How I Learned to Spot an Autocrat

Authoritarians like Trump follow a familiar pattern. Trygve Olson has an eight-part guide on how they operate — and how they can be defeated.

By Trygve Olson

This is the introduction to an eight-part series on the lessons I've learned confronting autocrats over the past thirty years. From post-Soviet capitals, across Africa, Asia, and South America to the frontline in America Today, I’ve seen how authoritarianism grows — and how democracy survives.

I didn’t grow up thinking I’d become an expert on authoritarian regimes. I was a kid from River Falls, Wisconsin (my favorite place in the entire world to this day) — population under 10,000. My early years were spent in church basements, hockey rinks, and on the banks of the Kinnickinnic River. I memorized electoral maps instead of baseball cards. My first political campaign was dropping literature in third grade.

But life has a way of handing you assignments you didn’t apply for.

In 2001, I found myself on the ninth floor of the Planeta Hotel in Minsk, Belarus, being watched by two of the scariest men I’d ever seen. They weren’t hiding it. I was there working for the International Republican Institute (IRI) lead by Senator John McCain, helping pro-democracy activists challenge Alexander Lukashenko. The same Lukashenko who used to shut down city streets to rollerblade alone and had opposition leaders disappear.

That trip showed me what authoritarianism looks like up close. It’s not subtle. It’s not theoretical. It’s fear you can feel in your spine. It’s people whispering in safe apartments because their phones are bugged. It’s political leaders who can’t answer simple questions because they’re terrified of saying the wrong thing and being put in jail or simply never being seen again.

And once you’ve seen it, you know what to look for. Which is why when Donald Trump descended that escalator in 2015, I didn’t see a joke. I saw a danger. The language. The need for loyalty. The war on facts. The obsession with enemies. The performative toughness. It felt familiar. Too familiar.

Authoritarians all follow a playbook. Some are more competent than others. Some dress it up in religion or nationalism. Some don’t even bother. But the core is always the same: zero-sum power, manufactured grievance, and the destruction of democratic norms.

That’s why I started speaking out.

Not as a Democrat. I’m not one. Not as someone who thinks America is Belarus. It isn’t.

But as someone who has spent twenty years helping people in Belarus, Serbia, Georgia, Ukraine, and far beyond fight men with Autocratic Personality Disorder (a term I coined long ago). And as someone who saw too many good Americans, including many back home in Wisconsin fall for the same con.

This series is about what I’ve learned. The personalities. The tactics. The lessons. And what it means for us now as Americans who are standing up to meet the challenge.

Because democracy is not self-cleaning. And once you’ve seen the basement, you recognize when the upstairs is starting to rot.

Trygve Olson is a strategist, pro-democracy fighter and a founding Lincoln Project advisor. He writes the Searching for Hope Substack. Read the original column here.

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