoolsports,” Olbermann tweets. What evidence did Olbermann have? The shooter’s mother once published a blog post in favor of Trump.

We can dismiss Olbermann as a man clearly in decline. And because of his long pattern of disturbing behavior, most have. But the sad state of Olbermann is not a singular matter. Instead, it should be a warning to the woke everywhere. Keith Olbermann is living proof of what years of lies, misery, hypocrisy, and baseless indignation do to a human. Living this way eventually takes a toll. It requires such effort to manufacture venomous hate over nothing. Plus, it never ends.

Front-facing members of the progressive movement are riding a never-ending treadmill. In Adam Carolla’s book, I’m Your Emotional Support Animal, Carolla says the continuous nature of the campaign is the very purpose of wokeness.

“Think about those two words. ‘Progressive.’ ‘Movement.’ They mean it’s never going to stop. It starts by moving toward real problems, but when the people in the movement run out of real problems, they still need to keep progressing, keep moving, and that’s where we’re at now.”

In essence, progressive fighters never reach gratification. (Take that however you will.) So they start in a dark place and never escape. They are loyal social media foot soldiers who sacrifice their own personal lives for the sake of the cause.

What’s most troubling about this dynamic is that other Twitter users have been misled about its root cause. There’s a misconception that career race-baiters have brainwashed their followers. That’s not entirely true. Instead, their followers have actually convinced them that they must continually uncover racism, even where none exists. Meaning, they must plumb the depths that have no bottom.

Their followers and algorithms now encourage them to address whole demographics rather than focus on a few individuals. That’s why Jemele Hill, a very gross individual, now focuses on white women as a species, rather than Kelly Loeffler and Marjorie Taylor Greene individually as she once did. Olbermann knows that direction well.

Progressive tweeters with large followings are motivated by the approval they get from retweets, likes, and follows on social media. And a recent Pew study found that 10% of Twitter users make up 92% of the platform’s engagement. So who is this 10%? Ideologically, they amass a political leaning of D+43. In other words, it’s a class of radicals, most of whom likely prefer modern segregation to freedom.

The audience that progressives aim to please has created an atmosphere that demands daily evidence of systemic racism, transphobia, “Trump Fascism,” and anti-vax misinformation. Think of the drain this must take on the movement’s public faces. They are trying to constantly appease the unappeasable. 

Ultimately, the woke become a caricature of their own ideology because no one can be that offended, bothered, and imaginative all the time. And playing a character is a dangerous game. After so long, you become what you portray.

That’s why these people struggle to transition themselves out of their poisonous mindset and enjoy their lives. It’s almost impossible to do. Thus, it’s no coincidence that Olbermann, 62, is not married. Who would want to live with a guy like that, day after day? Sadly, the data shows that he may not be alone in being alone. About 10% of Americans claim to have zero friends in their life. How many such Americans consider themselves “woke”?

Race-hustling is a lonely life and the sacrifice hardly pays off.

No matter how well you’ve saved your inherited get-out-of-jail-free cards — which include your name, picture, and preferred pronouns — the same faction that you helped grow will turn on you the moment it’s advantageous to do so. Because the demand for white nationalism far exceeds the supply, those on the hunt will eventually run out of external targets and turn on their own.

“It doesn’t matter how many chips you deposit in the Woke Bank,” Megyn Kelly, one of the few hosts with any individuality, told me. “They will come for you, they will cut you.”

Let Christy Teegan serve as an example. Or former BLM amplifier Rachel Nichols, whom fellow BLM supporters labeled a racist as they sent her away from ESPN jobless and scarred for life. Chris Cuomo re-labeled his primetime program the “COVID command center.” Now, his former supporters in the press are calling for the death of his career. Despite Olbermann’s work toward the cause for over two decades, not a single MSNBC or CNN host will invite him on their programs today. His group members are watching and letting him deteriorate.

Perhaps progressives will tear down the country and ensure their own ominous ending. In fact, they probably will, if others, who vastly outnumber them, don’t start fighting back. But either way, almost none of those currently working to ravage the country will make it out unscathed and in a healthy mental state.

Again, this is not a theory. There’s detailed proof of how this ends.

Keith Olbermann was once the gold standard of two media industries: sports and news. God, whom Olbermann loathes, gifted him with superb delivery and skill. Olbermann went from cheering with Dan Patrick on SportsCenter to preaching on MSNBC with the industry’s top staff. Now, he’s left screaming into an iPhone on his balcony with no human interaction in sight:


And it’s coming for all of them: Ibram X. Kendi, Joy Reid, Don Lemon, Ilhan Omar, birthing persons, Nikole Hannah-Jones, and those in their lonely Upper East Side apartments. 

The sad state of Keith Olbermann is how life ends for the woke.

Written by Bobby Burack

Bobby Burack is a writer for OutKick where he reports and analyzes the latest topics in media, culture, sports, and politics..

Burack has become a prominent voice in media and has been featured on several shows across OutKick and industry related podcasts and radio stations.


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  1. The first thing we need to cease doing is referring to leftists as “progressive.” There is nothing progressive about their ideology. It is rooted in regression, the destruction of the idea of the individual, and the dissolution of any “right” they see as not conforming with their social structure.

  2. “Keith Olbermann was once the gold standard of two media industries: sports and news.”

    Stop. This isn’t about left vs. right or wokeism. Bathtub Boy is a first class Grade A fucking asshole. Decades worth of complaints about his behavior, getting fired from every job he’s had (or fired without being fired, ask a former Yankees manager named Joe how that works), insane rants that started long before Orange Man came onto the scene, egotistical behavior, mysoginistic attitude, it was all there. People like Burack, Whitlock and Travis want to pretend he went off the deep end because of Trump because they’d have to admit a friend/inspiration/hero wasn’t a piece of shit from the get-go.

    He’s fucking garbage and he always was garbage. Justifying it with “he was cool on Sportscenter once” isn’t going to change that.

  3. FWIW … the only place I ever see Olbermann’s name or his latest insane rant is here on Outkick. ,,,

    Now I don’t do Twitter but I am active on Facebook with 5,000 like-minded “followers” who share left-wing media terrorists’ rants very closely … but never anything from Olbermann or Jamele Hill. I’m not suggesting Outkick NOT report KO’s insanity but know that you give him far more “publicity” than he might warrant. I firmly believe in the 10% Rule.

  4. Keith Olbermann is living proof of what years of lies, misery, hypocrisy, and baseless indignation do to a human. Living this way eventually takes a toll. It requires such effort to manufacture venomous hate over nothing. And it never ends.

    Sadly true. Orwell said it first.

  5. Great article Bobby. Olberman is a good example of the great unwinding that is about to occur.

    The ubiquitous sympathy for black criminals generated by the George Fentanyl Floyd* video pushed these Woketards into a powerful position…. but then bLM, antifa and the Joy Reids of the world showed everyone else their CRT / black and criminal supremacy agenda … now the nation is gearing up to turn on them, hard and fast… it’s gonna get ugly for the Woke…

    *(may His Reverend High Holiness rest in peace in his golden casket as we all kneel in our kinte cloths with Nancy Pelosi and Chuck Schumer before His statue)

    TRUTH BOMB: “Because the demand for white nationalism far exceeds the supply…” they have to manufacture it. Jussie Smollett, Bubba “noose boy” Wallace, Covington Catholic / Nick Sandmann, etc. etc.

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