Anne Applebaum: How Democracies Fail

With the world on the brink of another war, there’s no one more essential to hear from than Anne Applebaum, Pulitzer Prize-winning historian and author of Gulag, Iron Curtain, Red Famine (which cites Andrea’s grandfather, a Holodomor survivor), Twilight of Democracy, and Autocracy Inc.

In this urgent conversation, we go to the frontlines of authoritarianism, from MAGA’s playbook at home to Putin’s alliances abroad, from Orban’s Hungary to the rising threat of war with Iran.

We begin in Poland. In 2023, a broad democratic coalition ousted the far-right, anti-LGBTQ+ Law and Justice party, which had spent years eroding democratic institutions. But in a razor-thin presidential race this year, that same authoritarian force clawed its way back. The takeaway? Democracy isn’t a destination. It’s a constant, high-stakes battle.

“Everybody always wants to write the story of populism and say that it's over, or it's here for good, or we're finished, or we've won. And that's not what the story is going to look like,” says Applebaum. “This is the ongoing struggle that all of us will be in, probably for the next few decades, maybe into the foreseeable future. The argument about the nature of the state is now here with us. And neither one side nor the other has achieved a definitive victory, I would say, either in Europe or in the United States.”

Then, Iran. Trump launched airstrikes without congressional approval or public debate, risking another U.S. war. Many in the Iranian opposition welcome blows to the brutal regime, but without strategy or legality, this is more of Trump’s lawless chaos.

Meanwhile, Putin watches. His alliance with Iran is not ideological, but tactical, with one shared mission: destabilize democracies and sow chaos worldwide.

Applebaum discusses how Hungary became the MAGA model, what Poland’s resistance can teach the U.S., and why the fight for democracy is far from over.

This isn’t a time for hope alone. It’s a time to act. Because autocracy isn’t resting. And neither can we.

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