On September 7, 2025, the city of Chicago found itself at the heart of a national firestorm, as President Donald Trump’s threats to deploy federal troops and potentially occupy the city sparked outrage, fear, and a surge of grassroots organizing. The controversy ignited after Trump posted an AI-generated war poster on social media, depicting himself as Lieutenant Colonel Bill Kilgore from the film Apocalypse Now. In the image, helicopters hovered over a burning Chicago skyline, with the chilling phrase, “I love the smell of deportations in the morning.” Other provocative captions included, “Chicago about to find out why it’s called the Department of WAR,” and “ChipocalypseNow,” all layered with helicopter emojis and a sense of looming menace.
According to reporting by Ken Klippenstein, the White House had made formal requests for military “support infrastructure,” including highway access, fuel, and other logistical nodes, with the Great Lakes Naval Station in North Chicago identified as a staging ground—just 30 miles from downtown. The prospect of federal troops moving into Chicago, and possibly other cities like New Orleans, sent shockwaves through the city’s political and civic landscape.
For many Chicagoans, the AI-generated image was more than internet bravado; it was psychological warfare. As Organizing My Thoughts described, “Trump’s theatrics of annihilation are disorienting, racist, and enraging.” The post blurred the boundaries between fantasy and policy, raising real fears for residents—especially immigrants and communities of color—who have long been targeted by aggressive federal enforcement. “He wants us to see his violence as inevitable and inescapable. He wins when we recoil and retreat from one another—a job that was half done from the start in this alienated, fractured society,” the newsletter observed.
Yet, instead of succumbing to panic, Chicago’s civic institutions and grassroots organizations sprang into action. On the same day the AI poster went viral, the Chicago Teachers Union (CTU) convened an all-member tele-town hall at 7 p.m. to strategize ways to protect students and families should federal troops arrive. The CTU’s message was clear: “Solidarity is our strength. And there is power in our union.” The union’s leadership, including President Stacy Davis Gates, emphasized the need for collective action, distributing “Defend Your Rights” flyers at schools across the city and launching a weekly “Sidewalk Solidarity” campaign to ensure parents and students know their rights in the event of a federal occupation.
On Labor Day, September 5, thousands of Chicagoans marched through the city in one of the largest rallies in recent memory, sending a resounding message to Washington. Mayor Brandon Johnson, CTU President Stacy Davis Gates, and other city leaders stood shoulder to shoulder, denouncing Trump’s threats and vowing to defend Chicago’s democracy. “Solidarity is how you defeat fascism,” Davis Gates told the crowd, her words echoing through a sea of union banners and handmade signs. “Solidarity is how you defeat white supremacy. It is how you defeat racism.”
The sense of unity extended far beyond the rally. At Nash Elementary, Davis Gates was joined by Mayor Johnson, Chicago Public Schools CEO Macquline King, and other education leaders in a powerful show of support for students and families. The CTU’s efforts were amplified by local volunteers who monitored the Mexican Independence Day Parade in Pilsen for ICE activity, demonstrating the city’s commitment to protecting its most vulnerable residents.
Chicago’s response wasn’t just reactive—it was deeply rooted in the city’s identity as a sanctuary for immigrants and a bastion of organized labor. As the CTU stated unequivocally, “Safety does not come from federal forces invading our city. Real safety comes from the types of community investments that Mayor Brandon Johnson has made into public health, public education, summer youth jobs, affordable housing, small business development and mental health care.”
Legal developments added another layer of complexity. A recent court ruling declared Trump’s deployment of federal troops to Los Angeles illegal, casting doubt on the legality of any similar action in Chicago. U.S. District Judge Charles Breyer wrote, “Donald Trump appears fixated on ‘creating a national police force with the President as its chief,’” and held that such deployments to enforce immigration laws were beyond the president’s authority. This legal setback may have complicated White House plans, but uncertainty remained about how far the administration might go.
Trump’s rhetoric and tactics have drawn sharp rebukes from across the political spectrum. Chicago’s mayor, Brandon Johnson, and Illinois Governor J.B. Pritzker have both publicly opposed the idea of federal occupation, standing firm against what they see as a dangerous precedent. Community leaders and activists, meanwhile, have doubled down on organizing—mapping local resources, holding workshops, and preparing coordinated responses to protect their neighbors. As one organizer put it, “While Trump sought to panic and demoralize us, we instead sharpened our thinking and doubled down on our commitments to each other.”
The threat of occupation has also galvanized educators, who see their role as defenders of both students and democracy. The CTU’s upcoming Annual Lead Dinner, scheduled for September 19 with keynote speaker Nina Turner, will celebrate the union’s fight for equity and justice in the face of federal intimidation. “It’s more important than ever that we stand united as educators, elected officials, faith leaders and community advocates to say NO Trump takeover and YES to the resources our communities actually need,” the CTU declared in its announcement.
Chicago’s resistance is part of a broader national movement. Labor Day saw over 1,000 demonstrations across the United States, as unions, faith groups, and community organizations rallied against what many view as an assault on civil liberties and local autonomy. The city’s stance has drawn national attention, with CTU President Davis Gates appearing on CNN and MSNBC to articulate the stakes: “We reject occupation,” she said plainly, “and we will not back down.”
As Chicago braces for whatever comes next, its people are refusing to be defined by fear. Instead, they are reaching for each other, building networks of care and protection, and reaffirming their commitment to justice and solidarity. The city’s message to the White House is unmistakable: Chicago is a union town, and its residents will not be conquered. They will stand together—loud, proud, and unbowed—no matter what challenges lie ahead.
