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Inside Trump’s Plot To Terrorize Chicago

Sources in the administration tell Zeteo that Trump is also seriously discussing invoking the Insurrection Act with his top advisers.

Asawin Suebsaeng's avatar
Asawin Suebsaeng
Oct 10, 2025
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Federal agents watch as demonstrators protest against their presence in Chicago on Oct. 4, 2025. Photo by Joshua Lott/The Washington Post via Getty Images

It was always going to be Chicago.

The great Midwest city was destined to become the prime target of a reelected Donald Trump’s vision of turning the machinery of the so-called global ‘War on Terror’ on many millions of American civilians, domestic “enemies,” and Democrats. Trump and his lieutenants have been plotting their assault on Illinois’s liberal stronghold for much of the past decade. But in the weeks following the assassination of MAGA-aligned podcaster Charlie Kirk, the Trump White House is hoping to develop new tools for bringing the president’s new “war on terror” and loud, militarized clampdown to the streets of the Windy City, sources familiar with the situation tell Zeteo.

“Chicago Mayor should be in jail for failing to protect Ice Officers! Governor Pritzker also!” the president of the United States and nominal leader of the free world posted to social media on Wednesday morning.

Trump was barreling forth on his administration’s ambitiously authoritarian program of harassing, threatening, investigating, prosecuting, and attempting to imprison his political and cultural enemies. For some of his targets, there is no suggestion of criminal wrongdoing, beyond the crime of refusing to help Trump steal the 2020 presidential election.

And Trump’s call this week for jailing two prominent Illinois Democrats is hardly occurring in a vacuum: It’s just the latest facet of his and his party’s expansive program to crush dissent and the political opposition across the nation, and to violently terrorize liberal bastions such as Chicago for crossing the president. And it’s the culmination of years, not just months, of work.

‘We Should See Prosecutions Soar’

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