Johnson, who does not call himself a democratic socialist but believes in many of the same principles as Mamdani, was swept into office by a coalition underpinned by the powerful Chicago Teachers Union and the city’s Black and brown voters. He vowed to unite fractured coalitions and lift up the most vulnerable. He represented change, and his strong roots in the community as an activist, a parent and a resident of a neighborhood that struggles with crime gave hope around new efforts toward equality across a city long deeply segregated by race and income.

The young, energetic activist with a passion for fighting wealth inequality and lifting up the city’s left-behind neighborhoods entered office with much promise. But it hasn’t gone well since then.

“They lost the plot,” the person close to both Mamdani’s and Johnson’s teams said of Johnson’s tenure. The person noted that while both Johnson and Mamdani have specific visions, they said Mamdani is “pragmatic and he wants to succeed” but described Johnson as unbending at times.

One of the most significant missteps, the person said, was whom Johnson brought into his administration, adding: “Staffing is very important. You need professionals who can execute your vision. Those may not be the same people who ran your campaign.”

One of Mamdani’s recent communications hires comes with deep experience. Dora Pekec, who once served as a campaign manager for Chicago Alderman Bill Conway, also worked with House Majority PAC before heading communications for Brad Lander in his New York mayoral run. Former Mayor Bill de Blasio also recently suggested staffers under his administration would be ripe for picking.

It was a point that Rep. Jesus “Chuy” Garcia, D-Ill., also underscored. Garcia was among those who lost in the first round of Chicago’s 2023 mayoral election.

“When progressives run for high office it’s critical to be ready to govern,” Garcia wrote in a text message. “Governing entails striking a balance between promises made (ideals) and making the wheels of government turn. Need to assemble a team that understands your priorities and deliver services, keep relationships with stakeholders especially a base while expanding through engagement. Intergovernmental relationships need to be really keen.”

“Experience in developing and executing plans is most important. This applies to Johnson and when Mamdani is elected,” he continued.

Agendas and obstacles

While attempting to make headway on his agenda, Johnson was confronted with a rash of challenges facing Chicago, and his popularity began to slide. With some exceptions, observers say it was less about Johnson pushing far-left policies and more about the mayor’s confrontational style, his struggles to communicate and his inability to forge alliances with state and federal officials.

Even as he made headway in the areas of public safety and mental health, Johnson grew entrenched in battles big and small, cultivating an air of drama over his City Hall.

While Johnson eschewed criticism during his campaign that he would be owned by the teachers union, those concerns persisted. He did hammer out a teachers contract without a disruption to the school year — no small feat — but it proved to be a bad-tempered and messy ordeal that could bring lasting political reprisal. He went to war with and fired a popular schools CEO, and also saw the resignations of the entire board of education, which Johnson had appointed.

Johnson almost immediately saw his coalition splinter over an influx of migrants whom Texas Gov. Greg Abbott bused into Chicago without warning. Like other major cities at the time, Chicago grappled with how to adequately house families vying for legal status. The city clashed with its own residents, including in neighborhoods of color, with much of the political backlash affecting Johnson.

He and Gov. JB Pritzker, a fellow Democrat, share a frosty relationship at best. He locked horns with his city council over major policy decisions. He broke a campaign promise by seeking a $300 million property tax increase then suffered the humiliation of a 50-0 council defeat.

William Daley, the son of longtime Mayor Richard J. Daley and brother of longtime Mayor Richard M. Daley, said Johnson’s troubles at least partially stem from lacking experience in managing an expansive budget and overseeing tens of thousands of employees. He predicted that, if elected, the 33-year-old Mamdani could face similar political troubles as Johnson.

“It’s a very tough job if you’ve never been in politics or in a job that manages something big,” Daley said, noting his brother’s prior experience before his mayorship. “Rich had eight years as state’s attorney. … He had that experience for eight years — running something. It’s not an easy task for these people who have never run anything.”

Johnson’s predecessors had their own shortcomings, from public corruption to massive civil rights failures, relentless crime and poor fiscal management that still haunts the city today. In 2008, then-Mayor Richard M. Daley sold the city’s parking meters to private investors for a staggering 75 years, trading billions of dollars in future revenue to plug a budget hole for a one-time payment.

Taylor, the Chicago City Council member, said that while Johnson “made some rookie mistakes” he is unfairly getting the brunt of the blame for mistakes shared by predecessors.

“You think in 22 months we have dug a $1.5 billion hole?” she said of those blaming Johnson. “The math ain’t mathing.”

New beginnings

Politically, things have potential to look up for Johnson. Trump has sicced his Department of Justice on the mayor to investigate his hiring practices after Johnson had discussed hiring Black individuals for key positions. Johnson fired back that his hiring reflected the country and the city, while Trump’s hiring reflected a “country club.”

It caught on in conservative circles, with cable news hosts bashing Johnson just as they had done with Lightfoot. In an interview, she said Mamdani could expect the same.

Lightfoot often hit back, and that brought its own repercussions.

“It’s hard to fight against the guy who’s got the biggest megaphone in the world,” Lightfoot said. “Many of us who were Black women, like me in Chicago, like Muriel Bowser in D.C., like Keisha Lance Bottoms in Atlanta, when he mentioned us by name in a disparaging way, candidly, the death threats went through the roof.”

Moving into the second half of his term, Johnson can point to public safety as one of his biggest achievements. Observers largely applaud his choice of Superintendent Larry Snelling to lead the police department, as well as policies the mayor has put into place, like boosting mental health services, restructuring the detectives bureau and backing violence intervention methods.

The number of murders in the city has fallen for two consecutive years, and Chicago could be on pace to reach the mayor’s goal of having fewer than 500 homicides this year for the first time in a decade.

“Mayor Johnson’s primary focus over his first two years in office has been on driving down violent crime in Chicago. Since taking office, Chicago has seen historic reductions in crime and violence under the Johnson administration’s holistic approach,” a spokesperson from Johnson’s office said in a statement, citing a 33% drop in homicides in the first six months of 2025 and a 38% drop in shootings in that same period. It also boasted of having the highest homicide clearance rate in more than a decade.

As far as Johnson’s poll numbers, “the narrative that Mayor Johnson is unpopular has been constructed by a small number of well-funded political organizations opposed to the Mayor’s progressive agenda,” the statement said.