When Chicagoans chose a paid organizer for the Chicago Teachers Union and Cook County Commissioner as their 57th mayor, many knew Brandon Johnson would need to grow into the job.

They were right.

Johnson’s first year in office has been a rollercoaster ride filled with the ups of having delivered on a checklist of progressive promises — and the downs of managing contentious relationships with Gov. J.B. Pritzker, the Illinois General Assembly, the business community and police.

There’s even mounting tension with a City Council emboldened by the political weakness Johnson showed by failing to deliver on his signature promise to secure a new revenue source to combat homelessness.

In an interview with the Sun-Times and WBEZ, Johnson reflected on what he called his “remarkable journey” to the mayor’s office and the very “different trajectory” he followed to get there.

He’s proud of having fulfilled so many items on his progressive to-do list and described a year of accomplishments tempered by impatience.

“There are frustrating moments that I do have where you… just wish you could address everything at the same time,” Johnson said. “That’s just unfortunately not where we are — just because the damage has been so severe and it has been so widespread,” especially in “historically marginalized” communities after “40 years, at the very least, of real serious neglect.”

Johnson acknowledged that he hasn’t made everybody happy, but that comes with the turf.

“If the role of the mayor is to satisfy everyone, then we would not have had 56 prior to me,” Johnson said.

Migrant crisis missteps

From the beginning, Johnson has been dogged by the migrant crisis he inherited. One of his first council meetings included a cathartic vote on $51 million in surplus funding for the crisis. It featured a contentious, “us-versus-them” debate that reduced one alderperson to tears.

Johnson’s handling of the migrant crisis telegraphed the freshman mayor’s growing pains. He unveiled plans to open a winterized base camp at a contaminated industrial site in the Southwest Side’s Brighton Park neighborhood only to have Pritzker reject the idea amid environmental concerns.

The local alderperson, a progressive ally, felt blindsided by the mayor’s plan and was subsequently physically accosted by furious constituents. The abandoned plan ended up costing Chicago taxpayers nearly $1 million.

But Johnson succeeded in emptying Chicago police station lobbies filled with asylum seekers and returning park district field houses to their intended use. He did that by opening brick and mortar shelters at a furious pace. At its peak, there were 27 shelters with more than 14,600 migrants and another 800 camped out at police stations, O’Hare and the city’s landing zone.

“When I stepped into office… you had contracts that were bloated and it was costing the taxpayers an enormous amount of dollars without understanding the real benefit in the mission. We’ve transformed all of that… We’ve saved the taxpayers over $200 million dollars…We’ve literally built something that has never existed before,” Johnson said.

But the biggest shelter in Pilsen was crowded and unsanitary, and a 5-year-old boy died of sepsis. The same shelter was subsequently the epicenter for a measles outbreak.

Aldermen are now pushing back on the mayor’s 60-day eviction policy — which was delayed three times and has already forced more than 650 people from shelter.

Johnson also stumbled by initially reneging on a deal with Pritzker and Cook County Board President Toni Preckwinkle, one of his political patrons, to provide $70 million in additional city funding to support migrants through 2024.

His first budget included just $150 million in funding he knew would last only until April 1. He deliberately low-balled the figure to put pressure on the federal government, but the tactic failed.

At one point he used $95 million in federal stimulus to slap an end-of-year Band-Aid on the migrant crisis. But that alienated some aldermen who control spending and were not consulted.

Johnson’s hand-picked chair of the council’s Immigrant and Refugee Rights Committee has frequently complained about being shut out of conversations around the migrant crisis, including about the mayor’s eviction policy. Ald. Andre Vasquez (40th) eventually strong-armed the administration into publishing regular data on evictions.

“There needs to be some work done, as it relates to transparency and accountability as well as cooperation and engagement and dialogue with the alders,” Vasquez said. “It’s about figuring out how to engage with everybody.”

Alderpersons’ grievances with Johnson were on full display at the last Council meeting where they called for the mayor to be more forthright about migrant funding and equal spending on long disinvested communities.

Even after the griping, the Council ultimately passed two of Johnson’s top spending priorities, including $70 million from city reserves for migrant spending to honor the deal with Pritzker and Preckwinkle. Preckwinkle helped by lobbying behind the scenes.

“I know how to count and both those votes received more than 30 votes from City Council,” said Workforce Development Chair Ald. Mike Rodriguez (22nd). “That sounds like a win to me.”

After closing nearly a dozen shelters amid declining numbers, Johnson said he’s “preparing” for a possible influx of migrants in the run-up to the Democratic National Convention in August. But he said there are “limitations to what we can do” without more federal help. He ruled out a return to the base camp idea.

Progress on progressive wish list

Johnson’s legislative successes have been impressive.

In the first year alone he has: phased out the subminimum wage for tipped workers; pushed through the most generous paid leave policy in the country; reinstated the city’s Department of Environment; and laid the groundwork to reopen two of the city’s shuttered mental health clinics.

The mayor has also begun to ease the pressure on Chicago police officers by expanding a plan that sends mental health providers, instead of police, to non-violent mental health emergencies.

Johnson kept his promise to put a binding referendum on the ballot that would have authorized the City Council to raise the real estate transfer tax on high end property transactions to create a dedicated funding source for homelessness prevention. But Chicago voters rejected it, a major defeat widely viewed as a referendum on the mayor’s first year in office.

Mayoral allies in the progressive caucus heard the message loud and clear and vowed to work harder to win the trust of voters and simplify a complicated referendum that many voters didn’t understand.

“Ignoring what those critiques are and thinking that we’re just morally right isn’t going to lead to future wins,” Vasquez said.

At the time, Johnson responded to the defeat with bravado. He warned anyone who might assume that one defeat would make him put the brakes on his progressive agenda to “buckle up.”

More recently, the mayor won Council approval for a $1.25 billion bond issue that will ease the city’s longstanding addiction to tax incremental financing. Former Mayor Lori Lightfoot devised the plan; Johnson embraced it. The same goes for Lightfoot’s plan, which Johnson expanded, to transform nearly vacant buildings along LaSalle Street into more affordable residential units.

Canceling the city’s contract with the gunshot detection technology company known as ShotSpotter also delivered on a progressive promise. Johnson and his base have long viewed ShotSpotter as a surveillance tool that leads to over-policing in Black and brown communities.

But the way Johnson delivered that news somewhat overshadowed the accomplishment.

Johnson announced his decision just days before the contract’s expiration, then had to scramble to negotiate an extension that would carry Chicago through historically violent summer months and the Democratic National Convention.

Shotspotter and the broken migrant funding promise with Pritzker and Preckwinkle were the subject of a disastrous Feb. 15 City Hall press conference that showcased a communication problem that has dominated his first year in office.

That day, as before, he evaded some questions, preferring to answer in platitudes, and wouldn’t say if he had walked away from a funding deal with Pritzker and Preckwinkle or nailed down the Shotspotter extension before announcing a phase-out.

That defining moment in his relationship with the press seems to have led to a course correction. Johnson finally named a permanent communications director in Ronnie Reese, who had essentially filled the role since Johnson took office. Johnson also hired a chief strategy officer, Joe Calvello, who learned the art of being “radically open and honest” while guiding U.S. Sen. John Fetterman (D-Pa.) through a difficult campaign dominated by health issues.

The changes appear to have made an impact already, persuading Johnson to take media questions more often and answer those questions a bit more directly.

Mixed bag for business

Johnson’s aggressive agenda early on put him at odds with a business community hit with two costly mandates — phasing out the subminimum wage for tipped workers and a paid leave policy that’s one of the nation’s most generous.

But labor leaders said Johnson displayed a willingness to work toward a compromise on paid leave and the subminimum wage, while the same business groups that helped defeat the real estate transfer tax referendum kept “moving the goalposts.”

“They were looking not to compromise. They’re just looking to stop the policy. And that’s not realistic,” Chicago Federation of Labor President Bob Reiter said, noting similar policies have been adopted by other major cities.

“They can’t stop that kind of progress.”

Johnson also appeared to extend an olive branch with his recent rollouts of pro-development policies.

He greenlit and expanded Lightfoot’s “LaSalle Street Reimagined” plan; proposed a slew of recommendations to cut bureaucratic red tape on business development; and cleared the long-stalled O’Hare expansion project for takeoff by hammering out a cost-cutting deal with the major airlines.

Johnson has also held the line on city property taxes – even as he has allowed Chicago Public Schools to boost property taxes to their maximum limit two years in a row.

“It’s been a little bit up and down. Some positives. Some negatives,” Chicagoland Chamber of Commerce President Jack Lavin said of Johnson’s first year.

Lavin said there is “a lot of work to be done to improve communication” and trust between the mayor and the business community.

“He has a tax agenda. We have ideas on how we can grow the economy. And we’re going to have to come together because federal money is drying up. There’s lots of fiscal cliffs and fiscal challenges coming up,” Lavin said.

“He’s the mayor. We’ve all got to work together. If the mayor is not successful, Chicago’s not going to be successful.”

Johnson has displayed financial acumen by continuing a Lightfoot policy to make additional payments on the city’s underfunded pension system. But a pension working group Johnson announced early on has yet to produce any ideas on how to solve the $35 billion crisis. Two of four city employee pension funds are hovering perilously close to insolvency.

The business community applauded Johnson’s appointment of seasoned real estate executive Ciere Boatright as his commissioner of Planning and Development.

Johnson’s choice of Larry Snelling as his police superintendent has also played to rave reviews. Snelling was the obvious choice. He has a commanding and reassuring presence and has already won the support of the demoralized rank and file.

The mayor temporarily enhanced that good will by extending the police contract and sweetening police raises. But the feel-good period was somewhat short-lived.

He infuriated officers by twice asking City Council members to reject an arbitrator’s ruling that would have allowed police officers accused of the most serious wrongdoing to bypass the Police Board and take their cases to arbitration. The second time around, the vote was 32-18.

As expected, a judge sided with the police union, but agreed to make the arbitration process more public. That made the back-to-back City Council votes more than “symbolic,” Johnson said.

“For a Democratic mayor to be so anti-union it’s pretty breathtaking,” said Fraternal Order of Police President John Catanzara.

Johnson did keep a campaign promise to hire 200 new detectives and to free officers for street duty by hiring civilians to perform office jobs. And to the consternation of some progressive allies, he increased the police budget to nearly $1.99 billion.

But Snelling told a town hall in Jefferson Park recently that Chicago is still down about 2,000 officers citywide and struggling with low recruitment.

Like Lightfoot, Johnson has devised a plan to get at the root causes of crime.

His version takes a hyperlocal approach, focusing on 10 multi-block areas in four neighborhoods: Englewood, Austin, Little Village and West Garfield Park.

Those neighborhoods — plagued by school closings, high dropout rates, and a lack of public amenities like parks and libraries — will receive an array of services, including priority in another round of the city’s guaranteed minimum income program.

Johnson has also put a heavy focus on creating more summer jobs and neighborhood recreational opportunities for young people to give them alternatives to an ongoing trend of mass gatherings that have turned violent downtown.

Shootings and homicides are down slightly, but robberies remain stubbornly high. In neighborhoods across the city, many Chicagoans continue to feel unsafe, waking up to reports of another wave of strong-armed robberies, store break-ins and carjackings.

Reducing violent crime remains such a priority, alderpersons who believe ShotSpotter is an effective prevention tool are vowing to, perhaps symbolically, defy the mayor and tie his hands when it comes to ending the contract.

Johnson plays City Council tie-breaker

Twice in the first year, Johnson has been forced to cast the tie-breaking City Council vote: once to save his now-ousted Zoning Chair and floor leader, Ald. Carlos Ramirez-Rosa (35th) from censure, and the second time to deliver the deciding vote on a non-binding resolution for a cease-fire in the war between Israel and Hamas in Gaza.

The cease-fire resolution strained the mayor’s relationship with many Jewish leaders and the council’s only Jewish alderperson, Debra Silverstein. The lingering anger led some prominent Jewish elected officials and civic leaders — including the Anti-Defamation League Midwest, State Sen. Sara Feigenholtz and State Rep. Bob Morgan — to decline the mayor’s invitation to a recent meeting meant to ease the tension.

But had he not supported the cease-fire resolution, Johnson would have diminished his relationships with progressives and Arab Americans. He noted calling for a cease-fire is in line with his values and that several progressive, pro-Palestinian Jewish groups did attend the meeting.

“As far as me calling for peace, I hardly consider that controversial. The entire country and people around the world are calling for that. That’s something that we value as residents of the city of Chicago, but it’s also part of our responsibility as global residents that calling for peace and an end to war is a part of our very profound tradition,” he said.

The Chicago area’s large Palestinian community demanded that Johnson and his City Council majority take a stand. They waited for months for him to do it, and made their feelings known, attending numerous raucous City Council meetings.

The division caused by the war has now spread to college campuses in Chicago and nationwide. It foreshadows the civil disobedience that might come to Chicago when Democrats gather in August to formally nominate Joe Biden for reelection.

If Johnson is too timid, he risks allowing demonstrators to run roughshod over Chicago. If he allows Chicago police to be too heavy-handed, he runs the risk of civil rights violations and the inevitable comparison to the disaster of the 1968 Democratic National Convention in Chicago.

Chief of Staff Rich Guidice, a seasoned City Hall lifer, was widely expected to remain on the job through the convention with the expertise garnered from having guided Chicago through every major event in decades. But Guidice abruptly resigned last month.

He was replaced by former State Sen. Cristina Pacione-Zayas, a proven progressive who has been at the forefront of Johnson’s migrant crisis strategy.

The tie-breaking vote that spared Ramirez-Rosa from censure followed his resignation after apologizing for bullying and threatening colleagues to block a symbolic referendum that would have allowed voters to weigh in on whether Chicago should remain a sanctuary city. Johnson was determined to stop it and Ramirez-Rosa helped him do that.

Johnson has yet to name a replacement for Ramirez-Rosa — either as Zoning chair or floor leader. Some council members are demanding that Ramirez-Rosa be replaced by a member of the Latino caucus, but Johnson has yet to find someone he trusts who can also win the support of the council.

Meanwhile, some of Johnson’s own progressive supporters feel forcing Ramirez-Rosa’s resignation was hasty, went too far and that an apology should have sufficed.

Backing Bears puzzles progressives

Progressives were also left scratching their heads when Johnson embraced the Bears’ plan for a sprawling lakefront stadium south of Soldier Field that relies on billions of dollars in state and federal funding that has neither been approved nor identified.

When the Bears unveiled their stadium plan, Johnson acted more like a cheerleader than a guardian of taxpayers and protector of precious lakefront parkland.

When asked if the plan violated the city ordinance prohibiting new construction along the lakefront, Johnson referred to the Bears’ promise of increased green space on the Museum Campus.

He failed to mention that those additional 14 acres would come only if the state and federal governments can come up with all $1.5 billion needed for the infrastructure improvements.

Putting the Bears stadium near the top of his legislative wish list contradicts the stand he took on the issue during the campaign.

But Johnson argued that Soldier Field is a “100-year old building” that was rebuilt in 2003 with a ballooning debt that will drain city coffers unless the outstanding bonds are refinanced as part of the new stadium package.

“If someone else has another solution that addresses this problem, then they should put that on the table,” Johnson said.

Every mayor loves a giant public works project that generates jobs, contracts and political donations and serves as a feel-good diversion from Chicago’s intransigent problems. That’s what the failed 2016 Olympics bid was to then-Mayor Richard M. Daley. Former Mayor Rahm Emanuel had a similar diversion with Elon Musk’s subterranean, high-speed tunnel train to O’Hare Airport.

Johnson’s stadium plan appears to be going nowhere. Springfield has far higher priorities than to shell out billions to the Bears.

“The position he’s taking there… seems to run at odds with his key base of support from progressives. I understand the temptation and desire to put forward a signature project, a legacy project if you will…But, it just seems like an unforced error in the way he rolled it out,” said David Greising, president and CEO of the Better Government Association.

“Unforced errors is sort of a common theme that we are seeing in many respects … Communication with the public and the press remains lacking. And even at a moment like the Bears press conference where he’s speaking in platitudes from scripted remarks and can’t really engage with the questions being asked is undermining his ability to earn support from people most affected by the decisions he is making.”

Pritzker did not address the Bears stadium controversy or other points of tension with Johnson. He said instead: “The first year of any administration is often the most challenging and I commend Mayor Johnson and his team for reaching this milestone.”

Springfield stumbles

A stadium defeat would not be Johnson’s first in Springfield.

Last month, the Illinois House took an overwhelming vote to curb the power of Johnson’s hand-picked and revamped school board. A Senate committee did the same this week during Johnson’s first Springfield lobbying trip as mayor. The bill would prevent Chicago Public Schools from making any admissions or funding changes to selective-enrollment programs and closing any schools until a fully elected school board takes control in early 2027.

The House vote was 92 to 8. There was no mistaking the message to Johnson’s board, which wants to prioritize investing in neighborhood schools over choice schools like selective enrollments, and his allies in the Chicago Teachers Union. The original bill was amended to extend an existing moratorium on closing all schools, and not just selective schools, after lobbying by the teachers union.

Asked what message he took from the vote to tie his hands on an important education issue, Johnson focused on the fact that there has been no final vote.

“It’s not a law, so nothing has happened,” he said.

An emotional CTU President Stacy Davis Gates — perhaps reflecting on setbacks like these — told supporters last fall she was “ashamed of myself” for having put “my brother,” Johnson, in “an impossible place.”

Asked recently what she was ashamed of, Davis Gates talked about the resistance that Johnson has faced during his first year in office.

“Transformation is happening right now in Chicago and every corner of the city because of his leadership. And that level of transformation either makes you a hero or it makes you a villain,” Davis Gates said. “It’s not lukewarm. It’s either hot or cold and that is a very precarious position to live in.”

As a candidate, Johnson promised to make progressive changes to Chicago Public Schools, and he has.

His revamped board is led by former science teacher Jianan Shi, who also led the parent advocacy group Raise Your Hand for Illinois Public Education. Johnson’s board is filled with others with community organizing experience.

That board has delivered on a promise to shift away from student-based budgeting that progressives argue exacerbates challenges at schools serving low-income communities, and toward a need-based funding model.

But he’s already disappointed some parents by sticking with a plan for a phased-an elected school board instead of delivering that pivotal reform in one fell swoop.

Johnson will also have to find a way to deliver for the schools, parents and his former colleagues at the teachers union without breaking the bank in the CTU contract he is now negotiating. Teachers started out by demanding a 9% raise, or to match inflation, whichever is higher.

“I know what it takes–from a teacher’s perspective, as well as a parent’s perspective, and a student’s perspective–to have a more transformational educational experience,” Johnson said. “And that’s what our focus has to be: funding our schools and actually transforming them so that they are fully, fully expressed in an equitable way.”

Chicago Public Schools is staring at a $391 million deficit for the upcoming school year, which doesn’t account for raises currently being negotiated for teachers and a 4% raise that has already been promised to support staff. The CTA and other mass transit agencies are facing their own funding cliffs.

That’s yet another point of contention between Johnson and Pritzker.

The governor is among those demanding a leadership change at CTA before any new money is provided. Others want to merge all four Chicago area mass transit agencies into a single super-agency to reduce costs, improve operations and create a unified fare structure.

Johnson has stuck with embattled CTA President Dorval Carter Jr., no favorite among Chicago alderpersons, even though he was harshly critical of the CTA’s performance during the campaign.

When Pritzker dared to demand a leadership change, the mayor replied that he alone gets to choose the CTA president, adding “If people want to be mayor they should run for it.”

Johnson likes to say he intends to serve for the 23 years he would need to become Chicago’s longest-serving mayor, bypassing Richard M. Daley.

But that will require him to grow and mature in the job and survive many upcoming tests. While his first budget made no real political waves, the second will demand that he either make cuts, raise property taxes or raise new sources of revenue while continuing to chip away at his commitment to invest in people.

Despite Johnson’s recent olive branches to the business community, Greising said many of the business leaders he talks to “feel like they still don’t know him, still don’t understand what he’s trying to do and what they can do for him and still don’t feel heard by him.”

“Every successful mayor has found a way to have the business community with him. And this mayor, so far, doesn’t seem to work very hard on that. He hasn’t…cracked the code yet,” Greising said.

“We shouldn’t be all that surprised when we elect someone with his background that there’s a very steep learning curve. But…he really needs to invest his effort into growing in those areas where he is falling short. If he doesn’t do that with urgency, then it will be too late.”

Davis Gates acknowledged the growing pains.

“Our entire movement has to get comfortable with having an opportunity to win. For so long in this city, people who have needed [the most] have been told ‘no.’ We are all undergoing a transformation of going from demanding a thing happens, fighting for a thing to happen, protesting, rallying, door knocking, to going into a legislative experience,” she said.

“To make things happen, those are different muscles. We used all of our strong muscles to get to this point. The muscles that we have to develop now – not just as a movement, not just as a mayor, but as an entire city – is number one we’ve got to get more inclusive. We’ve got to figure out how to work past our differences.”

Johnson acknowledged that it will take some time for this “new formation that we have in Chicago” to settle in.

“Let’s just be honest here. The way these systems have been built, particularly government, they have been built in a very complex way to favor the few,” he said.

“There has been sort of an unfettered access of a handful of powerful people having access to the fifth floor … Maybe they’re not used to sharing. And that’s going to take them some adjustment.”

Fran Spielman covers City Hall for the Sun-Times. Mariah Woelfel and Tessa Weinberg cover city government and politics for WBEZ.