Is Keith Olbermann Playing A Character Or Actually Evil And Deranged?

Keith Olbermann is either punking us or crying for help.

Admittedly, OutKick has mostly treated Keith Olbermann as a joke. He is the only two-time winner of our annual Woke All-Star Challenge for a reason. We’ve also taken sport in highlighting his bombastic attacks on OutKick personalities, including Clay Travis, Tomi Lahren, Riley Gaines, and me.

Olbermann has descended into a caricature of the bitter, deranged leftist. He’s an aging man shouting into the void through his selfie stick. What has never been clear, however, is how much of the act is real. His former ESPN colleagues will tell you he has always been eccentric, volatile, and emotionally erratic, yet nothing resembling what he has become.

For years, I viewed Olbermann through the lens of professional wrestling, like a heel manager playing an exaggerated version of his real self. And as an almost 70-year-old, unmarried, childless man with tens of millions presumably in the bank, he has little to lose.

Yet it struck me recently that maybe we are the ignorant ones. Perhaps we’ve dismissed Olbermann’s rants as performance when they are, in fact, warning signs.

Olbermann Threatens Scott Jennings

On Monday night, Olbermann appeared to threaten CNN conservative commentator Scott Jennings. "You’re next, motherf--ker," he wrote on social media.

Jennings took the remark as a threat of violence and tagged the FBI. Olbermann backtracked, claiming he meant Jennings’ career was "next" to be canceled, not his life. He added that Jennings should "send a tape to Real America’s Voice" and ridiculed him as an "amateur."

This was not an isolated moment of poor judgment. It follows a disturbing pattern since the death of Charlie Kirk. Last week, Olbermann posted a video seemingly rationalizing the assassination, defending the alleged killer’s motives. "It was simply a man protecting someone he loved," he said of Tyler Robinson and his trans partner.

Days later, he told the Sinclair Broadcasting company to "burn in hell alongside Charlie Kirk."

Even more troubling, his physical state now mirrors his rhetoric. In recent videos, he appears pale, gaunt, and frail. At times, he sits with his arms folded tightly, resembling someone still restrained by a straitjacket.

Maybe the best indication that Olbermann is mentally deteriorating is the fact that he never needed to be this desperate. 

Keith Olbermann is one of the most gifted broadcasters of the past 30 years. His cadence, delivery, and novel-like monologues are not replicable. In fact, many of us who now mock him once admired him. He blazed the trail for commentators who seamlessly merged sports and politics.

Will Cain acknowledged as much when he left ESPN for Fox News in 2020, noting that Olbermann helped make such a career path possible.

To my 12-year-old self, the idea that Olbermann would one day read my work and tweet at me would have been exhilarating. Now, when he smears me as a "lying MAGA disease-addled child," it’s disheartening.

Warning to the Woke

Three years ago, we explained how other deranged leftists should view the sad state of Keith Olbermann as a warning: this is how it ends.

The symptoms of "Olbermann-ism," if you will, are evident in others: Ilhan Omar, Rashida Tlaib, Jasmine Crockett, and Stephen King, to name a few. They each embody what years of grievance, resentment, and ideological fanaticism can do to a person. Living in perpetual outrage is unsustainable. 

Manufacturing venomous hate over trivialities eventually breaks a person. Just look at Olbermann. 

As Matt Walsh put it last week, Olbermann is living in Hell. "Old, unemployed, irrelevant, fired from every job he ever had, unmarried and childless, spending his final years alone, shitposting into the void, begging to be noticed."  

Walsh concluded that when Olbermann dies, there will be no legacy and no one to mourn him. Cruel? Maybe. Accurate? Almost certainly.

Ultimately, whether he’s acting, clinically insane, or possessed by demons, Keith Olbermann is not well. It doesn’t appear he’s taking care of himself. He can be found posting online as early as 4 a.m. and as late as 3 a.m. That is not the rhythm of a healthy man with friends, structure, or purpose.

His rhetoric is increasingly indistinguishable from that of Antifa and other violent extremists. He resembles someone Americans should be cautious around, someone they’d avoid on a subway or in a park.

We should no longer dismiss Keith Olbermann as just some goofy, harmless radical. A man who spews such vivid hatred in today's political climate ought not to be taken lightly.

Maybe the authorities should visit Olbermann, as Jennings suggests. Just to check on him.