Responding to the Trump Administration's assault on Chicago

Don’t give a bully the fight he wants

Before we get started, mark your calendars for another upcoming City That Works event. We’ll be at Uptown Taproom on November 5th, from 5:30-7:30pm, for a conversation with Evanston Mayor and IL-09 Congressional Candidate Daniel Biss. You can RSVP here.

A federal agent aims a weapon at an individual recording them from an adjacent car near Berwyn. Source: Laura Rodriguez Presa.

For the last month, federal agencies have been working overtime to terrorize Chicagoans. Officers from Immigrations and Customers Enforcement (ICE) and Customs and Border Patrol (CBP) have been busy kicking in doors, breaking up families, and rounding up tamale vendors. They’ve also been quick to wield violence indiscriminately, tear gassing police officers and shooting clergy in the head with non-lethal rounds.¹

This is going to get worse. The President’s Deputy Chief of Staff, Stephen Miller is attacking the legitimacy of federal judges and has described the democratic party as a “domestic extremist organization.” The president has called for the arrest of our Mayor and Governor, and mused about invoking the Insurrection Act.

In the meantime, actual law enforcement activities have suffered. The Wall Street Journal reports that as a result of the Trump Administration’s actions, referrals for criminal prosecutions are falling, child exploitation cases have been put on pause, and checkpoints on key fentanyl trafficking routes are going unmanned. In Chicago, the FBI’s Joint Terrorism Task Force has been reassigned to immigration-related enforcement.

Of course public safety was never the real goal. Instead, the Trump administration is spoiling for a fight. Crime and immigration are two of the administration’s most powerful political issues. Aggressive tactics drive attention, scare vulnerable residents, and invite even more conflict.

But it’s rarely a good idea to fight a bully at the time and place of his choosing. As Georgetown Law Professor Stephen Vladeck notes, the flimsy legal rationale that the President is attempting to use to federalize the National Guard requires establishing that disorder has become so great that “the president is unable with the regular forces to execute the laws of the United States.”²

It’s insane to argue that that’s happening now, and so far, federal judges (including ones appointed by President Trump) have roundly rejected that claim. Thursday, an Illinois judge issued a temporary restraining order blocking the deployment of the National Guard on those grounds.

But pressure will continue to build and the Trump administration has promised to appeal. The Supreme Court has been notably timid in response to power grabs by the Administration. The more violence that does occur, the better the argument the Trump Administration will have in court.

What should we do right now?

Political, business and community leaders speak out against the Federal Government’s planned ‘Midway Blitz’ operation. Source: Illinois Hispanic Chamber of Commerce

I know it’s deeply unsatisfying, but in the short term, I think many of our local leaders are responding the right way. It was great to see a phalanx of politicians, community leaders, and business groups present a unified front against the Trump Administration when Operation Midway Blitz was first announced.

Governor Pritzker has been both vocal in his opposition to the Trump Administration’s flagrant abuses of power, and clear that the president is trying to create conflict to justify more troops. Importantly, CPD Superintendent Larry Snelling has also been clear that CPD will continue to enforce the law. That doesn’t and absolutely shouldn’t mean deputizing Chicago Police Officers to enforce federal immigration laws, but it does mean protecting federal agents when necessary. That’s an important part of maintaining order. It’s also an important part of making it clear to federal judges that there’s no cause to bring in the National Guard.

I wish Mayor Johnson would be a little clearer about what Chicago can and can’t do in opposition to the Trump regime, rather than simply promising ‘drastic’ action, but his comments generally strike me as responsible as well. He’s rightfully called out the Trump administration’s “war” on Chicago and looked for additional ways to block ICE’s abuses, but he isn’t encouraging residents to escalate the situation.

In the short term, we will continue to be best served by non-violent protests and resistance that builds public support and undermines the Trump administration’s lies. Researchers Omar Wasow and Rob Willer observe that:

History and research make clear that violence seen as unnecessary, whether from the state or protesters, typically reduces popular support for the political players who use it. The public’s rejection of violence they view as unjustified is consistent — so much so that it often elicits complex strategic games, with movements and the state maneuvering to portray the other as unnecessarily violent.

Sound familiar?

If you’d like to get more involved personally, I’d encourage you to get involved with your local Indivisible Chapter, and turn out for the No Kings Protest scheduled for October 18^th.

The midterms: fighting harder means fighting smarter

In the medium term though, fighting back requires retaking political power. Unfortunately, it’s not clear that Democratic leaders in Illinois, or nationally, have come to grips with what that will take.

If Democrats want to prevent Donald Trump from turning a Mitch McConnell-selected judiciary into a Steven Miller-selected one, they need to retake the Senate. In 2026, that means winning seats in places like Iowa and Texas. That’s not possible if Democratic candidates are tied down by toxically unpopular policies.

Even as polling shows that voters oppose the aggressive moves into cities, the positions that Democrats have staked out over the last few years mean that voters still trust Republicans more than Democrats on crime, immigration, and the economy.

That’s not because voters love federal agents cosplaying as RoboCop– it’s because the Biden administration staked out a toxically unpopular policy on asylum seekers that contributed to a massive spike in border crossings. The Biden Administration finally changed course in 2024, but the Democratic party is still conflicted over this issue. And some of the same lawmakers and advocacy groups who are most vocally opposing Donald Trump now, also helped lock the party into the same unpopular positions that helped him win in the first place.

The American Civil Liberties Union, for example, has been on the front lines of cases to check the Trump administration’s activities in Illinois. But the ACLU and similarly-aligned groups bitterly opposed the Biden Administration’s rollback of permissive asylum rules. I don’t fault the ACLU for being consistent – but I do fault Democratic politicians (including progressives in Illinois) for echoing demands that the party take a hardline stance on an issue that did real damage to our political chances.

We don’t have to compromise our core values. But winning in 2026 requires seeing the electorate as it is, and not as we’d like it to be. Part of that project means that Democrats and donors in Illinois need to avoid taking stances and demanding purity tests that make it impossible for Democrats in redder states to compete.

The long run: Chicago needs to get stronger

Finally, while smarter politics is a good idea, it would also help if Chicago wasn’t such an easy target. The city’s declining violence this year is a good start, but we’ll have to sustain it over time to start to shed the city’s toxic reputation on the issue. A healthier fiscal picture and growing economy would also make us a lot more resilient to the funding cuts the Trump administration is currently threatening.

And in the long run, it’s not just about playing defense. Chicago is a deep blue city in the middle of a sea of purple and red states. We should be an example of what a diverse and progressive city can accomplish – and a billboard for what better leadership can deliver. Getting there will take a lot of hard work. But there’s no time to start like the present.

1. Video here.

2. To expand on this a bit there appear to be two legal arguments at play here, nicely explained in this Brookings/Lawfare podcast. First the president’s authority to call out the Illinois National Guard relies on an interpretation of Section 10 of US Code which authorizes the President to call out the National Guard in instances of invasion or domestic insurrection (hence the need for a fight). But even if that is done, strict limits apply on the military’s rules of engagement (enshrined in the Posse Comitatus Act) prevent troops from engaging in standard law enforcement activities. In the past, the Trump Administration has tasked the Guard with activities like protecting federal property or law enforcement officers to avoid violating that requirement.

The second interpretation concerns Title 32 of US Code, which provides for a ‘hybrid mission’ that the Trump Administration will likely argue allows them to call the Texas National Guard up to Illinois. Here, the idea is that the guard is still technically under the command of Texas Governor Greg Abbott, which may allow the Trump Administration to circumvent the Posse Comitatus Act requirements. But that’s an incredible legal stretch, and functionally amounts to using the militia of one state to invade another. It’s also at odds with long-standing legal precedents on the ability of citizens of one state to be held subject the whims or requirements of citizens in another.