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Winners & Losers | The Comedian & the Charlatan

Stephen Colbert gets broomed off the stage for his politics, while Trump Season One villain Seb Gorka makes a comeback.

Sam Osterhout's avatar
Sam Osterhout
May 25, 2026
∙ Paid

You can’t kick a football in Washington without hitting a great candidate for Loser of the Week. Winners are somewhat harder to come by, but they exist!

This week’s Loser is one I’ve really been wanting to write about for a while, but he’s one of those Losers who’s always kind of lurking in the background, talking nonsense but never really doing much or accomplishing anything.

Now we know why: he sucks.

Let’s dig in.

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Seb Gorka, Loser

Earlier this month, the White House released its Counterterrorism Strategy. It was produced by the White House counterterrorism czar Sebastian Gorka, who is a Loser.

Is that mean-spirited? Well. Maybe. But it’s also possible that he is objectively a Loser. I shall do my best to prove it.

Let’s start with the Counterterrorism Strategy. This document is the product of a 40-year tradition, rooted in Reagan, formalized after 9/11, carried by every president of both parties — including Trump in 2018. It historically produced sober documents that named real threats and assessed real capabilities, and matched those threats and those capabilities to offer a realistic, clear-eyed strategy for mitigating the danger to Americans.

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It was, in other words, a strategy. Strategies are built around concrete steps one might take to solve a particular problem, right?

The Gorka strategy does not do that. It names a problem, yes, although it’s not the problem you think it is (more on that in a minute), but it offers no concrete solutions to the problem it names or to any problem, really. This is a culture war document, and not a very good one.

In fact, the very first thing you see here is a signed forward by Trump. He wants you to know, dear reader, that he has ended “four years of weakness, failure, surrender, and humiliation under the last administration.”

As usual, he skips a bunch of rhetorical steps. He doesn’t define weakness, failure, surrender, or humiliation, which means we sort of have to take his word for it. Were we humiliated? Who knows? His base will take his word for it and agree without evidence.

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