Mayor Brandon Johnson's second year found him fighting unexpected battles

Chicago Tribune

11-05-2025

One recent Sunday afternoon, Mayor Brandon Johnson strode into a scene that seemed tailor-made for shoring up his political base.
The Chicago Alliance Against Racist and Political Repression had convened an audience of grassroots activists and Black faith leaders inside a Far South Side church, where organizer Frank Chapman promised 'a direct response to the attacks on the Brandon Johnson administration.'
But Johnson had hardly smoothed out his prepared notes before a grieving woman began shouting him down over a recent fatal Chicago police shooting. The mayor did not regain control of the room for another five minutes.
'I do recognize that expectations for a Black man are quite profound,' Johnson said after the woman left. 'I'm certainly not intimidated by a moment where our people are expressing their hurt.'
Johnson arrives at his second anniversary in office this Thursday, and his response that day reflected a chief executive who has often endeavored to project strength and temper hopes on what he can achieve by his term's halfway mark.
Though the harsh spotlight on Johnson's office on the fifth floor is nothing new, some of the thorniest issues the former Chicago Teachers Union organizer has battled his second year have come from unexpected fronts: education, and the city's political left. Those difficulties at times dominated his administration's attention and pushed him to expend political capital in ways he may not have predicted when he came into office as the city's most progressive mayor in 40 years.
A bitter feud with Chicago Public Schools leadership dogged Johnson for months. The road to settling a new Chicago Teachers Union contract without a strike grew surprisingly arduous, emboldening opponents to challenge his authority over the nation's fourth-largest school district.
Last fall's bruising budget fight also weakened the mayor's standing with the City Council, including its increasingly disillusioned bloc of progressives who were supposed to be his strongest allies. Those relationship fissures show in the unusual frequency of razor-thin votes and Johnson's stalled progressive agenda.
And the start of Republican President Donald Trump's second term has catapulted Johnson into the national spotlight — and placed the left-leaning city in the crosshairs of a hostile White House.
In an interview with the Tribune, Johnson responded to the seeming chaos under his leadership by arguing the robust debates in City Council and beyond are a sign of a healthy democracy compared to long stretches of near-total mayoral control in Chicago.
'You had an era where there was rubber stamp, and it was absolutely chaotic,' Johnson said. 'Massive school closings, shutting down mental health clinics, dismantling and destroying public housing, disrupting the financial apparatus and stability of our city. All of that chaos happened under rubber stamp. All of it. And what we've been able to do by opening up spaces where people can have real dissent, it's how we're able to move the city forward.'
He went on to stress the magnitude of what he 'inherited.'
'Certain parts of the city, we're still excavating the rubbish and the ashes from the dismantling and disinvestment in our neighborhoods. And so I share that frustration,' Johnson said. 'The things that I have wanted to do, I've not been able to do them as fast as I would like.'
But whether City Hall is experiencing 'real dissent' or actual chaos, the question the mayor faces at his midterm is how much more can Chicagoans — and Johnson's progressive base — tolerate before losing patience and laying the blame squarely on him rather than his predecessors?
Johnson perhaps pulled out no stock response in his second year more frequently than 'I don't discuss personnel issues.'
The mayor has trotted out the catchall answer throughout his high-profile clashes with city officials and controversies over top deputies in his administration. In September, that strategy of keeping administration problems in-house notably buckled once news outlets reported the mayor called for CEO Pedro Martinez to resign, a demand the schools chief rebuffed.
Johnson later denied that he told Martinez to step down but has avoided saying what actually transpired during their meeting. Asked why he didn't prioritize getting out in front of the narrative, the mayor said he doesn't believe in disclosing private discussions.
'There's conversations that have happened in these walls for generations,' Johnson said, referring to City Hall. 'There's something sacred about that. When I was asked directly was it true or not, of course I had to speak the truth. But I'm not going to go into details and break confidence and trust.'
But outside the media spotlight, the mayor showed a more forceful side when confronting other city leaders over Martinez's defiance.
A former Chicago Public Schools official told the Tribune that a week after Johnson and Martinez's meeting became public, the mayor called to ask for that ex-official's help in pressuring the CEO to resign. That person, a Martinez ally who asked to remain anonymous to discuss a private conversation, said no.
An alderman also publicly defended Martinez as rumors of the mayor's wishes to replace his schools chief surfaced. According to the council member, who also asked to remain unnamed, Johnson later challenged them at an event last year: 'Every mayor in Chicago history has been able to pick their schools chief. Why can't I?'
Johnson's office did not respond to questions about the conversations. But his nonetheless clumsy efforts to oust Martinez illustrate a recurring theme throughout Johnson's stunning battle for control of CPS — and of Chicago's broader progressive labor movement.
A product of the grassroots coalition that fought to weaken the exact office he would one day occupy, including by fighting for an elected school board, Johnson has appeared caught off-guard in moments when his power was questioned.
That showed in the October mass resignations of his first handpicked school board, a remarkable flashpoint in Johnson's dispute with Martinez that centered on district finances, and condemnation from a broad coalition of officials — including Gov. JB Pritzker and 41 of 50 aldermen — over Johnson's maneuvering during the waning days of mayoral control of CPS. The mayor at last clinched a CTU contract in April. But his still-unfulfilled goal for the district to issue more debt to cover a disputed pension payment and the start of the teachers' raises has fueled further attacks that he is beholden to his former employer and not the city.
And while Johnson is correct that he has the authority to hire and fire who he chooses — with the caveat of needing board or council approval for some positions — he has presided over several messy exits.
Asked whether that is an area of being the executive that he struggles with, Johnson said that 'gives me something to think about' and acknowledged there are different methods of firing staffers.
'Many people have not stayed here,' Johnson said. 'There are folks who have been dismissed, and no one ever knows about it.'
Ald. Jeanette Taylor, a Johnson ally who has said the progressive movement was 'not ready' for the mayor's seat, wants Johnson to know 'You have more allies than you think.' At the same time, she said she believes it's difficult for the mayor to continue feeling out who he can trust in the cutthroat arena of Chicago politics when he is held to a different standard because of his race.
'I just feel like as a Black man being in politics, he's not trusted,' Taylor said. 'We won't give him time. And to be honest, the position doesn't give you time. You got four years. Not six, not eight.'
Earlier this February, as Johnson's opponents pounced with renewed attacks on his leadership abilities, the mayor vowed a purge of disloyal appointees in his administration in one of his most explosive public comments yet.
Behind closed doors, the mayor has faced hurdles with recruiting candidates to fill his top vacancies.
Last fall, Johnson's team interviewed former Cook County state's attorney candidate Clayton Harris for an important role in the mayor's office, a process that appeared to frustrate Kim Foxx during her last days as Cook County's top prosecutor.
'I'm told there was still no call,' she wrote to Johnson in a Nov. 25 text message obtained by the Tribune via a public records request. 'I urgently responded to you, made the outreach, and followed up. If you've changed direction let me know as soon as possible so that I may tell him. … I feel terrible that he's been waiting.'
Foxx declined to comment, but sources said she was involved in connecting Harris with the mayor's office.
Harris ultimately turned down the Johnson administration role and accepted an offer to become Illinois House Speaker Emanuel 'Chris' Welch's chief of staff.
The mayor's permanent selection to helm the Chicago Transit Authority after embattled President Dorval Carter stepped down in January has also lagged for months, even as the mayor's office quietly conducted a nationwide search for candidates but appeared to come up short.
State Rep. Kam Buckner, a 2023 mayoral candidate who hitched much of his platform to the idea of improving public transit, was offered the job but turned it down, according to sources familiar with his decision.
Last week, speculation resurfaced that Johnson plans to tap his chief operating officer John Roberson as his next transit chief, and that his chief of staff, Cristina Pacione-Zayas, was being considered as his next interim CEO of CPS.
The mayor moving his top deputies out of his administration would be a major shakeup, one that signals just how small his inner circle of trusted advisers has become.
Johnson swatted away the assumption that his administration has a talent recruitment problem, saying 'we're not transforming a city in the way in which we're doing it without talented people,' while touting the diversity of his staff.
Other cabinet vacancies he has yet to announce permanent replacements for include the Chicago Housing Authority, Department of Family and Support Services, comptroller and deputy mayors for education and labor.
The mayor has also taken hits to his leadership credibility after a series of mini-scandals surrounding some of his top advisers and appointees.
Ronnie Reese, Johnson's former communications chief, was fired in October after a groundswell of harassment complaints, which he has denied. The mayor has said he didn't know about the allegations at the time.
Johnson's chief of staff, Pacione-Zayas took heat for how she responded to staffers who reported Reese's behavior, including by allegedly suggesting 'peace circles' with him.
Asked whether she should lead CPS given the backlash, Johnson praised her resume in education and in leading the city's migrant response, then asked 'Are we perfect? We're human.'
'And we continue to be humbled by this position, but it doesn't cause us to cower or fret or panic in the midst of controversy,' he said.
As criticism over how Johnson ran both his office and budget negotiations swirled at the end of 2024, Cook County Commissioner Tara Stamps sent him a text that demonstrates how a close ally viewed the churn of negativity.
'You (sic) running the whole city,' Stamps wrote. 'At this point you're being blamed for cold weather in December in Chicago.'
As he waited near the porcelain sink of the bathroom outside City Council chambers, Ald. Desmon Yancy splashed water on his face.
The Progressive Caucus freshman had stepped out of the February meeting to dodge a vote on a highly contested $830 million infrastructure bond plan the mayor was pushing hard to pass. Yancy believed the borrowing terms were possibly too back-loaded and warranted further discussion, but the mayor's top aides were pressing him, he told the Tribune.
'It was a moment of frustration that felt a little bit like the movie 'Groundhog Day,'' Yancy said about walking away during the vote. 'Another one of these moments that felt dismissive of the people who needed to vote for it.'
Moments afterward, Johnson texted the South Side alderman 'Yo' — a clear 'call me' signal. But the two didn't end up talking that day.
Instead, Yancy, already frustrated by Johnson's legislative processes, blasted the mayor in a Chicago Tribune op-ed the next week. 'Dissenting voices are consistently shut down,' he wrote. 'Detractors are shut out. Advice is ignored.'
The alderman said he did not hear from the administration on his criticism until Johnson called weeks later, saying he did not read the op-ed and hoped the two could find a path forward.
Yancy's far from the only progressive whose relationship with Johnson has suffered.
'The writing is on the wall,' said progressive Ald. Ruth Cruz, who declined an invitation to join Johnson's new budget working group. 'The council is becoming stronger. More opposition will come. Trust is fading away. Something big needs to happen to turn the page.'
Indeed, Johnson's legislative agenda has scarcely budged in recent months. His team began the year with a first-quarter agenda of tackling legislation for the city to tax and regulate hemp, reform Chicago police no-knock warrants, create a revolving loan fund for affordable housing and tighten environmental regulations on polluters.
As of now, only the housing loan fund has come to fruition following passage in last week's City Council meeting — just in time for Johnson to point to a legislative victory in his two-year anniversary media appearances.
Johnson has challenged the notion that he isn't moving fast enough. His usual rebuttal includes touting the continued decline in violence that he partly attributes to him boosting the city's youth summer jobs program and community intervention programs as well as upcoming development projects on the South and West sides. Most of his policy victories are from his first year, however, when he enjoyed a honeymoon of sorts and there was more momentum behind his progressive vision.
That includes allocating money to reopen two of the city's shuttered mental health clinics, passing a $1.25 billion bond plan for affordable housing and economic development, bolstering paid time off requirements for Chicago workers and abolishing the subminimum tipped wage.
Johnson said he needs to more effectively communicate his achievements and to 'make sure that we're standing up the very coalition that elected me.'
'There's nothing surreptitious about my administration,' Johnson said. 'What I have to do a better job at is engaging City Council members more frequently and earlier. And we're doing that.'
Amid his shifting relationship with progressives, the mayor has leaned on aldermen in the council's more ideologically diverse Black Caucus to steer legislation, just as he has upped efforts to speak directly to Black residents on the South and West sides. And with a bloc of about a dozen aldermen sturdily opposed to virtually every major legislative push Johnson makes, the result has been a steady stream of close votes, including three tie-breakers — a troubling sign for the mayor's long-term ability to enact legislation.
'The easiest way to get to 26 votes is to get along with 49 other colleagues. So why would I view it as a binary, where I shouldn't talk to so-and-so because we don't agree?' said Ald. Andre Vasquez, the most vocal Johnson critic among the council's political left. 'You don't create a bubble, no matter what.'
Meanwhile, some aldermen are already mobilizing to take the reins of what they see as a directionless body. During the last budget cycle, a bloc of left-leaning and moderate council members began to meet regularly to hash out their own path on the city's spending plans — a group Vasquez once coined 'the sensibles.'
Besides the North Side alderman, those who have participated include Aldermen Matt Martin, Maria Hadden, Nicole Lee, Pat Dowell, Timmy Knudsen, Bennett Lawson, Gilbert Villegas, Samantha Nugent and Bill Conway.
'We were trying to be the adults in the room,' Villegas said. 'If the mayor is not going to lead, then we're going to lead. There's a void. We're going to fill it.'
In fact, some of the 'sensibles' were together at O'Shea's office during November budget discussions when the mayor, during a news conference that was streaming live on an alderman's phone, gave a curious explanation on why he floated a whopping $300 million property tax hike.
'As a public school teacher, sometimes we do things to get people's attention,' Johnson said, to disbelieving head shakes and mutters in the room of aldermen who found his answer patronizing.
The classroom-instructor analogy manifests in other ways the mayor comports himself with the legislative branch. His calendars show he holds regular 'office hours' for aldermen to get face time, an approach that also offends some City Council members who maintain they are a coequal branch of government.
'He's more like the substitute teacher,' persistent mayoral critic Ald. Raymond Lopez said. 'He can't control the room like a real teacher trying to control the classroom.'
There have been several flashpoints where Johnson appeared to overestimate his leverage with the council. Last summer, Ald. Bennett Lawson told the Tribune, the mayor called to ask for his support in confirming Ald. Byron Sigcho-Lopez as Zoning Committee chair and provided the short explanation, 'It's my decision.'
That was despite the administration needing Lawson's help as interim Zoning chair to pass an ordinance allowing for more accessory dwelling units in the city. Neither that legislation nor Sigcho-Lopez's appointment came to pass.
'Respect should go both ways,' Lawson said. 'While I didn't expect to be appointed Zoning chair, I also didn't expect a demand to support a very unpopular pick — a pick that I knew would also be rejected by a majority of my council colleagues.'
But to allies of the mayor, the opposition Johnson has faced — often from moderates, and increasingly from progressives — seems to be motivated by something else.
'It seems like people are against things just to be against things,' said Vice Mayor Ald. Walter Burnett, who ultimately became Johnson's next Zoning chair. 'I think it's holding up the city. I really do think that whatever is happening in the city right now is not just on him, it's on all of us.'
Burnett, who has served under four mayors, said none has faced as much City Council dissent as Johnson. Part of the council's new authority-challenging spirit comes from the union activist philosophy the mayor has imparted, the alderman said. But the increasingly raucous council's pressure has not swayed Johnson, he added.
'I don't think the mayor is politicking. I think the mayor is trying to govern,' Burnett said.
Chapman, the community organizer, argued Johnson has done 'remarkably well' despite the opposition he faces. He praised the mayor's efforts to take more community input into policing, and contended progressive council members now putting distance between Johnson and themselves were 'never with him.'
'Can he do better? Yeah, but we got to get behind him and make him do better,' he said. 'People need to stand with him.'
The mayor must focus on 'mending fences' in his labor coalition and remaining a 'pillar' in the resistance to the federal government, Chapman added.
Indeed, tensions have not fully abated between two of Johnson's biggest union backers. A split over representation of special education aides drove a wedge between CTU and the Service Employees International Union that has yet to be smoothed over.
And Johnson's plans for the next two years will face significant political and financial headwinds with Trump back in the White House.
The second Trump administration has made clear its plans to cut federal grants, especially to cities that promote diversity, equity and inclusion practices or 'sanctuary' laws protecting immigrants from deportation. The mayor went to Washington in March to testify in a congressional hearing over the latter policy, in a by-the-script performance that earned him nods for avoiding any pitfalls on the national stage.
During April budget briefings with aldermen, Johnson administration officials flagged 50 of the president's emergency orders that could jeopardize the $3.5 billion in federal funds Chicago relies on for infrastructure, homelessness support, addressing gun violence and public health.
Those potential cuts come on top of a 2026 deficit that 'without question' will be bigger than last year's $1 billion estimate, said Justin Marlowe, director of the Center for Municipal Finance at the University of Chicago.
'Absent some change in the way they're willing to play the politics of this, they are in much worse shape than they were a couple budget cycles ago and in much worse shape vis-a-vis other big cities,' Marlowe said.
Meanwhile, the sharks are circling at home, two years before Johnson is up for reelection.
Chicago Forward, the business-backed group launched to fight the mayor's failed Bring Chicago Home tax referendum, 'will continue to operate and work to defeat' the city's Democratic socialists, said Greg Goldner, a political consultant with the organization. Another group, the dark money Common Ground Collective, has amassed $10 million and begun targeting progressive aldermen closely aligned with the mayor.
It's an early shot that could dramatically shift City Council dynamics. But it also gives Johnson a clear target and a way to frame his political opponents. And the mayor has zeroed in on it, promising he is 'not going to back down from millionaires and billionaires.'
In another sign Johnson antagonists are preparing to make any instance of supporting his agenda politically toxic in the 2027 election, Illinois Comptroller and potential mayoral candidate Susana Mendoza pounced at a February fundraiser on not just the mayor but the council members who backed his $830 million bond plan.
'Everybody else that voted no, thank you,' Mendoza said in her speech at the Neighborhood Building Owner's Alliance event, praising aldermen in the room who opposed the bond. 'And if you voted yes, shame on you.'