Chicago has grown accustomed to being a political punching bag. For years, Republicans have used the city’s real problems with crime and corruption as a sort of dystopian shorthand for all that ails Democratic cities.
Mayor Brandon Johnson has cast himself as a counterpoint to that caricature.
In speech after speech, he refers to Chicago as the “greatest freakin’ city in the world.” He once said, “If you don’t live in Chicago, you don’t have a right to talk about the city of Chicago.” And as some expressed trepidation about hosting this week’s Democratic National Convention, Mr. Johnson, 48 and in his first term as mayor, insisted that Chicago was ready, arguing that “there’s nowhere else in this country that could handle the gravity of what we’re experiencing right now.”
Municipal pep talks aside, Mr. Johnson’s first 15 months in City Hall have not been easy. Chicago has struggled to take in tens of thousands of migrants, many of them bused in by Texas conservatives making a political point. Voters rejected a plan the mayor campaigned on to raise tax revenues to address homelessness. And a contentious City Council debate about whether to call for a cease-fire in Gaza exposed divides on the political left, with Mr. Johnson casting the tiebreaking vote in favor of the resolution.
As the Democratic Party comes to town this week — along with journalists, law enforcement officials and thousands of left-wing protesters furious with the Biden administration — Mr. Johnson, who is expected to speak from the main stage on Monday night, believes that this convention has the potential to reframe the conversation about Chicago.
But if things go poorly, it could also reinforce the old, unflattering impressions of a big city run by Democrats. For the mayor, just like for his city, it is a week loaded with opportunity and risk.
A Work in Progress
Mr. Johnson could not suppress the social studies teacher he used to be when city officials and curious commuters this month celebrated the reopening of a long-shuttered train station on the Near West Side, a few blocks from the arena that will host the convention.
“We go all the way back to 1948 when this L stop was shut down,” the mayor told the crowd, sounding a bit like he was launching into a lesson plan. He lamented the decades after the closure when, he said, the area was neglected and ignored. He described the station’s rebirth as “another step in our city’s journey to reverse the historic disinvestment of this community.”
The origins of the construction project predated Mr. Johnson’s election, but the story of the station’s revival fit neatly into the mayor’s view of where Chicago has gone wrong, and how it might move forward.
Mr. Johnson ascended from a little-known Cook County commissioner into the standard-bearer for Chicago progressives in the course of just a few months when he ran for mayor last year. With financial backing from his longtime employer, the Chicago Teachers Union, he placed second in an opening round of balloting, ahead of the incumbent mayor and a sitting congressman. In a runoff, he beat a more conservative and better-known opponent.
As a candidate, Mr. Johnson spoke of disinvestment he saw as a public-school teacher in Cabrini-Green, where he taught students whose public housing towers were being torn down, and in his own neighborhood on the West Side. Fixing Chicago’s problems, he said, started with spending intentionally on people and places that had been overlooked by government.
He dismissed attacks on his ties to the teachers’ union, which had sparred publicly with two consecutive mayors and led its members on strikes, and he brushed off attempts to tie him to the defund-the-police movement. As a county commissioner, he supported a resolution to “redirect funds from policing and incarceration to public services not administered by law enforcement,” but as a candidate for mayor he pledged to hire more detectives.
He also pushed for a proposal to increase the city’s transfer tax on high-value real estate to raise money for homelessness programs. Mr. Johnson’s election helped get that question on the primary ballot this spring, but the timing could hardly have been worse for supporters of the tax.
The tax debate became intertwined with the arrival of thousands of migrants and the struggle by local officials to house them. When city leaders moved to open new shelters, Chicagoans often loudly pushed back. For months, migrants camped outside police stations or on airport floors.
At the same time, the city’s downtown real estate market was reeling from Covid-19 aftershocks. As vacancies piled up, industry groups warned that a new tax would compound the crisis.
Voters rejected the tax, a blow to Mr. Johnson’s agenda.
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Still, for a mayor who entered office already facing deep skepticism from many in corporate Chicago, the issue caused significant damage.
“What we’ve heard from the mayor over the last couple of years has been that, in order to lift up certain parts of the city, in order to do good for the city, we have to do bad for or harm some other segment of the economy or business sector,” said Jeff Baker, the chief executive of Illinois Realtors, a group that opposed the tax increase.
Mr. Johnson said he had worked to develop relationships with the business community and had made real progress in attracting investments.
Nicholas Sposato, a right-leaning Chicago City Council member, described Mr. Johnson as “big-time lefty” and listed a number of issues where the two disagree, including a Johnson-backed panel to study possible reparations for Black Chicagoans. But he said he respects Mr. Johnson’s willingness to hear dissenting voices in meetings.
“He doesn’t cut people off, he doesn’t try to avoid them, which is something that I really appreciate,” Mr. Sposato said.
Walter Burnett Jr., a City Council member who endorsed Mr. Johnson’s opponent in last year’s runoff, said the mayor had grown into the job. Mr. Johnson learned to “become more reserved” in how he talks about some contentious issues, Mr. Burnett said, adding: “He gets it.”
Still, many Chicagoans see work to be done. Lawrence Hill, 66, who runs a nonprofit organization on the South Side, said crime remained a major concern.
“He’s got to figure out a way to get the younger crowd at all these meetings,” Mr. Hill, who voted for Mr. Johnson, said at a recent city-run block party.
Asked to grade his own performance, Mr. Johnson said it was too early but noted that homicides are down, the city has added more detectives and Chicago is phasing out the practice of paying tipped workers an hourly rate below minimum wage.
‘Protector of This Moment’
Chicago cannot host a Democratic National Convention without rehashing the party’s 1968 gathering, when Chicago police officers clashed with antiwar protesters. This year, like then, Democrats are divided over an overseas war. This year, like then, protesters are expected to gather by the thousands.
But Mr. Johnson, who speaks often of his own history leading demonstrations with the teachers’ union, has insisted that the Chicago of 2024 is prepared. He has tried to walk a middle ground between Chicagoans fearful of violent unrest and groups that have filed lawsuits asserting that the city was suppressing their right to protest.
“Having space where protest is protected and safe, that is a requirement,” Mr. Johnson said, adding that “our city will be at the forefront, demonstrating what constitutional policing looks like.”
Still, the county court system is opening extra space in case of mass arrests, and police officers have been training in riot gear. Some office workers are planning to stay home this week, and some residents are leaving town until the convention wraps up.
But while the convention comes with risks, there is a reason cities want to host one. If all goes well, the event will bring revenue to local businesses and show off Chicago’s scenic lakefront, acclaimed restaurants and walkable neighborhoods to visitors who might have heard more about the city’s brutal winters and struggles with gun violence.
“I’m the protector of this moment,” Mr. Johnson said of his place in Chicago’s turn in the spotlight. “My role is to protect the sanctity, the conflict, the beauty and the hope of this moment.”
Mr. Sposato, the City Council member, put it another way. It might not be fair to the mayor, but “he’ll be blamed for it or get the credit for it, whatever happens.”