Progressives need to reckon with Brandon Johnson

The story of an uncompromising mayor who ignored trade-offs

Two years ago, Brandon Johnson was elected mayor after pledging to bring a “bold progressive movement” to Chicago. But today, the leader of America’s third-largest city has an approval rating of 14% and the unofficial title of “least popular politician in America.”

The story of the teacher union organizer turned failed big-city mayor is easy headline fodder for a right-wing publication like the National Review. But the progressive outlets that once enthusiastically applauded Johnson’s rise have been conspicuously silent on the factors that have led to his downfall. What’s missing is a more rigorous assessment of Johnson’s tenure — one that doesn’t end with the conservative conclusion that all Democratic mayors are doomed to fail, or ignore the fact that Brandon Johnson’s brand of urban governance has clearly not resonated with the people of Chicago.

Here’s the question at the heart of this story: Does Johnson’s shockingly low approval rating stem from a combination of incompetence and problems beyond his control, or does it point to a larger problem within the political coalition that brought him to power? Chicago has seen progressive mayors before, but never one so directly shaped by the powerful Chicago Teachers’ Union and the constellation of organizations that dominate the city’s left-wing politics.

Brandon Johnson’s tenure deserves close attention—not just because it highlights Chicago’s problems, but because it sheds light on a broader debate about progressive governance in cities. Candidates like Zohran Mamdani in New York are running on similar platforms with similar political coalitions. Progressives backing these campaigns should take a hard look at why Johnson’s agenda hasn’t worked in Chicago—a city struggling with persistent crime, steady population loss, and a tax base that's already among the most heavily burdened in the country.

A misguided mandate

Brandon Johnson’s first mistake was misreading the political environment that brought him to power. In 2023, Chicago voters were primarily concerned with the COVID-era crime spike and the rising cost of living. In fact, they were so concerned that they nearly elected Paul Vallas, a conservative Democrat who ran a campaign laser-focused on those issues. But Vallas was weighed down by his history of failed runs for elected office and his controversial tenure as CEO of Chicago Public Schools.

Full disclosure: I worked for a communications firm that assisted Vallas’s campaign, so I’m confident when I say that Vallas’s biggest vulnerability wasn’t entirely on the issues, but rather his reputation as a disloyal Democrat. He had previously described himself as “more of a Republican than a Democrat” and criticized Barack Obama on conservative talk radio.

Even though many Chicago voters were receptive to Vallas’s moderate messaging, Johnson defeated him with a coalition of Black voters from the South and West sides, along with white liberal voters from the North. This victory came with two major caveats: the margin was the narrowest in recent city history and turnout barely cracked a third of registered voters. Historically, low-turnout elections disproportionately favor more extreme candidates, so the result was certainly not a sweeping mandate. ¹

That didn’t stop Johnson from claiming support for his agenda from “The Soul of Chicago.” This meant redirecting funding away from the police department, ending charter school expansion, providing a favorable contract to the Teachers’ Union (of which he was a member), and expanding social services with steep tax increases.

But the reality in Chicago pointed to a different governing agenda. The city had nearly exhausted its COVID stimulus funds and was staring down a mounting budget deficit, worsened by population loss from remote work and a looming pension crisis. Crime, though on the decline, remained above pre-pandemic levels and was still the city’s top concern. Even well-intentioned proposals—like increasing funding for affordable housing construction—needed to be considered under these very real constraints.

In other words, Johnson needed to make some serious budgetary trade-offs. Especially because the looming migrant crisis was layering another massive strain on the city’s financial resources.

Mismanaging the migrant crisis

The city aldermen and political observers I spoke with mostly pointed to the migrant crisis as the single biggest driver of Johnson’s unpopularity. To be fair, the problem began under his predecessor and would have challenged any mayor. But no one I spoke to said Johnson handled it well.

In large part, that’s because Johnson’s background as a teachers’ union organizer and brief stint as a Cook County Commissioner didn’t prepare him to handle the bureaucratic nightmare of settling 40,000 migrants across the city. Alderman Raymond Lopez, a moderate from the West Side, told me he never expects a mayor to come into office with a complete command of city management, but Johnson fared worse because he and his staff largely came from a similar activist background.

That helped lead to missteps like wasting millions to build winterized tents on land that was known to be contaminated, and allowing out-of-state contractors to charge exorbitant fees for shelter staff that ranged up to $200 per hour. Governor Pritzker criticized Johnson for not coordinating with the state to open new shelters quickly enough. Eventually, the scarce shelter space overcrowded, migrants began to face evictions, and homelessness in the city nearly tripled.

The predominantly Black South Side neighborhoods that were promised more city investment by Johnson also bore the brunt of the migrant settlement activity. When tens of millions of dollars suddenly become available to assist newly settled migrants, frustration began to mount. After the City Council voted for a $70 million migrant aid package, progressive Alderman Desmond Yancy summarized these tensions best, noting that, “When Black residents see the large financial investment being made to help support the migrants, they rightfully question when it will happen for them.” Alderman Lopez told me the Latino community expressed similar resentment, largely over the sense that Johnson prioritized the needs of newly arrived migrants over the undocumented DACA eligible Chicagoans who had worked in the city for years.

Ultimately, this was less a failure of ideology than one of management, and the problem would’ve proven challenging for any mayor. The more interesting question is how Johnson handled issues that were more within his control.

Brandon Johnson needs to consider trade-offs

The “Bring Chicago Home” (BCH) ballot initiative was Johnson’s signature campaign policy—and ultimately a signature failure of his mayoralty. The plan aimed to raise transfer taxes on all real estate transactions above $1 million, generating $100 million annually to fund homelessness services. Johnson branded it a “mansion tax” to redistribute wealth to underserved communities, but in practice, it would have operated as a punitive, one-time sales tax on any new business that needed to acquire property. And likely would have made it harder to construct new apartment buildings.

Consider Chicago’s core post-pandemic challenge. For decades, the city’s tax base relied heavily on its business district, but the rise of remote work hollowed out downtown, leaving empty offices and underutilized real estate. The BCH initiative would have discouraged the type of reinvestment necessary to revive all sorts of businesses, since $1 million is an incredibly small bar for a real estate transaction. But this was a longstanding progressive priority that dated back to the Lightfoot administration — she opposed — and Johnson had no interest in adjusting it to fit the city’s current economic situation.

The upside of BCH was simple: more money to support increased homeless services and affordable housing construction. However, Johnson never released a concrete spending plan, so there were worries the revenue would be misused by an administration with a reputation for poor fiscal management. When BCH was voted on as a ballot proposition, Chicago voters rejected it and Johnson’s own progressive allies cited this exact reason for its failure.

In the years since, Johnson hasn’t done much to ease those concerns. He pledged $1.5 billion in taxpayer money to help fund a new Chicago Bears stadium — even while the city still owed $600 million for renovations to the old one. And during his first two budget negotiations, he refused to cut city services or trim city employee headcount — even after the city’s debt was downgraded due to a “structural budgetary imbalance.” Johnson recently assembled a budget working group to help manage the deficit, largely as a response to Trump’s threat to withhold federal funding to the city. But half the invited aldermen refused to participate, dismissing the group as “more symbolic than productive.”

Conor Durkin, who writes an excellent newsletter on Chicago urban policy, told me that it is time for Johnson to start making some tough budgetary choices. And with discretionary spending and city staffing levels significantly higher in the post-COVID era, large parts of city government are ripe for reform.

Here’s a small example Durkin offered: The employees in the city tree maintenance department has increased in size by 50% over the past decade, but over the past two years, a new process that regularly deploys maintenance on a block by block basis, rather than individually responding to constituent calls, has improved efficiency in the department by 118%. Does Johnson have any desire to trim back on the tree maintenance budget, or is even something that low-hanging off the table?

Here’s a bigger example: The average home in Chicago sells for about $350,000. But the city spends almost $750,000 per unit on building new affordable housing projects — while Houston, the next largest city in the country, spends $328,000 per unit. Durkin says that this is largely because building cost is not a major emphasis in how the city evaluates construction projects. The formal proposal process only weights 3% to “cost containment,” while categories like “the makeup of the development team” and “energy efficiency” are 15% and 13% respectively. If costs were 30-40% of the score, Durkin says, developers would have a real incentive to design around them.

Brandon Johnson believes that the “68,000 people who are unhoused deserve a champion,” and he’s absolutely right; homelessness is a moral stain on the city. But being a champion for the unhoused isn’t just about demanding more taxpayer money to support them; it’s also about making the tough decisions that will build more affordable housing on the cheap, along with an approach to government spending that inspires the confidence of his voters to entrust the government with their tax dollars.

Who has the mayor’s ear?

Another important way to understand the downfall of Johnson is to understand his relationship with the Chicago Teachers’ Union. Polling on the CTU is pretty sparse, but a recent survey has its net favorable rating at negative 31 and the head of the union, Stacy Davis, at negative 37. In school board elections last year, six of the nine candidates who won elections were not endorsed by the union.

During the campaign, Johnson was described as the “Teachers’ Union candidate,” since he was literally still a member. He’s now formally on leave from the union, but he’s still considered the CTU mayor.

Negotiating contracts between the union and the mayor are normally contentious, with the union pushing for fiscally untenable demands, the mayor rejecting them, and everyone eventually meeting somewhere in between. But during the lead-up to contract negotiations, Johnson immediately acquiesced to the union’s primary demands and urged the Chicago Public School CEO to take out a high-interest loan to partially cover the $4 billion budget deficit that the contract would have caused. The CEO refused, so Johnson demanded he step down. The entire school board resigned in protest, and Johnson appointed new board members to remove him. Some of his own progressive allies called the decision “dictatorial.” Johnson compared those who questioned the legitimacy of some of the union demands to members of the Confederacy who opposed the abolition of slavery.

It didn’t have to be this way.

There’s a movement inside the Teachers’ Union to unseat the leadership for focusing too much on politics —only 20% of the union’s spending goes to member representation, and they regularly spend millions each year supporting unrelated political causes. But it’s anathema to Johnson’s own politics to support such reform. He and the current leader emerged from the same faction within the union, a group that, according to the left-wing magazine In These Times, began as “a study group reading The Shock Doctrine and applying Naomi Klein’s critique of neoliberalism to Chicago’s politics and education policy.”

Understanding Johnson as an organizer steeped in the dogma of left-wing Chicago groups in the city, rather than an elected official who merely seeks their endorsement, is the best way to understand why Johnson has been so uncompromising. David Greising, the CEO of the nonpartisan Better Government Association, told me that Johnson never understood the “difference between standing one’s ground based on principles and having a feel for the trades that need to be made in order to effectively make progress toward those goals.”

To be fair, Johnson hasn’t gone all-in on the left’s public safety agenda—he appointed a well-regarded police superintendent, and crime is falling. But he also overrode the City Council to cancel the city’s gunshot detection program (evidence on its effectiveness is mixed, but some aldermen in high-use neighborhoods supported keeping it). And has done little to address the city’s shortage of detectives.

Two-thirds of Chicagoans disapprove of Johnson’s handling of public safety and crime remains the number one issue in the city. So more clearly needs to be done to prioritize this issue, even if it means alienating some of the left-wing groups that helped elect him.

Big-city progressives need to reflect

At the federal level, there are strong progressive arguments for an agenda that centers around making the wealthy pay their fair share, reining in corporate abuse, and expanding the social safety net.

But the tax and spend playbook can’t be exclusively deployed to solve the problems in Chicago. Raising taxes on an already tax-burdened population risks further depopulation. The city’s credit rating was just downgraded for the first time in a decade. And unlike Phoenix or Miami, Chicago can’t rely on the lure of reliable sunshine to attract new residents.

That means progressives need to consider how they can grow their tax base in a constrained fiscal environment. And that starts with reflecting on the questions that Brandon Johnson has been unable to solve.

How can Chicago build affordable housing more efficiently to reduce homelessness? How can the city add housing supply in its highest-demand neighborhoods to increase population growth? Can the teachers’ union temper its budget demands and embrace higher standards to improve student outcomes? Which policing investments will reduce homicide rates while building community trust?

These aren't just Chicago questions—to some extent, every major blue city faces them. New York can afford to ignore them longer, thanks to stronger population demand, but even there, neglect comes at a cost. Across the country, urban voters are drifting rightward, and lower-tax cities in red states are growing faster. The urban-left coalition can't afford to ignore these realities.

And the broader progressive network that rallied behind Brandon Johnson in 2023 needs to reckon honestly with why his mayoralty has failed the people of Chicago.

1. Chicago hold it’s mayoral election in February of off-cycle years with a run-off in April. Barely anyone realizes it’s happening!