Trump wants a war with blue cities And Chicago might give him one

In 2016, I was in the media pen in a downtown Chicago arena during a particularly infamous Donald Trump rally. The crowd — an uneasy mix of MAGA types with anti-Trump students and activists — simmered with tension. Then word spread: Trump had bailed because he worried about potential violence. Cheers erupted. Protesters waved banners and chanted lyrics to the Kendrick Lamar song “Alright” as angry Trump supporters filed out. Some minor scuffles spilled out into the cold March streets, but the mood was largely triumphant; it appeared as if the City of Broad Shoulders was the only city with the swagger to stand up to him. Marco Rubio, then the future president’s primary opponent, compared Trump to a “third-world strongman.” Nearly a decade later, President Trump is enacting his revenge against Chicago in a manner that surely makes Rubio’s statement look like prophecy.

Welcome to what might as well be called Trump’s “Deep Blue City Revenge Tour,” which has seen him using the power of the presidency — and then some — to confront liberal urban strongholds. In recent months, he’s dispatched the National Guard to Los Angeles and Washington, DC, and this week also authorized roughly 500 troops to Chicago, despite objections from state and local leaders. In a recent speech, he said he told Secretary of War Pete Hegseth, “We should use some of these dangerous cities as training grounds for our military.” He acknowledged critics who say he’s gone too far in using federal troops domestically, but brushed them off: “America is under invasion from within. No different than a foreign enemy, but more difficult because they don’t wear uniforms.”

This language — war metaphors, occupation logic — signals something larger than bog-standard conservative law-and-order politics. Since the assassination of Charlie Kirk, Trump has sharpened a moral vocabulary that fuses the populist Right’s fear of urban chaos with the militarism of a besieged empire, and declared a war against the “radical Left” in cities that once humiliated or opposed him. 

Saving a city from invasion by invading it with out-of-state troops is a hell of a contradiction, but Trump’s game might be intentional bear-baiting. Indeed, as the National Guard enters Chicago this week, the city is caught in a perverse optics game. If it fights back too hard against the occupying troops, it becomes the poster child for instability. If it bows or accedes quietly, it concedes the logic of militarized control. Either path validates Trump’s claim that blue cities must suppress themselves or be suppressed.

Ironically, Chicago isn’t actually seething with unrest at the moment. Like much of urban America, it is quieter now than it was a few years ago — no George Floyd-era protests in the streets, no sky-high homicide spikes like those of 2022 or 2023. There are small pockets of resistance against ICE deportations and scattered Boomer-heavy “No Kings” protests, but the agitation remains marginal. The supposed “war zones” are mostly calm, or at least for now. 

But in Chicago, the instinct towards confrontation — for both better or worse — runs deep. Consider that for nearly its entire two-century existence, the city has been a stage for resistance and repression, from the 1886 bombing at a labor rally in Haymarket Square during a protest for the 8-hour workday, to the Pullman Strike, the largest-ever organized work stoppage in 1894. During the 1968 Democratic National Convention, the “whole world was watching” as thousands of Yippies and other anti-war protestors clashed with police; and more recently, Chicago roiled with widespread demonstrations, riots, and arson during the summer of 2020. Chicago may ultimately serve as Trump’s perfect trap because the city can’t not resist. But in doing so, it risks giving Trump exactly what he wants: the imagery of chaos, the spectacle of unrest, the “war from within” that justifies extraordinary measures. 

One undersung event that offers haunting parallel to the present is the fierce labor battle of 1877. That summer, railway workers went on strike in dramatic fashion, and President Rutherford B. Hayes invoked the Insurrection Act that Trump is reportedly also considering utilizing. Hayes sent federal troops to crush the uprising and reopen the rail lines, mobilizing some 45,000 militiamen from 15 states. As historian Eleanor Hannah noted, the presence of the National Guard may have exacerbated the situation in Chicago. “…They turned previously nonviolent crowds into frightening mobs. Urban crowds could outnumber the Guard companies by the hundreds and even the thousands. These crowds presented special challenges because the only real training guardsmen had for dealing with large, hostile forces was military — despite the name riot duty.”

The escalation ended in tragedy with the “Battle of the Viaduct,” fought two blocks from my old South Side apartment on Halsted Street. Guardsmen and federal troops who’d been fighting the Sioux turned their muskets and artillery guns on thousands of striking workers and sympathizers, mostly Irish and Czech immigrants, many of them under the age of 18, who wielded stones and clubs. The Chicago Police and troops suffered no fatalities and 18 injuries during the three-day uprising, while the protesters suffered roughly 20 dead and 200 injured. The city’s elite and industrialists responded by formalizing the Illinois National Guard and financing Fort Sheridan, an army base built specifically to deploy troops against labor. They even donated cannons and a Gatling gun to the city for the cause. 

That bloody history has never entirely faded. When Trump deploys troops today, under the same Illinois National Guard banner established in 1877, he is echoing ancient Chicago lore but with profound irony. The 19th-century industrialists wanted to suppress a genuine uprising. Trump, in contrast, appears to want to manufacture one using the same Illinois National Guard that once killed immigrant strikers.

To be fair, this week’s deployment is a modest force compared to the 19th century or, for instance, the tens, if not hundreds, of thousands deployed in Iraq or Afghanistan. Still, it’s large enough to stage a show sufficient to create the kind of street-level confrontations that can metastasize into national spectacles and justify a further crackdown. The rise of recent lone-wolf violence — shootings, stabbings, random attacks — also gives Trump the rhetorical pretext he needs. He can frame each new violent act as a thread in a tapestry of urban collapse, to be contained only via the military, even in domestic neighborhoods.  

There are signs of resistance already. On Oct. 4, in Chicago’s Brighton Park neighborhood, Border Patrol agents shot a 30-year-old woman, Marimar Martinez, amid protests targeting increased ICE activity after she was involved in an alleged vehicle chase that ended in her ramming a CBP vehicle. Illinois Gov. J.B. Pritzker has sued to block the deployment, calling it part of an “authoritarian march.” Mayor Brandon Johnson signed an executive order barring ICE from operating on city-owned property and has publicly denounced Trump’s threats. When Trump posted that Pritzker and Johnson “should be in jail,” accusing them of failing to protect federal agents, both responded defiantly. Pritzker on X: “Trump is now calling for the arrest of elected representatives checking his power. What else is left on the path to full-blown authoritarianism?” Johnson replied, “I’m not going anywhere.”

Or is he? If the city meets force with force, Trump likely wins. If it retreats into anxious silence, he also wins. The challenge for Chicago, and for America’s liberal cities more broadly, is to find a language of defiance that denies him the spectacle he craves. The lesson of the city’s storied history isn’t that resistance is futile — it’s that resistance, without a strategy and strong allies, becomes fuel for repression. Trump is counting on that.

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