I am in St. Louis for a birthday party when I watch the video about events near my home in Chicago. My hands shake. I show the clip to a relative who I thought would understand.
“Are you safe?” she asks.
“I’m not the one they’re after,” I say.
“But still,” she tells me, “maybe don’t let Bert take the city bus. Maybe think about moving.”
“MOVE WHERE?” I want to scream. I’ve lived in Chicago for twenty-five years. I want to tell her that the point isn’t whether I am safe. The point is whether safety still exists as a public good, or whether it has been privatized, fenced off, and sold as another unattainable American dream. Some lives are protected; others are controlled. I press play again and point at the screen. “Look,” I say, “LOOK. This neighborhood is predominantly white!” I want her to understand.
She nods, uneasy. “Yeah, that’s really messed up—if the video is even real.” Then she repeats, “You should think about moving.”
That is when I realize how a siege works: It isolates outrage inside of fear. It spreads misinformation. It convinces us to retreat, because if we don’t, what will we do? Rise up and start a murderous revolution?
When I return to Chicago, I have the opportunity to speak with Anna Sobor. Anna is a mutual aid worker and a sixty-four-year-old widow who has lived in the Old Irving neighborhood since 1989. “We have been fortunate here, more or less, in our last century. But this is an autocratic regime,” she tells me over the phone as she packs for a trip to Egypt. “This is different. This is the first year in thirty-six years that I didn’t hand out candy.”
This year, her new Halloween charge is ICE watch. Anna is part of a volunteer gathering organized by Alderwoman Ruth Cruz of the 30th Ward. Anna, dressed as the Great Pumpkin, with a whistle around her neck as the new style warrants, spends Halloween at one corner of a seven-block shutdown. Trick-or-treating in Old Irving is a popular event on the northwest side. This is where my daughter and her friends like to go.
“How long has it been now?” she says, and I know what she means. The measure of time has changed. It’s been two months.
On September 8, 2025, the Department of Homeland Security announced Operation Midway Blitz, a “major enforcement surge” targeting what officials described as “criminal illegal aliens.” Within days, helicopters circled above the city, and unmarked SUVs idled outside grocery stores and Home Depot locations. By week two, hundreds of our neighbors had been kidnapped and detained. A press release dated October 4, 2025, from the Illinois Governor’s Office stated: “In the coming hours, the Trump Administration intends to federalize 300 members of the Illinois National Guard.” During an interview the same week, Governor JB Pritzker noted that Texas National Guard troops were “already federalized” and arriving in Illinois. No one could explain why troops were being deployed from Texas. Is it a coincidence that many of the migrants ICE came to detain also came up from Texas three years back when Governor Greg Abbott, along with Florida Governor Ron DeSantis, freighted migrants to sanctuary cities as a political stunt? Those buses were not the end of a story but the beginning of one. What followed is a story still unfolding about a city under siege. And we don’t use that word lightly. The word has a history here.
Norman Mailer used it in his 1968 book Miami and the Siege of Chicago to describe the police crackdown during the Democratic National Convention, an earlier collision between state power and public dissent. He described the city as a battlefield for the nation’s divided conscience. Now, fifty-seven years later, that language reads less like a metaphor and more like a blueprint: how to encircle, how to stall, how to discipline civic life. What once seemed poetic or dramatic now seems predictable and template-like, because the real-world scenario maps neatly onto his literary description.
A siege doesn’t have to involve armored vehicles or walls, though Chicago is seeing those, too. It can arrive through paperwork, rumor, and fear. It can surround us before we know we are closed in. A city can be contained by fatigue more than by force. Still, neighbors share soup and wave at children they barely know. Small gestures feel defiant. Survival becomes a ritual. A ritual becomes community. Community becomes resistance.
“Kettling” usually refers to police encircling protesters and trapping them in a ring of shields. Civil liberties groups condemn it as illegal detention. In Chicago, the kettle has expanded. The city itself has become the crowd, its boundaries policed not by riot law but by migration law. In Albany Park and Irving Park, residents filmed agents pinning people to the ground, firing pepper bullets, and threatening to use tear gas. In Lincoln Square, a WGN-TV news producer was violently detained, then released without charges. At the Broadview site, a pastor was shot in the head twice with a pepper ball. A city alderwoman who tried to intervene at a hospital in Humboldt Park was violently handled, then detained, then released. In Skokie and Evanston, unmarked cars crashed into intersections, pulling over brown-skinned drivers, detaining them, then releasing them without charges—no list of names. No footage. Just fear. Detain. Release. No Charges. The effect resembles a citywide kettle: containment by intimidation. People are afraid to walk to work, to school, to the store. Parents keep children indoors. Workers are missing shifts rather than risking checkpoints. “Enforcement zones,” they’ve been called in press releases. Residents call them traps.