Michael Dwyer / AP Photo

Which Way Mamdani?

Ben Krauss

November 05, 2025

Chicago’s Brandon Johnson and Boston’s Michelle Wu are progressive mayors with very different approaches. Whose lead will Mamdani follow?

Chicago’s Brandon Johnson and Boston’s Michelle Wu are progressive mayors with very different approaches. Whose lead will Mamdani follow?

There’s one mayor that Zohran Mamdani doesn’t want to be compared to: the last left-wing activist who took charge of a major American city.

In 2023, Brandon Johnson ran for mayor of Chicago on an ambitious agenda that included increasing city spending, reducing the power of the Police Department and raising taxes on the wealthy. When he unexpectedly defeated his moderate opponent, his victory resonated nationally as a triumph for the urban left: A former teachers’ union organizer, schooled by Chicago’s activist class, had taken control of America’s third-largest city.

It’s obvious why Johnson is compared to Mamdani. But to anyone who follows Chicago politics, it’s clear why the people making the comparison tend to be Mamdani’s critics rather than his allies. That’s because Johnson’s tenure has been, by nearly every measure, a disaster. The migrant crisis undermined his administration from the start, but his mismanagement of it fueled public distrust and helped sink key spending priorities. Chicago is not the dystopian city of President Donald Trump’s imagination. By many measures, crime is falling, and the population is starting to rise. But Johnson’s unwillingness to reform spending has led to the most severe urban debt crisis in the country. It’d be one thing if current levels of government largesse produced top-notch city services. Unfortunately, few believe the city delivers competently on core responsibilities like transportation infrastructure or affordable housing, and half of city voters list taxes as a top concern. The result is a Johnson approval rating that sits between 14% and 25%.

If Johnson represents the future that critics fear Mamdani will bring to New York, Boston’s Michelle Wu offers a more hopeful analogue. The former city councilor was elected in 2021 and is often grouped with Johnson as a part of the “progressive takeover of big cities.” She ran on a platform that will sound familiar to Mamdani fans: fare-free transit, rent control and climate action.

Importantly, while Wu is more left-leaning than her predecessor, she has a more varied ideological history than Johnson. When she ran for City Council, one of her top priorities was cutting red tape for businesses, and her first vote in office was for a moderate Council president. As mayor, Wu scaled back some ambitious proposals on transit and policing, prompting criticism from the left that she abandoned her campaign promise for transformative change.

Wu can still point to victories on green infrastructure investment in schools and a major spending boost for universal pre-K, but those left critics have a point. In polling and a recent interview series by The Boston Globe, most residents say they haven’t seen much change in the city, aside from less crime and more expensive rent. The good news for Wu is that it isn’t much of a problem; she just cruised to reelection, running unopposed after opponents failed to galvanize sufficient support. It turns out that pragmatically picking the right political fights and avoiding allegations of mismanagement was enough. The residents of Boston weren’t clamoring for sweeping change.

City-to-city comparisons are difficult. Chicago is well over three times the size of Boston, and New York City is nearly three times the size of Chicago. The powers of the mayoralties vary substantially. And all three cities perform differently on key issues like education, crime and economic growth. Still, New York’s new mayor can take cues from Wu’s successes and Johnson’s governing failures.

Promises and pragmatism

Mamdani can start by avoiding Johnson’s excessive deference to the demands made by certain unions and single-issue organizations that dominate the city’s left-wing political coalition.

Take education, for example. Chicago’s public schools face rapidly declining enrollment and rising per-student costs. Reform has been a decades-long challenge for leaders across the political spectrum, but Johnson worsened the situation by deferring to the deeply unpopular and overtly political Chicago Teachers’ Union, where he once held membership. It may have been unsurprising, but was nevertheless disappointing when Johnson declined to push for the closure of severely underenrolled schools while supporting additional funding to expand the expensive and often underperforming “Sustainable Community Schools” program. The situation turned scandalous when the school system’s CEO refused a $300 million high-interest loan to cover the union’s new contract demands. Johnson ordered the school board to fire him; he resigned in protest, and Johnson proceeded to appoint a board of union-friendly allies. Meanwhile, the structural problems in the school system remain unaddressed.

Having steady working relationships with the public and private sector unions is foundational to any successful mayorship. But, as David Greising of Chicago’s nonpartisan Better Government Association told me, 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.” While that tension was clearest with the teachers’ union, it extended to other realms — such as when Johnson refused to lay off any municipal workers despite the city badly needing to cut back on its financially unsustainable staff levels.

Wu handled these trade-offs much more intelligently. Tensions ran hot with Boston’s teachers’ union during contract negotiations, but she was able to deliver fair wage increases without yielding to less reasonable demands. Municipal workers pushed for increased pension payouts, but Wu wisely rejected them for being financially untenable. The police union — a typically less friendly interest group for progressive mayors — even agreed to major reforms in its disciplinary system.

As Wu put it herself, “We may not always agree on the positions that are taken, or the outcomes that will come from certain changes that are being suggested, but we can all agree on wanting to do our best by the residents of Boston and by our workforce.”

That’s a good reference point for Mamdani. Supporting working-class New Yorkers should mean siding with unions when they’re right on policy or making certain pragmatic concessions to keep City services operating — but saying a firm “no” to demands that unnecessarily drive up costs and undermine good governance. For instance, Mamdani plans to build 200,000 units of affordable housing at the somewhat low cost of $500,000 per unit. But building with only union labor, as Mamdani plans to do, yields a typical cost of $800,000 per affordable housing unit. If affordability is truly his north star, will some demands from organized labor give way for the greater good?

The economist Mancur Olson coined the term “stationary bandits” to describe how roving warriors settled in early farming communities, extracting goods while maintaining certain basic government services. The writer Matt Yglesias applies the same logic to some organizations in New York City, which serve important functions in the city but advocate for certain policies that extract costs from the City.

While Mamdani has generally suggested that labor and the general public aren’t in tension, in point of fact they are — in ways a smart progressive needs to address.

For another example, think of the transit union’s costly attempt to prohibit one-person train operation, a standard policy in metros around the world. The onerous crane regulations that increase construction costs while protecting entrenched construction interests. Or the recent City Council plan to make New York virtually the only city in the country to mandate gas-powered appliances installation by master plumbers — a policy that will increase costs for landlords, and consequently renters. Is this the kind of thing an affordability-obsessed mayor will bless or resist?

Mamdani has the opportunity to stand against such banditry because, unlike politicians like Johnson or Cuomo, he doesn’t owe his rise to these organizations’ endorsements or fundraising. His support came authentically from New Yorkers who were sick of living in a city that feels so unaffordable. But time will tell which path he chooses.

He’ll need to show similar flexibility in other areas where his stated principles and pragmatism clash.

The city’s largest-in-the-nation public school system has middling test scores and the highest per-pupil spending just about anywhere. Mamdani has said he wants to better serve parents and students, especially low-income parents and students ill served by the current system. But if he sticks to some of his more rigid campaign pronouncements, that’ll be difficult. He’s positioned himself as a foe of many charter schools, which serve precisely this population. He’s telegraphed resistance toward merging or closing poorly performing, underenrolled schools. And he’s said he’s against mayoral control of the schools in its current form, a stance that’ll make it very hard to go “line by line at every single position” in the Education Department bureaucracy to ensure that they are “actually working towards the betterment of the system.”

It’s not just unions he needs to be prepared to disappoint — it’s his uber-progressive allies with the Democratic Socialists of America. The left political organization has been pragmatic during the campaign, refusing to denounce Mamdani when he backed the construction of new jails and apologized for his past criticisms of the NYPD. Their bet is that moderation will be worth it when Mamdani makes good on certain long-standing DSA priorities.

But what happens when Mamdani isn’t able to get the State approval he needs to fund the free bus program? Or, if his City-run grocery isn’t able to expand and feed low-income residents at scale? Mamdani will need to think critically about which priorities can most cost-effectively improve life in the city, even if it means disappointing his long-standing ideological allies.

Taxing and spending

So much of this comes back to budgets. Like every other major city in the country, New York City is facing a looming budget deficit that’s exacerbated by impending cuts in federal assistance from a hostile Trump administration. One of Mamdani’s biggest responsibilities in the coming years will be navigating that situation responsibly.

Michelle Wu has addressed Boston’s budgetary problems with targeted cuts and emphasized, “We're holding steady and ensuring that we’re doing things in a really disciplined and fiscally conservative way.” She also dialed back some expensive campaign promises like free transit. Chicago, meanwhile, faces a far deeper budget crisis that began before Johnson even took office. The nonpartisan Civic Federation and other seasoned budget watchdogs have urged Johnson to rein in spending before turning to new taxes. But the mayor has largely brushed aside that advice, sticking to his refrain that wealthy Chicagoans need to “put more skin in the game.”

It’s hard for Johnson to get beyond taxing and spending because he shares Mamdani’s belief that the biggest challenge in municipal government is rampant fiscal austerity paired with a supposed tendency to let the rich get away without paying their fair share. The truth is that both Chicago and New York City are the capitals of states with some of the highest combined state and local spending per capita, and government expenditures have increased by 20% in New York City and 58% in Chicago since 2020. Residents in New York City face among the highest combined income tax rates in the nation.

That doesn’t mean Mamdani shouldn’t seek to increase spending on certain vital services or pursue tax increases to fund that spending, but he should learn from Johnson’s inability to rein in costs in the city.

Johnson’s affordable housing policy offers a useful example. While it’s not the biggest cost in either city’s budget, it is an area where Mamdani also wants to increase spending. Johnson recently pushed for a $1.25 billion loan to support new construction. But he’s expressed no interest in reforming a system that spends almost $750,000 to build a unit of affordable housing — Houston, the next largest city in the country, spends $358,000. His latest affordable housing policy is loaded with more onerous design requirements that will make it worse.

Michelle Wu has increased affordable housing spending too, and Boston has seen its highest affordable housing production since the 1990s. Still, construction costs remain high, and overall housing production in the city has fallen. High interest rates and rising construction costs have undermined builders everywhere, but critics say Boston has been hit harder by new green energy codes and stricter inclusionary zoning rules. Both Wu and Johnson have implemented some other good supply-side reforms, like reforming parking mandates. Neither are models for unleashing a housing boom.

Albany is almost certain to reject raising the debt limit to let New York City borrow the $70 billion Mamdani wants so that the public sector can build affordable housing. If he insists on this approach, he risks looking naive about fiscal constraints — the same political liability that has repeatedly undermined Brandon Johnson. Mamdani can still increase spending on affordable housing construction, but he should reform the complex design requirements that are needed to build. Sean Campion, the director of housing and economic development studies at the Citizens Budget Commission, points to these regulations as a key reason why affordable housing construction is so expensive.

Much has been written about the impracticality of Mamdani’s rent-freeze plan. Less covered is Mamdani’s misguided desire to enhance the current affordability standards under the 485-x tax credit and zoning for Mandatory Inclusionary Housing (MIH). The tax credit functions as a carrot, cutting taxes for developers that include affordable housing, while MIH makes additional density contingent on providing a certain percentage of affordable units. Importantly, Alex Armlovich, a housing analyst at the Niskanen Center, told me both requirements “are already among the strictest in the country and that all the city needs is more upzoning to scale them.” Mamdani has talked a big game when it comes to increasing housing supply. Now, he needs to change his policies to match his rhetoric.

Nuts-and-bolts

Regardless of whether Mamdani pursues the wisest housing policy or tackles extractive special interest groups, the biggest thing that will determine his fate in his first few years is competency. Will New Yorkers see their city getting and feeling safer? Will they sense the very basic mechanics of government working better?

Listening to Mamdani’s rhetoric, he seems to understand that this is how he’ll be judged. But understanding the importance of good governance and actually governing well are two very different things.

Some Bostonians criticize Michelle Wu’s policy positions, while few argue that she has been incompetent. Ford Cavallari, chairman of Boston’s Alliance of Downtown Civic Organizations, describes Wu as someone who “ran as an outsider-slash-reformer” and “ended up governing as an insider.” This is the result of a few factors: Wu’s long history of political pragmatism, background in business and private consulting and — arguably most importantly — good staff.

On the other hand, even Johnson’s progressive allies admit that he struggled to staff his administration with the kind of experienced managers the City requires. As one put it, the mayor “involved so many people who wanted to feel like they had a seat at the table.” That instinct to appease so many loyal factions left his government stretched thin on expertise — contributing to the administration’s faltering response to the migrant crisis and to a series of avoidable political setbacks. More than any of his aforementioned policy failures, it was this sense of chaos and mismanagement inside the administration that drove Johnson’s approval so low.

To be fair, Johnson has still been able to achieve progressive victories like ending the subminimum wage for tipped workers and mandating 10 days of paid leave across the city. The left-wing political strategist Waleed Shahid believes these achievements were undermined “by a sophisticated opposition network that dictated the political narrative.” Perhaps, but actual results have mattered mightily too.

Wu entered office with a far less entrenched political opposition and, in turn, faced much less negative media. Mamdani will face a more organized and better-funded opposition that is much more similar to Johnson. They will be searching for mistakes, and Mamdani needs to avoid them by not hiring too many of the ideological and inexperienced staffers he’s carried on his campaign. Instead, he should follow the example of Bloomberg and even de Blasio by appointing seasoned staff and deputy mayors who command broad respect in their fields. This could mean the administration narrows its ambition to issues like rent control or free buses. But it will result in a more competently run City.

Mamdani’s opponents have spent the past year fearmongering about the possible nightmare of a socialist-led city. Mamdani’s political identity doesn’t mean he’ll manage the city poorly. In fact, as the 20th century “sewer socialists” in Milwaukee and elsewhere show, socialist mayors can preside over a growing city and establish great public works. Mamdani’s fate, and that of New York City, hinges less on ideology and more on effective governance that recognizes the need to make trade-offs. Brandon Johnson shows the danger of ignoring such governing complexities, and Michelle Wu is proof that progressives can narrow their governing agenda and remain broadly popular. Millions of New Yorkers voted for a better-functioning and more affordable city. If he’s willing to make some tough choices, Mamdani can deliver on that promise.