Over the past decade, the job description for the mayor of Chicago has included a new duty: responding to Donald Trump.

The question before Brandon Johnson is, how does the freshman mayor come out on top against a reality TV-bred GOP president made famous for breaking the rules?

Mayor Rahm Emanuel took a typically combative approach, kicking off his relationship with the White House by mocking Trump’s fixation with the crowd size at his 2017 inauguration.

Emanuel’s successor, Lori Lightfoot, went with political theater when she sought to upstage Trump’s new Chicago director of U.S. Immigration and Customs Enforcement in 2019 by hastily calling a dueling news conference outside the agency’s downtown office.

Now, Johnson must chart his own playbook on how to stand up for the city’s liberal values against a Republican president who has pointedly attacked Chicago for years.

Johnson is doing so on the fly during the early days of a second Trump term that’s already disrupted Chicago with a dizzying array of immigration raids targeting area residents and White House orders jeopardizing funding for local projects and more.

So far, the progressive chief executive of America’s third-largest city appears to be walking a fine line between using the fiery underdog rhetoric that boosted his political star and navigating the dangers of antagonizing an unpredictable president.

The mayor’s public remarks these past two weeks suggest that his messaging strategy remains fluid — a reflection of the times.

“That White House is being ran in one of the most raggedy forms of government that I’ve ever seen,” Johnson told reporters Wednesday. “If anybody is questioning whether or not what our country would look like had the Confederacy won, there should be no question now. They want us to be afraid. Do not be afraid, Chicago.”

At a news conference a day earlier, the mayor hedged his comments more and avoided personally attacking Trump, suggesting some degree of wariness over being too confrontational.

Asked his feelings on Phil McGraw, the television personality known as Dr. Phil, shadowing last Sunday’s immigration enforcement blitz in Chicago, Johnson called the event “abhorrent,” but only after suggesting his aides would not appreciate his sharp tone: “Look, my communications team, right, they’re not going to be happy with me right now. I know that.”

Chicago mayors, much like the constituents they serve, are known for their big, tough personas. But Johnson’s role may be more precarious given that the Republican Party controls all three branches of government in Washington.

Moreover, Trump now has more experience in office and is unfettered by reelection pressures because he is term-limited.

“There’s very little that any leader today can take from leadership that saw a much more subdued Trump in 2016,” Ameshia Cross, a Democratic strategist from Chicago, said about Johnson’s approach. “This is Trump without any guardrails, and I think that people have to recognize that. So (Johnson’s) rhetoric matches the moment he happens to be in. Rahm didn’t get this Trump, and Lori Lightfoot didn’t get this Trump.”

Meanwhile, some moderate and conservative leaders in Chicago are imploring the mayor to assist the White House in arresting immigrants charged with or convicted of crimes in hopes of sparing Chicago’s larger community of noncitizens living in the U.S. without legal authorization.

“The refusal to acknowledge that some migrants are committing criminal acts in our city and should be deported is why the whole immigrant community is on edge,” said Ald. Silvana Tabares, a mayoral critic who represents a majority-Latino Southwest Side ward. “We need to send a message to the Trump administration that not all migrants are fair game.”

Ald. Carlos Ramirez-Rosa, a Johnson ally, countered it was naive to believe Trump would show mercy to a city that’s been a punching bag for conservatives.

“This has been a longtime political strategy to target Chicago, and I don’t think that there’s anything that any mayor or any elected official could do at this point from the local level to get Donald Trump to change course,” the Avondale alderman said. “Brandon Johnson as our mayor has done such a good job of defending the people of the city of Chicago that Republicans in Congress are now targeting him.”

However Johnson opts to proceed, he is already shaping up to be a lightning rod for GOP criticism on liberal leadership.

Last week, U.S. Rep. James Comer, R-Ky., requested Johnson and other Democratic mayors testify before the House Oversight Committee in his investigation into sanctuary city policies. Illinois and Chicago laws prohibit local law enforcement from assisting federal immigration authorities. The week before, the Justice Department issued a memo threatening to prosecute local officials resisting Trump’s immigration crackdown.

Then there’s the local landscape. Johnson’s first year as mayor saw him preside over a grueling migrant crisis that inflamed racial tensions in a long-segregated city. Though the Johnson administration ultimately prevailed at tamping down the humanitarian crisis, he weathered months of criticism from leftist activists and Black Chicagoans, two of his political bases that would be critical to a 2027 reelection bid.

Johnson’s latest messaging on Trump’s vision for mass deportations reflects an attempt to bridge that divide.

While remaining unequivocal in stating that Chicago’s sanctuary city ordinance remains “the law of the land,” Johnson often seeks to highlight a broader focus on “working people” in his answers on Trump. He has pivoted from immigration questions by attacking the president’s earlier vow to abolish the Department of Education or his inaction on affordable housing investments — topics seen as important to Black Chicagoans.

“I’m proud that we are a strong, working-class city,” Johnson specified Tuesday when asked whether he was proud enough of Chicago’s sanctuary city status to defend it before Congress. “If I did specify that we are proud to be a welcoming city, I still mean that, but what I really was hoping to come across, (is) that we’re proud of our rich history in the city of Chicago.”

The next day, the mayor began an answer about Trump by noting “there are people who have not accepted the results of the Civil War” and deflected inquiries on whether he would testify in the GOP House probe by asking why Republicans won’t instead hold a hearing on “how reparations can transform people’s lives.”

“If they want to have a real discussion about undocumented individuals who are criminals, they should look at the very individuals who enslaved my people and colonized this land,” Johnson said.

Cross, a South Shore native, said it’s smart for Johnson to make sure Black Chicagoans — “the ones that got him elected” — are not left out of the conversation on Trump’s impact because immigration is “not their primary concern. It’s whether or not they can keep food on the table.”

“Mayor Johnson’s biggest strength is going to be his advocacy and his support of the communities that are currently being pitted against each other,” Cross said. “The people who Mayor Johnson is going to have to align and really strengthen his force with are the Black communities who are feeling the angst and the burn of an economy that has not necessarily benefited them.”

Johnson won the 2023 mayoral election with backing from Black voters and went on to secure key alliances with influential African American aldermen upon assuming office. At the same time, the migrant crisis and other issues such as the gunshot detection service ShotSpotter have driven a wedge between him and moderates in the Black Caucus.

Ald. Anthony Beale said, “Hell no,” when asked if Johnson’s rhetoric on Trump was being well-received in his majority-Black ward on the Far South Side. The frequent Johnson opponent said he worries the harsh criticism from the mayor would cut off federal money from Washington — resources his constituents need.

“Until our people feel like they’re being put first, it’s going to be bad news every single day,” Beale said. “I don’t think (Johnson’s) being much of a politician. I think he’s still in activist mode, and it’s hurting the city.”

Brighton Park Ald. Julia Ramirez disagreed: “I don’t really think about what the mayor should not speak on.” She and other progressive Latino colleagues representing wards targeted by ICE last weekend praised Johnson’s approach thus far.

“There are very intentional attacks from people that really just don’t give a s— and he’s going to bear that,” Ramirez said. “I think we should really be critical about what the president is trying to do.”

In some ways, Johnson has been less visible in the opposition against Trump than prior Chicago mayors. He avoided holding any news conferences the first week Trump took over, and he did not make any advertised stops in Latino communities until his Wednesday media availability in the Puerto Rican enclave of Humboldt Park.

Meanwhile Gov. JB Pritzker, a rumored hopeful in the 2028 presidential race, posted the afternoon of Trump’s inauguration: “Checking in, Illinois. Started the day off strong in Little Village today with a concha and coffee.”

Lightfoot also personally passed out “Know Your Rights” flyers and walked 26th Street in Little Village, the heart of Chicago’s Mexican immigrant community, when Trump threatened ICE raids during her first months in office.

Johnson dismissed what he described as “the dramatic presentations that people seem to fawn over” in an interview with the Tribune shortly after the White House transition, suggesting his team doesn’t see much value in matching Trump’s energy. The goal, the mayor later told reporters, is to project “calm leadership.”

That’s a wise play, said Northwestern University professor Jaime Dominguez, who specializes in Latino politics.

“I think that Brandon Johnson’s rhetoric has somewhat tapered a bit because of the fact that as the chief executive of the city … the way to quell or to neutralize that anxiety is by remaining calm,” Dominguez said. “He has to project that he’s stoic.”

Outside the public spotlight, the mayor has focused on using his City Hall force to inform communities facing deportation threats of their rights and ensure Chicago police continue to not cooperate with ICE. A wide array of aldermanic offices, political groups and immigrant advocacy nonprofits have worked hand in hand with Johnson’s team to spread awareness on navigating ICE encounters.

The campaign has included community meetings, flyer postings and advertisements throughout the Chicago Transit Authority system. So far, it’s apparently made a difference, much to Trump “border czar” Tom Homan’s chagrin.

“They call it ‘Know Your Rights.’ I call it ‘How To Escape Arrest,’” Homan told CNN last week about the pamphlets he’s seen in Chicago.

At the same time, the Trump administration has made his immigration crackdown into a reality show of sorts, with McGraw and a camera crew shadowing last Sunday’s ICE raids. Meanwhile the local rumor mill has occasionally further exacerbated anxieties, giving credence to a “wait-and-see” approach.

On Jan. 24, Chicago Public Schools leadership announced an ICE visit at an elementary school before walking it back, while the mayor’s office stayed mum until hours after it was reported the agents were in fact U.S. Secret Service. Johnson’s deputy mayor Garien Gatewood told reporters the next week: “This is why we waited to make sure we verified information before information was out.”

Of course, Democratic politicians have much to gain from confronting Trump, particularly in deep-blue Chicago.

Emanuel’s last mayoral campaign in 2015 saw him blast ads tying one challenger, former Chicago police Superintendent Garry McCarthy, to the then-rising GOP presidential candidate as local controversy over the CPD murder of Laquan McDonald mounted.

One of Lightfoot’s main political liabilities — her struggle to get along with other leaders — became an asset whenever she took Republicans to the mat for criticizing Chicago.

Johnson is primed to see his own political brand as a firebrand progressive regain momentum after a rocky two years. His bruising 2025 budget cycle, recent scandals surrounding his top officials and his spat with the lame-duck CPS CEO leave his standing with the City Council at a nadir. His progressive agenda has stalled, and his calls for more state assistance continue being dismissed by Springfield leaders including Pritzker.

The mayor has often reacted to setbacks defensively, ignoring warnings over his shrinking coalition by entrenching himself further with the progressive labor and Black faith supporters who have proved his most loyal. But with Trump now animating all stripes of Democrats, Johnson seems to be already capitalizing on openings to position himself as a liberal foil to Trump — and deflect from his own liabilities.

That was on full display during Johnson’s Wednesday media availability that came on the heels of an inspector general report that found his office violated ethics rules on using a public log to report gifts his office received.

“Look, I know folks want to talk about gifts to the city, but we have an individual who is president of the United States of America who is behaving under the same guise of other dictators,” Johnson said. “The real threat to our democracy, it’s not a log. The real threat to our democracy is an individual who believes that he’s above the law.”

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