Coffee Break: Trump’s Imperial Boomerang Gets Different Reactions in Chicago, D.C.

As Donald Trump threatens to hit Chicago with the imperial boomerang, Chicago Mayor Brandon Johnson fights back with an executive order that contrasts sharply with the reaction of Washington, D.C. Mayor Muriel Bowser.

Let’s start with a Trump meme and Illinois Democratic Senator Tammy Duckworth’s response:

Take off that Cavalry hat, you draft dodger.

You didn’t earn the right to wear it.

Stolen valor at its worst. pic.twitter.com/tJ1KdA6lU6

— Tammy Duckworth (@SenDuckworth) September 6, 2025

Duckworth’s focus on Trump’s hat in the AI generated meme drew criticism from Ken Klippenstein among others for completely missing the point. Klippenstein said, “This is everything that’s wrong with the opposition party. They obsess over rules while completely missing the main point, in this case a federal invasion of a major American city.”

After having covered Gavin Newsom’s legalist response to Trump’s militarization of Los Angeles, Chicago Mayor Brandon Johnson’s executive order to resist the federal incursion was a new twist.

Here’s what Johnson told CNN:

“We may see militarized immigration enforcement. We may also see National Guard troops. We may even see active duty military and armed vehicles in our streets. We have not called for this. Our people have not asked for this, but nevertheless, we find ourselves having to respond to this,” Johnson said before signing the executive order on Saturday.

But the actual executive order (PDF) was somewhat less bellicose, per these quotes from the accompanying press release:

The work of the Protecting Chicago Initiative will include, but is not limited to:

• Ensuring accessible information is made readily available regarding residents’ rights when encountering potential immigration enforcement activities occurring at or near schools, hospitals, homeless shelters, places of worship and other sensitive locations. This information will be developed in direct response to the Trump Administration’s rescission of long-standing policy that prohibited immigration enforcement actions in sensitive areas.
• Directing coordination with Departments and agencies, community, business and philanthropic partners, and the faith-based community, to identify and address community needs resulting from the threats of federal law enforcement and military deployment as well as federal budget cuts that drastically reduce funding for vital programs, including Medicaid and SNAP.
• Regularly submitting Freedom of Information Act (FOIA) requests to the U.S. Department of Homeland Security (DHS), including but not limited to the actions of Immigration and Customs Enforcement (ICE) and Customs and Border Protection (CBP), to obtain information related to federal immigration enforcement activity within the city.
• Cooperating with consular officers serving Chicagoans to document federal law enforcement activity and ensure that residents are exposed to Know Your Rights materials.

Mayor Johnson’s executive order ensures the Chicago Police Department will remain a locally controlled law enforcement agency under the authority of the City of Chicago. The order calls upon all federal law enforcement and U.S. Armed Forces personnel to abide by the policies laid out in municipal law and operational requirements of constitutional policing if they operate in Chicago.

In the interest of community safety and accountability Mayor Johnson’s executive order urges all federal law enforcement and U.S. armed forces commanding offices and personnel who may be ordered to operate in Chicago adhere to the following policies and operational requirements CPD officers uphold everyday:

• In Chicago, law enforcement cannot wear any mask, covering, or disguise intended to conceal their identities from the public while performing their official duties.
• Personnel must legally wear body cameras and activate those cameras during all law enforcement-related activities during which the officer is interacting with a member of the public.
• Personnel must legally display identifying information in a clearly visible fashion. This should include the name of the federal agency, last name, and badge number of the federal law enforcement officer, or the armed forces member’s last name and rank, respectively.

Mayor Johnson also took to the op-ed pages of The New York Times to justify his crime policies and argue that Trump’s military intervention isn’t needed.

Here’s a sample of Johnson’s argument:

For much of the last six decades, Chicago’s leaders have pursued various “tough on crime” strategies targeting guns, drugs and gangs. Despite the significant resources devoted to these strategies, sustained reductions in crime proved elusive.

This is why I push back when people make it seem as though adding an arbitrary number of police officers — or armed soldiers — will solve the problem. If it were that easy, we would have solved the issue of violence a long time ago.

My administration has managed to make progress in crime reduction with three interconnected strategies: effective and law-abiding policing, violence prevention and addressing the root causes of crime.

Johnson is explaining while Trump is acting and seems to be completely missing the point.

Trump doesn’t care about street crime or effective policy responses. Trump is using these military interventions to intimidate Democratic elected officials and residents of blue cities.

For what it’s worth, Johnson’s executive order contrasts strongly with the executive order (PDF) Washington, D.C. Mayor Muriel E. Bowser issued in response to Trump’s federal takeover of law enforcement in her city.

The Hill summarized:

The president and White House communications staff have praised Bowser for her “positive” response to the federal takeover of the district’s law enforcement and the new agreement.

“I’m very proud of Washington,” Trump said after Bowser signed the Tuesday order. “It can be used as a template.”

The measure created the Safe and Beautiful Emergency Operations Center (SBEOC), which is expected to be run by the city and work alongside the president’s Safe and Beautiful Task Force, which was launched in March, to promote public safety.

Agencies involved in the joint operations include the U.S. Marshals Service, FBI, U.S. Park Police, Drug Enforcement Administration (DEA), Bureau of Alcohol, Tobacco, Firearms and Explosives (ATF), U.S. Capitol Police and the U.S. Secret Service.

Bowser said the SBEOC will handle requests submitted to federal partners which include promoting traditional policing practices such as not wearing masks, clearly identifying their agency and providing identification during arrests and encounters with the public.

In fairness to Bowser, her strategy seems to be set on precluding a Congressional emergency act that would extend Trump’s takeover beyond 30 days, via Politico:

“I want the message to be clear to the Congress, we have a framework to request or use federal resources in our city,” Bowser told reporters at a press conference Wednesday. “We don’t need a presidential emergency.”

The federal government has unique and broad powers in the nation’s capital that it doesn’t in other cities. But the Home Rule Act, the 1970s law that gave the city limited self-governance, only allows the president to commandeer city police for 30 days without congressional approval. The mayor’s Tuesday executive order empowers Washington’s new Safe and Beautiful Emergency Operations Center to “ensure coordination with federal law enforcement to the maximum extent allowable by law within the District.”

But as she faces criticism from many city residents — and relative praise from the White House for working with the federal government throughout its surge — Bowser says her executive order is the city’s only way out of an unprecedented period of federal control.

“Let me tell you, without equivocation, that the mayor’s order does not extend the Trump emergency,” Bowser told reporters at a Wednesday press conference. “In fact, it does the exact opposite. What it does is lays out a framework for how we will exit the emergency. The emergency ends on September 10.”

Nonetheless, the optics of Bowser’s response to Trump has drawn local criticism, from the WaPo:

A contingent of D.C. lawmakers and a coalition of 100 local organizations accused her of appeasing Trump and undermining the city’s ability to handle its own affairs after she expressed appreciation for the surge of federal officers on city streets. The criticism only intensified after she issued a directive ordering local police to coordinate with federal law enforcement indefinitely.

…it remains unclear how different D.C. streets will look if Trump’s emergency control of D.C.’s police department expires Wednesday. While the White House would no longer be able to force local police to comply with specific requests, Bowser would still be powerless to stop roadside checkpoints and raids by Immigration and Customs Enforcement agents. National Guard troops are still expected to patrol the city for months.

Bowser’s critics fear her continued collaboration with Trump could further erode the city’s self-government, already limited because Congress has final say over its budget and laws.

No doubt, Trump’s reaction on Truth social has likely upset Bowser’s critics as much as anything:

Wow! Mayor Muriel Bowser of D.C. has become very popular because she worked with me and my great people in bringing CRIME down to virtually NOTHING in D.C. Her statements and actions were positive, instead of others like Pritzker, Wes Moore, Newscum, and the 5% approval rated Mayor of Chicago, who spend all of their time trying to justify violent Crime, instead of working with us to completely ELIMINATE it, which we have done in Washington, D.C., NOW A CRIME FREE ZONE.

Wouldn’t it be nice to say that about Chicago, Los Angeles, New York, and even the Crime Drenched City of Baltimore??? It can happen, and it can happen FAST! Work with us!!! Mayor Bowser’s ratings have gone up, in a short period of time, 25%, and the people of D.C. are thanking her for stopping crime wherever she goes. It’s not a miracle, it’s hard work, courage, and being SMART.

The top Law Enforcement Officer in L.A. said, during the riots, and when I sent the troops in early, that they couldn’t have done it without us. They were completely overwhelmed! If we hadn’t gone in early, on top of the Palisades plus fires, L.A. would have lost the Olympics. Congratulations to Mayor Muriel Bowser, but don’t go Woke on us. D.C. is a GIANT VICTORY that never has to end!!!

In contrast to Bowser, Chicago Mayor Johnson has support from Illinois’ Senatorial delegation and its Governor J.B. Pritzker, who’s bravely taking to social media to voice his opposition:

This is not about fighting crime. This is about Donald Trump trying to intimidate Americans and his political rivals into submission. It will not work, and we won’t back down. pic.twitter.com/Q4lmPIv5mM

— JB Pritzker (@JBPritzker) August 27, 2025

The Chicago Tribune had more on Trump’s plans and Pritzker’s reactions:

n the face of continued and confusing threats that Chicago would be subjected to a federal incursion over immigration and crime, Gov. JB Pritzker on Tuesday sought to brace Chicagoans for a spike in raids from federal authorities and even potentially the National Guard in coming days.

“Let’s be clear, the terror and cruelty is the point, not the safety of anyone living here,” Pritzker said at a downtown news conference, standing alongside Chicago Mayor Brandon Johnson, Cook County President Toni Preckwinkle and other state leaders.

While Trump remained ambiguous — even in his most recent comments Tuesday — about a timeline or the details of a federal crackdown in Illinois, Pritzker made it clear his administration thinks Trump plans to deploy armed military personnel to Chicago’s streets and direct immigration enforcement agents to “raid Latino communities” in the coming weeks.

The deployments would look similar to recent actions the Trump administration took in Los Angeles and Washington, D.C., Pritzker said, citing conversations with unnamed sources and journalists, though he acknowledged the administration’s plans are blanketed in rumors and speculation, and the governor blamed Washington for a lack of coordination.

The governor’s announcement in Chicago came just hours after Trump told reporters in Washington that it was a matter of when — not if — he would send members of the National Guard into Chicago over the city’s crime problem.

“Well, we’re going in. I didn’t say when we’re going in,” Trump told reporters in the Oval Office. “Look, I have an obligation. This isn’t a political thing. I have an obligation when we lose, when 20 people are killed over the last two and a half weeks, and 75 are shot with bullets.”

But Pritzker countered that the move was not only political but authoritarian, adding that he specifically has “reason to believe that the Trump administration has already begun staging the Texas National Guard for deployment in Illinois.”

The Texas Military Department didn’t immediately respond to a request for comment on Pritzker’s remarks, but in a published report in the Houston Chronicle Texas Gov. Greg Abbott’s office disputed the claim.

Yesterday, Trump attempted to clarify his intentions, per ABC 7 Chicago:

President Donald Trump was adamant with reporters on Sunday that “we’re not going to war” with Chicago, after he shared a post on Saturday with a caption that reads, “Chicago about to find out why it’s called the Department of WAR.”

“We’re not going to war. We’re going to clean up our cities,” Trump said. “We’re going to clear them up so they don’t kill every five people every weekend. That’s not war. That’s common sense.”

The White House “Border Czar” says Chicago should expect a surge of immigration enforcement actions this week, and he says the use of National Guard troops to protect and support those operations is “on the table”.

It’s important to remember that this is all taking place in a context of imperial retrenchment and possible retreat from conflicts in East Asia, West Asia, and Europe.

Trump’s deployment of U.S. military resources to American cities is a classic example of Aimé Césaire’s Imperial Boomerang in action.

As Hannah Arendt, among others, used the term to explain the emergence of European fascism following the colonial era, “governments that develop repressive techniques to control colonial territories will eventually deploy those same techniques domestically against their own citizens.”

Simplicius and Bernhard at Moon of Alabama have more thoughts on the imperial boomerang and whether Trump is actually pulling back militarily or not.

The GOP majority on the Supreme Court is letting Trump have his way:

The Supreme Court on Monday cleared the way for federal agents to conduct sweeping immigration operations for now in Los Angeles, the latest victory for President Donald Trump’s administration at the high court.

The conservative majority lifted a restraining order from a judge who found that “roving patrols” were conducting indiscriminate stops in and around LA. The order had barred immigration agents from stopping people solely based on their race, language, job or location.

Justice Brett Kavanaugh said the broad order went too far in restricting how Immigration and Customs Enforcement agents can carry out brief stops for questioning.

“To be clear, apparent ethnicity alone cannot furnish reasonable suspicion; under this Court’s case law regarding immigration stops, however, it can be a ‘relevant factor’ when considered along with other salient factors,” he wrote in a concurrence with the majority’s brief, unexplained order. He suggested that stops in which force is used could yet face more legal pushback.

Regardless, Trump is leading the United States into a post-Constitutional order and chaos is on the menu.

It remains to be seen if and when Trump’s opposition moves from the performative to the kinetic arena.