Trump wants to make war on Chicago. He picked the wrong fight.

Donald Trump is starting to remind me of Madonna as her triumphant 1980s morphed into the 1990s, and she had to get crazier and crazier to still get people’s attention — finally releasing a pornographic “coffee table” (heh) book called simply, Sex.

The president’s version of Sex came Saturday in the form of a Truth Social post in which he theatrically promised to launch a fiery war against America’s third-largest city — 2.721 million U.S. citizens he’d sworn on a Bible to defend, not attack.

Trump’s “Chipocalypse Now” meme might sound like the newest Ben and Jerry’s flavor, but actually invoked the dark 1979 Vietnam War drama Apocalypse Now, with an image of POTUS 47 in a 1969-era U.S. Cavalry hat mimicking the Army colonel played by Robert Duvall in the classic film.

“I love the smell of deportation in the morning,” Trump posted, echoing Duvall’s famous line, “I love the smell of napalm in the morning.” The post, styled in movie poster imagery, shows a fleet of military helicopters backdropped by the Chicago skyline, with ominous flames behind the faux-officer Trump. Then, a reference to Trump’s attempted name change at the Pentagon: “Chicago about to find out why it’s called the Department of WAR,” punctuated by three helicopter icons.

It’s way too easy to point out the ironies here — that in the actual late 1960s, a cowardly Trump was claiming bone spurs on his feet as an excuse not to fight in Vietnam, or that Apocalypse Now was a deep dive into the utter insanity of war, not a celebration of military might. But the president of the United States making a martial threat against a large city led by the opposition political party must be taken both literally and seriously.

Stepped-up federal immigration raids and arrests are clearly imminent in the Windy City, as the Trump regime has dispatched some 300 additional agents from U.S. Immigration and Customs Enforcement, or ICE, to a secure staging area at the Naval Station Great Lakes, a military base on the outskirts of the city. There have been constant threats to support this operation with federalized National Guard troops or even active-duty soldiers, in an echo of recent operations in Los Angeles and Washington.

The implications of Trump’s Saturday morning threat against Chicago are almost beyond belief: That a city that was once the epitome of American economic hustle and might at the peak of the Industrial Revolution is now considered hostile territory by the U.S. government, dehumanizing its citizens as the enemy.

I couldn’t help but think back to 2001, when an ultraconservative Republican president from Texas — George W. Bush — was in the White House. Bush had received barely 18% of the 2000 presidential vote in liberal-leaning New York, but that didn’t stop him from racing to Lower Manhattan with a bullhorn after the Sept. 11, 2001, terror attacks, vowing to rebuild the city. Just a generation later, today’s GOP president is threatening a fiery inferno against a city that voted against him. This is how far, and how fast, America has fallen.

It’s important to see the “Chipocalypse Now” meme as part of a much bigger picture. In the reality-based world, Trump is struggling. His poll numbers are way down, scores of judges — including GOP appointees — are striking down his policy initiatives, a resurfaced Jeffrey Epstein scandal is nipping at his heels, and there are serious questions about his health and his vigor to do the job.

Trump’s reaction has been to double down on strongman posturing — some of it sheer bluster, some of it with deadly, or potentially deadly, real-world consequences. In the latter category sits Trump’s order for U.S. troops to blow up a boat in the Caribbean and kill all 11 onboard civilians — on unsubstantiated allegations of drug trafficking — amid signs the regime is eager to foment a war with Venezuela. In the bluster department comes the president’s wasteful and ahistorical scheme to rename the U.S. Department of Defense as the Department of War — and instantly then threaten to deploy against U.S. citizens.

The White House’s Chicago maneuvers are right on the fulcrum between hype and reality, and what plays out in the flat, sprawling metropolis over the coming days and weeks is likely to determine just how far Trump can take his experiment in American dictatorship.

» READ MORE: Trump won’t get to heaven if he keeps murdering people on boats | Will Bunch

We’ve seen our biggest institutions — Congress, the U.S. Supreme Court, university presidents, white-shoe law firms, and Big Media — cower and kowtow to a man who would be king, but Illinois’ top Democrats have so far given a master class in what high-level resistance is supposed to look like.

That’s especially true of Illinois Gov. JB Pritzker, who has not only denounced the Trump regime’s plans for Chicago in the strongest possible terms — “Illinois won’t be intimidated by a wannabe dictator,” he posted Saturday in a response to the “Chipocalypse Now” meme — but also borrowed a tactic Joe Biden deployed ahead of Russia’s invasion of Ukraine. Pritzker revealed his advance intelligence on the government’s plans — possible ICE raids at Mexican Independence Day parades, or deploying troops from the Texas National Guard — in the hope that negative publicity would prevent those things from happening.

Pritzker’s boldness has been reinforced by Chicago’s progressive mayor, Brandon Johnson — who issued an executive order that federal agents within the city must wear badges but not masks, and deploy body cameras, while largely barring his own cops from cooperating with ICE — and Democratic U.S. Sen. Tammy Duckworth, who raised a clenched fist at a Chicago protest against the ICE presence.

But some of this is clearly symbolic. Chicago cops don’t really have the legal authority to stop and arrest ICE’s masked goon squads. While it’s fascinating to imagine the prospect of Pritzker dispatching an endless convoy of Illinois state troopers — ripped from the climax of The Blues Brothers — to Cairo, Ill., to blockade the Texas National Guard, it’s unlikely we’ll see the first battle of Civil War II. At least not yet.

Even Pritzker has acknowledged that the best hope of thwarting Trump’s Chicago schemes won’t come from urban warfare, but from the federal courts. There, it’s not hard to imagine that even a Republican-appointed judge might strike down either the federalizing of troops without any emergency — with crime, the supposed pretext, falling dramatically in Chicago — or the wildly unconstitutional notion of guard members invading from another state such as Texas. Yet, the regime has also shown an ability to delay or even defy court orders in its first eight months, making it unclear if the judiciary can truly save Chicago.

But what Pritzker and his allies have actually accomplished is something arguably more powerful. They have sent the message to everyday Chicago residents that acquiescence to authoritarianism is not an option, and that someone will have their back if and when they resist.

Just hours after Trump’s warlike threat, incredible scenes took place across Chicago. Thousands of Latinos and their allies turned out for Mexican Independence Day parades, and ICE — thanks, perhaps, to Pritzker’s advance warning — did not show up to disrupt the day. With the September sun setting behind the city’s towering skyscrapers, thousands more came downtown for a massive protest march against ICE’s presence.

Walking in the storied footsteps of 19th-century labor radicals, the Rev. Dr. Martin Luther King Jr.’s civil rights crusade, and 1968’s anti-war protesters, thousands of marchers overflowed the city’s “Magnificent Mile” on Michigan Avenue, carrying signs like, “ICE Out of Chicago,” and chanting, “We ain’t free till we all free.” And they were not alone. Hours earlier, a similarly large and boisterous march approached the White House, protesting the troop presence in D.C.

Can nonviolent popular resistance against Trump really work? Arguably, it already has.

In Los Angeles, National Guard troops and Marines called out this spring have gone home, and a period of stepped-up ICE raids appears to be largely over, with some of the excess federal agents there apparently moved to Chicago. What happened in Southern California — opposition from Democratic Gov. Gavin Newsom and others, which led to court orders that sharply curtailed federal operations, as well as citizen protests — should be a template for Chicago to resist.

Indeed, earlier last week, in the wake of Pritzker’s initial strong statement of noncompliance, Trump did something he rarely ever does. He seemed to back down slightly, suggesting he might instead send troops to New Orleans, in a state with a solidly MAGA Republican governor. The moment was a reminder that dictatorship is not destiny.

In seeking to cement his American autocracy, Trump has strived to emulate both the worst dictators of the 20th century as well as their modern variants, like Hungarian strongman Viktor Orbán, and echoed their success in crushing once-proud institutions. Where Trump’s U.S. project falters is in the strong will of the people.

Despite our well-documented flaws, a passion for democracy still burns brightly for millions of Americans that can’t easily be extinguished. Nowhere is that more true than in a city of light called Chicago. If Trump’s “Department of War” is serious about staging its first battle on the shores of Lake Michigan, it picked the wrong fight.

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