The Siege of Chicago

 My one-time home city of Chicago has been swarming for months now with Trump-deployed federal troops (ICE, National Guard, FBI, you name it). All of this is known only to me by hearsay—I haven't been back to the City of the Big Shoulders for years at this point—at least not for any purpose more substantial than a flight through Midway. 

But the images are inescapable for anyone following the news. ICE agents in military gear rappelling down the sides of apartment buildings; kicking down doors; searching people's homes without a warrant; ransacking people's private belongings and hauling them outside to wait in zip-ties in the backs of black vans. These are the dystopian nightmares of our news feeds. 

The images brought to mind for me Norman Mailer's old phrase: "the Siege of Chicago"—by which he christened the violent clashes between protesters and cops at Mayor Daley's Chicago-hosted 1968 Democratic Convention. Today—perhaps even more than then—Chicago is truly under siege. Did not Trump himself declare "war" on the city, when he sent in the Guard? 

I read Mailer's account of the 1968 Convention season—Miami and the Siege of Chicago—the summer before last: 2024. It seemed essential reading for the moment. The summer convention season of the 2024 campaign was already being widely compared to the 1968 presidential campaign. 

There was the same atmosphere of foreboding—the same threats of political violence (in 1968, RFK and MLK Jr. had recently been murdered; in 2024, a would-be assassin had just come within an inch of taking Trump's life at a campaign rally in Pennsylvania). Mailer writes, of that earlier summer of assassinations: "It forced one to cherish major politicians—no matter how colorless, they all had hints of charisma now that they were obviously more vulnerable to sudden death than bullfighters[.]"

People were also expecting fireworks and upheavals at the 2024 DNC similar to what had unfolded in 1968. Then, as now, an aging incumbent president had voluntarily dropped out of the race, in order to throw his backing to his Vice President (Johnson to Humphrey in '68; Biden to Harris in '24). Then, as now, that same Vice President was struggling to distance themself from the least popular aspects of their predecessor's legacy. 

Then, as now, the Democratic Party was also internally divided over a foreign war for which many of the party's Left flank blamed the incumbent president (Vietnam in 1968; Gaza in 2024). 

Oh—and of course—as if deliberately inviting the comparison—the 2024 DNC was also held in Chicago!

As it happened—though—the 2024 DNC was nowhere near as explosive as its 1968 predecessor, despite what many of us had feared. The party establishment's rapid coalescing behind Harris prevented any divisive spat from dominating the speaker's platform at the Convention. (Not that it did us any good in the end...)

But even beyond the many historical parallels between the two convention seasons—what spoke to me most about Mailer's account, reading it in 2024, was his sense of weariness and age before the prospect of looming disaster. Mailer writes that he had been preparing for a revolution all his life. If it had come just ten or fifteen years earlier, the timing would have been perfect. But in the event, it caught him on the cusp of middle age. 

Faced with the demands for upheaval at the '68 Convention—Mailer had a highly relatable sense that: "I'm getting too old for this." 

In 1968 (Mailer was then 45), he had to admit to himself that he had grown comfortable in his country. He didn't actually want it to be torn up by militancy the way he once did—as a young radical. "[H]e looked into his reluctance to lose even the America he had had, that insane warmongering technology land [....] Yet, it had allowed him to write—it had even not deprived him entirely of honors, certainly not of an income," he writes. 

In the size of his fear, he was discovering how large a loss that would be. He liked his life. He wanted it to go on, which meant that he wanted America to go on—not as it was going, not Vietnam—but what price was he really willing to pay? Was he ready to give up the pleasures of making his movies, writing his books? They were pleasures finally he did not want to lose. 

[...] And the most powerful irony for himself is that he had lived for a dozen empty hopeless years after the second world war with the bitterness, rage, and potential militancy of a real revolutionary, [...] but no revolution had arisen in the years when he was ready—the timing of his soul was apocalyptically maladroit.

 I couldn't help but feel the same way in 2024. And I feel even more that way now—over a year later. 

Back during the first Trump administration—when I was still in my twenties—I had been ready for the revolution. I was ready for whatever (nonviolent) militant demands the Resistance might make. I got myself arrested in a civil disobedience action to defend DACA. For the four years of Trump's first term, I seemed to spend every other week marching through the streets of D.C. or camped out at a vigil in Lafayette Square. 

But the Resistance didn't ultimately ask for all that much, in hindsight. Trump—while he was loathsome as always—didn't actually succeed in subverting our democracy—at least not the first time around. 

The system of our constitutional order managed—somehow—to defend itself and survive for a little bit longer. It expelled the poison that Trump represented (at least for a time). He was defeated at the polls. And even though he then promptly tried to stage a coup to reverse these results—fulfilling everyone's worst fears about him—the attempt did not work (or so we thought). 

No revolution was required. 

I therefore allowed myself (I confess) to get a bit comfortable during the Biden years—as comfortable as Mailer got in the mid-Sixties. Of course, in both our cases, we still thought we were just as much on the Left and outraged by injustice in the abstract as always. ("I am for the Revolution in principle though I haven't done much about it lately in a practical way," as Donald Barthelme once humorously told on himself.)

I left my job as a full-time activist and thought now would be a good time to go to law school. I thought: no more metaphorical fighting or civil disobedience or nonviolent militancy was needed (particularly not after we also won our campaign to pressure Biden to eliminate the vestiges of Trump's immigration policies, such as Title 42). Now that Trump's gone, my life could be about something other than resisting him, I thought. Indeed, it could be about anything. 

By the summer of 2024—however—it was clear that this supposed Thaw had been an illusion. America was not actually done with Trump. Much as I tried to convince myself otherwise, I felt on some level sure that the last-minute switcheroo on the Democratic ticket would fail, and that Trump would win the next election. 

I also knew that—the second time around—Trump would be even worse than before. He would have fewer checks on his power. The old guard of the Republican Party—the kinds of people who had headed the party's ticket in 2008 and 2012—had been thrust out of power. Their integrity had proved incompatible with the totalitarian cult of personality Trump was now building in place of the once-Grand Old Party. 

Which meant that—if Trump did win—then I'd have to jump into the Resistance again. I'd have to go revolutionary once more—the revolutionary I would have happily been if the Revolution had come during Trump's first term; but which I found myself now too psychologically exhausted to prepare for. 

The revolution had come at last—but, just as it had for Mailer—it had come "rather late for me," to borrow a phrase from Philip Larkin. It was just a couple years behind schedule. The "timing of [my] soul," as Mailer puts it, "was apocalyptically maladroit."

And so now, here we are, in 2025. And Trump is actually doing the whole authoritarian takeover bag. He's doing it for real this time—with no comfortable guardrails of normal America still refereeing from the sidelines and making sure he doesn't get too out of hand. 

The putsch we all feared in Trump's first term—and that never succeeded—is back now, just a few years later—and it's catching us at the worst moment. It's catching us when we were basking from the glow of an earlier victory—when we thought we were done with all this, and could safely retire. 

Someone who has never known comfort or reassurance can be goaded into the sacrifices that a long revolutionary struggle demands. Someone who has been rudely plucked from the cocoon of reassurance, however—someone who thought the struggle was over—Beowulf enjoying a cozy old age and dining out on his former adventures—well... that is a person who is generally not up to the challenge. 

And so I see the young people wearing inflatable frog costumes and chicken costumes camped outside of ICE detention facilities in Chicago and Portland. I see people I went to divinity school with a decade ago getting pepper-sprayed or arrested or manhandled by federal agents—and I think: how do they have the energy and stamina for this? How are they game to resist another Siege of Chicago? I applaud them for it. I salute them for it. But I can scarcely understand it. 

But perhaps that's just because I'm reading and writing about all this on a computer screen. If I were there, in the besieged city itself, the force of events might just carry me along in spite of myself. Indeed—before every "No Kings" protest this year in Providence—I've felt the same malaise; the same exhaustion. "I'm not up for this anymore," I would say. But then I'd go—I'd do it—and the energy would come. 

Mailer too, after all—even in comfortable middle age—still went out there, onto the streets. He still joined the protesting multitude. And his record of the Siege remains the best and fullest we have.