Congratulations! You’ve ascended to the third highest executive office in the American political system — mayor of a city. You’ve joined the ranks of such American luminaries as Harold Washington, Fiorello La Guardia, Bernie Sanders, Rudolph Giuliani, and Diamond Joe Quimby. You have at least four years of parade grand marshalling, police shootings, and construction signs with “[Your Name Here], Mayor” to look forward to. We hope this useful guide will make your stay in City Hall a comfortable and productive one. Below you will find some “Do’s and Don’ts” to help you on your journey.
DO: Understand What Exactly it is That Cities Can Do
Preemption
In the American political and legal system, cities are often referred to as “municipal corporations.” This is because cities are “incorporated” by state governments. They are subsidiaries, so to speak, of state governments. In the U.S., state governments are considered sovereigns, which means that they have all legal authority to do anything they want within their territorial borders, limited only by those things that the Constitution expressly prohibits, or assigns solely to Congress or the President.
Unless something is prohibited to it, the state government can do it. Your city? It’s another rung down. All your powers are derivative of your state’s. Like a parent on a 90s sitcom, your state brought your city into the world and it can take you out of it, too. Of course, if your city is big enough, it can do some big kid things: this is known in most places as “home rule authority.” Home rule authority means that your city government has the same power within its borders as the state has within its borders — unless the state has prohibited it to you. This is known as “preemption.”
So let’s take a couple random example cities: Chicago and New York City. Both are home rule cities in their respective states. But there are things that either the constitutions of those states or the specific state laws don’t let those cities do, and then things that Congress has preempted.
In New York for example, according to the courts anyway, NYC is prohibited from enacting a minimum wage higher than the state’s. In Illinois, Chicago is prohibited from imposing rent control.
And both cities have significant restrictions on how they can raise revenue. State law in Illinois limits how, and the type, of real estate taxes that Chicago can impose; in New York, the state law formulas for property taxes makes them de facto regressive.
Revenue
Hey, speaking of taxes, now that you’re a mayor, you will need to make sure you are taking steps to take care of your city’s condition. Please note that failure to invest in your city voids the warranty.
But you have a problem. Cities rely heavily on taxes that are beyond their control. Thirty-three percent of New York City’s budget, for example, comes from state and federal “categorical grants,” which means that the money has to be spent on specific things, and cannot just be ported around for your priorities. And while we hope for the best, we cannot guarantee that the federal government grants will be favorable. Or exist.
Another third of New York City’s budget relies on property taxes. Property taxes of course are keyed to home values — which means that gentrification boosts revenue. In 1994, the year Rudy Giuliani took office and New York’s gentrification turbocharged, the City collected about $7.5 billion in property taxes. In 2025 dollars, that would be about $17 billion. In 2024, the City collected $37 billion. The problem is that there is no practical way to increase property tax revenue in a progressive way without a serious change to state law — and even then, it will still likely impact many long-time homeowners whose home value is their nest egg.
The property tax thing is a big problem. Ultimately property taxes rise and fall based on the housing market, and thrive on the investment of real estate development capital. And real estate development capital is highly “sensitive” (their word; another word would be “extortionate”) to the “investment climate” in your city. That means that laws that protect the environment, require reinvestment, or protect workers, can provoke capital strikes or the threat of capital strikes, which can have immediate year-on-year impacts on your budget.
The next largest category of revenue is New York City’s individual income tax, which accounts for about 13% of revenues. The good news is that despite what rich people will tell you, rich people leaving your city does not have to hurt your income tax revenue, because if you find a way to raise everybody’s wages, then even if there is an exodus of your very highest earners (many of whom probably duck your taxes through address shenanigans anyway), it can be made up by incremental wage increases among your many, many residents.
The current reality of American cities is that structural reliance on federal grants creates a cycle of creating and then eliminating programs that erodes public trust in and understanding of government. From the point of view of the people, it seems arbitrary. Government services without predictability undercuts peoples’ belief in government, which in turn makes people skeptical about raising more revenue.
Cities have been put in a position where they need to be “entrepreneurial.” They need to entice investment. Would that that wasn’t true, but here we are. For the near future, that is just the reality. You have an opportunity now to seed some changes that could change that — a public bank, for example — but it’s your first term. You will need to make sure that investment is coming into the city — new construction, upkeep of buildings, employers. You need to preserve your tax base. Capital strikes and capital flight may be overstated, but it is real and it can hurt you.
You will need to be creative to identify ways to keep capital from fleeing (ideally in a way that advances your agenda and via rules and incentives that industries cannot resist) but does not structurally weaken your city’s services or harm your social base.
DON’T: Underestimate the Complexity of Your Bureaucracy
We are here to help you have the best mayor experience possible. So we encourage you to truly understand the complex machinery it takes to operate a city of several millions of people.
The Experts and Managers
In a city like Chicago, which is about one third the size of New York, there are about thirty executive departments and agencies, each of which needs to have a department head and likely at least a handful of additional key functionaries appointed to it. There are also at least a half dozen important boards and commissions with meaningful adjudicatory or policy-development roles. Now of course, many positions are mostly technical, so you can probably keep on the lifers: the Department of Water Management for example probably needs someone who knows how to get water in the city.
Many however are critically important to actually executing your vision for the city. In Chicago, of the 30-plus departments,at least half have some critical role to play in forming and implementing policy. You are, after all, an executive. It’s right there in the name! You need to execute. And every shortfall or mistake made by any of your departments is on you. So first of all you need competence: both in running the policy apparatus and managing the people. But you also need people who will think creatively and aggressively about how to shake things up and push the boundaries — which will inherently make enemies or at least opponents of those who are used to the way things work now. You didn’t become mayor, after all, to just be a steward for the status quo! The whole point of your campaign was a bold and imaginative vision for a city that would serve working people.
Let’s take a look at what we mean. Your Department of Planning. So critical! Just at the very tippity-top of this one department, in Chicago, are twelve appointed positions with important roles. These people not only have to implement your vision but they need to understand the entire field well enough to make the policy, too, to guide the careerists and fend off the lobbyists. They are the people who need to understand all of the different roles in the bureaucracy, understand how something gets from start to finish, so that when you have an idea, they can reduce it down to a series of operating rules that can become a law, and then be implemented. And you… You don’t even know what you don’t know! So when some lobbyist, or expert, or lawyer, comes to you and says, “Mayor, what you want to do is not possible because gahoxogan flurbiflu fleeb, without connecting the rambovoihaven to the shpu,” how will you be able to prove half of that was gibberish? Who can you turn to to push back on that conclusion — or confirm it?
A city like Chicago requires appointing at a minimum some forty to fifty key positions that need policy expertise, management and leadership ability, a nose for office politics — and a shared vision with you. And that is just for the executive departments. You will also need people to handle your intergovernmental affairs (your emissaries to city council, state and federal governments and agencies), plus the policy and communications team within your own office. That will approach well over a hundred people, each of whom represents you in every one of their dozens of daily interactions with other powerful people and the public. Every phone call to an important person they don’t return, every frustrated threat, every blown-off meeting, is yours to own.
Will you have your list on day one? Are you ready for boatloads of them to leave within a year or so?
New York City makes Chicago look like an adorable baby. According to the New York City open data portal, just since January 1, 2022, the New York Mayor’s Office has hired more than 100 still active people — excluding all interns, research project coordinators (almost all of whom make six figures), and everybody with an “assistant” designation. Thirty-three of those hires were for deputy mayors and director-level positions. These are just within the Office of the Mayor.
Even assuming you can get an average wins-above-replacement jobber for most of these positions — the various coordinators and such — you will still likely need at least a hundred or more people with subject-area expertise, management skills, political skills and vision, capable of representing you in complex and high-stakes discussions and negotiations 365 days a year.
Can’t the NGOs Just Do It?
We hear this all the time. I’m surrounded by policy experts! To my left and to my right are people with masters degrees in all sorts of things — food policy, public health, criminal justice, urban planning — who work at NGOs from whom policy papers flow like the mystical New York water that makes those bagels.
Indeed, you’ll have little choice but to turn to people from NGOs. That’s the truth. And not just advocacy NGOs who push policy on behalf of underserved communities, but also more traditional nonprofits that provide charity and services — community health clinics and the like. Why? Because you’re not going to go to some health care company executive for public health policy, or a business trade association for economic development advice. Duh.
But you do have to consider the drain. If you have potentially scores if not hundreds of positions to fill, will you really be able to cull those organizations of their best and brightest and expect them to stay around?
In Chicago, the mega-sized mayoral transition committee featured some 350 people. Of these, nearly 40% were manager-level and up figures from nonprofits. In a city with a total census of perhaps 3,500 staff in advocacy and advocacy/service nonprofits, that represents 5% of the total. Even if you choose to pull your people from the leadership and policy departments of unions and organizations like DSA, you will still be causing a very sudden and traumatic drain. In Chicago, there are approximately 700 full-time equivalent union staff and another 150 or so elected paid leaders of unions. The DSA chapter at times of high-participation campaigns has a couple dozen volunteer leaders. Decapitating these organizations of their policy experts, managers and leaders in one fell swoop is not particularly sustainable. It also represents a danger for you, because having weakened organizations on the outside means less support you can count on when you need to apply pressure to the system.
What’s more, there is a conflict to be considered, particularly in the use of directors from service/advocacy-blend NGOs that rely on city and state grants to conduct their work; that is, they have a material incentive to tailor policy solutions around outsourcing work to the NGOs they come from. But the NGO-ization of government services represents a privatization of the civil service — that is a symptom of the neoliberal privatization of what should be public sector goods. The logic of outsourcing work to NGOs is in essence the logic of privatization. Weaving that directly into your policy-making apparatus will bring you into conflict with, for one thing, many public sector unions; but on top of that, it will conflict with a vision of a sewer socialist future (assuming that is in fact your vision). And to make matters worse, a city that does not re-municipalize services is one that will always be prone to the vicissitudes of grant funding; when big foundations’ interests change, so will the interests of the NGOs they sponsor and underwrite, potentially bringing your NGO staff into conflict with your agenda.
The Lawyers [Devil Emoji]
Behind all of these departments, standing in the shadows in robes which if you poked them with a broom would collapse empty on the ground like when Obi Wan Kenobi became a Force ghost, are the city’s various lawyers. We’re overstating it maybe. But take it from a member of that particular priesthood: lawyers are small-c conservative. Not because they’re (we’re) bad, but because that is what training in American law does to them. They’re trained, first and foremost, not to get sued. Then after that, they’re trained to not lose. Then after that, they’re trained to not get yelled at by judges. Way down that list somewhere is “achieving your client’s fondest dreams.” Not because lawyers don’t want to zealously represent their clients’ interests, we do, but because somewhere deep down, your lawyers think they know your interests better than you do. The law, particularly municipal law and the traps of state and federal law and constitutional doctrines thrown into the mix, is extremely fraught. It is your lawyers’ job to make sure you don’t trip any wires.
So the lawyers from your Law Department, or corporation counsel, will advise you conservatively. They’ll tell you something is preempted by state or federal law. They’ll warn you that such-and-such program raises constitutional takings or due process issues. They’ll say that the ordinance you’re suggesting will invite litigation, will run afoul of existing agreements, and on and on and on. But they’re not even your biggest problem. Each department will have lawyers, the City Council will have lawyers and — here’s the big one — every interest group, trade association, and major developer or investor will have a gang of lawyers, each of them showing up to explain to you with varying levels of patience why you can’t do what you’re doing.
Or, worse, they’ll seductively counsel you, in the most congenial manner, about why you should do x. All without you realizing, of course, that x is not by any means your only course of action and is, in fact, terrible.
And the only cure for the lawyer malady? More lawyers. New York City’s Office of the Mayor alone has no fewer than 13 counsel. You need your own lawyers to tell their lawyers that, in fact, you can do what you want to do. Or that their suggested route of settling this or that lawsuit is a bad idea or that the risk of bad precedent is worth it. And your lawyers better be at least as smart as theirs — or, if nothing else, much better at bluffing.
DO: Understand How You Got Here
The worst mistake you can make when you’re facing down the forces standing in the way of your agenda is to misunderstand the nature and strength of the forces backing you up.
All mayors take their own special path into office. No two mayors are the same, not even the father-son pairs. One thing is always the same: the means by which you achieved this special position are the initial levers through which you will have to govern, while simultaneously being the engine that expands your governing coalition. At least at first, the coalition that puts you into office will define the political support behind your agenda. Therefore, your agenda needs to not only reflect their interests, but also, to some degree, be limited to the things that this coalition will mobilize to defend against the inevitable attacks, slanders, and fabricated scandals.
When you’re taking stock of your base to determine (a) what they want; and (b) what they’ll stretch to support, do not make the mistake of confusing people who voted against your opponent for the people who voted for your vision. The latter group you should be able to rely on; the former group you still need to win over.
People are fickle and political communities are complex. The idea that you speak on behalf of people because you have their best interests at heart is the type of nonprofit industrial complex thinking that has bedeviled the left for half a century. You need to win them over to you, and rhetoric alone doesn’t do that.
We can impart this by way of examples. Chicago has a non-partisan system whereby the top two vote getters move on to a second round, if no one candidate gets 50%+1. Therefore as a practical matter, the first round is the “base” round — the round where a candidate gets the people voting for something. The second round is where people choose the better of two available options — where people are just as likely, if not more, simply voting against something.
In 2019, Chicago had an open election with no incumbent. Lori Lightfoot was an “outsider” candidate (in the sense that she had never held elected office and wasn’t part of any political organization).
Lightfoot squeaked through the first round, but won an astounding blowout in the second round against Cook County Board President Toni Preckwinkle, a long-time progressive well-known to a voting public that was in an anti-establishment mood. Lightfoot took her second round blowout as a mandate and acted as though the City Council and various other groups, like the Chicago Teachers Union, needed to get in line. As a result, her popularity plummeted almost immediately, and a bloody fight with the CTU galvanized progressives against her.
Chicago’s 2023 mayoral election saw a crowded field vying to replace Lightfoot. In the end, there were four competitive candidates: Lightfoot herself, Congressman Chuy Garcia, former school privatizer and proto-Republican ghoul Paul Vallas, and County Commissioner and former Chicago Teachers Union staffer Brandon Johnson. These were two Black candidates (Lightfoot and Johnson), one Latino (Garcia), and one white (Vallas, who is of Greek ancestry). After the first round, Vallas and Johnson were left standing.
In the first round, Vallas relied on the wealthy and reactionary vote. Johnson got through the first round based on his support from progressive, white “lakefront liberal” wards. Numbers bear this out: there are about 1,300 voter precincts in Chicago, and 79% of the 325 precincts where Johnson got the largest number of votes were in white-majority zip codes. Johnson’s financial support was also narrow. He raised $10.5 million during the election, about $150,000, or 1%, of which came from direct small-dollar donations under $150. More than $8 million came from a handful of unions, most of which had not held member endorsement votes. By way of comparison, Zohran Mamdani received contributions from some 27,000 individuals at around $80 a pop.
While Johnson won a comfortable 53% in the second round, his approval ratings since the election have not reflected that number. His base does not seem to have significantly expanded beyond his first-round voters. As was the case with Lightfoot in 2019, the anti-Vallas vote did not necessarily represent a vote for Johnson’s agenda.
Does this mean that a new mayor needs to “moderate” or “tack to the center”? No. Expanding your base does not mean appeasing your detractors. There are areas of overlap between your existing base and other communities of interest throughout your city. You need a methodical approach to expanding those concentric circles in a way that boxes out your implacable opponents.
There will be lots of unfair, fabricated, or blown-out-of-proportion scandals and challenges during your term. Count on it. When the first conflict between you and members of the City Council breaks out over some new property development, or tax, or federal issue made local (like immigration), who will come out onto the street to support you? Who can you call on to have your back? What are the practical steps between here (your existing coalition) and there (the coalition you need for transformative change)? These are questions you need to be able to answer on day one. Not just in the abstract — through statements or public positions — but through practical and organic connections to the actual people who compromise those politically very complex communities.
DON’T: Lie to Your People
This is maybe the most important one for a progressive — and especially a democratic socialist — executive. The institutions of capital are strong. It’s not just the Republican Party and a landlords’ association. It’s international finance; banks; massive investment trusts, institutional bond holders; property developers; too many to list. On top of that, there is an entire secondary set of institutions who are dependent, whether they like it or not, on those institutions of capital. For example, tradespeople rely on new construction and renovation. That means they rely on property development capital. If things aren’t being built and fixed, they don’t eat. Tradespeople are not your enemy, but anything you do that results in less construction means workers losing jobs.
The institutions of the left are, relatively speaking, weak. There are advocacy nonprofits, organizing NGOs, community service providers, and semi-party organizations like DSA. The strongest institutions are unions. But “labor” is not one coherent entity; it has a lot of factions with different interests. This is especially the case when you’re the executive, because you’ve now become the boss of many of those unionized workers. You’ll want to do your best by them, but the pie is only so big (see above, revenue). So already, from day one, at least some factions of the strongest institutions of the left are set in a technically adversarial relationship with you.
The other institutions of the left are advocacy and policy NGOs, which have expertise they can use to influence the media, but no ability to put mass numbers of people into motion. Then there’s the organizing nonprofits, which tend to be parochial; strong in a small area, but unable to mobilize constituencies beyond it. Finally, you have the community service nonprofits, who have expertise and organic connections to various communities (e.g., community health care facilities can reach large numbers of people through soft influence), but who have a material interest in keeping their funding and maintaining their role in the provisioning of services — services which should be public.
This means that you, your office, will be one of the strongest institutions on the left, in your city if not more broadly across the movement. Your actions can build democratic socialism, but can also warp it. That happens when you exert downward pressure — “message discipline” — on your coalition to hide your weaknesses or treat your losses as wins.
You need to find the fearlessness to be open and honest with your base. If you want to hold on to your base and grow it, don’t lie. If something isn’t what you wanted, but you’re settling for it, say so. Don’t tell the people who sweated for you and believed in you that, in fact, the compromise you’re making is the thing you really wanted all along. That, actually, this outcome is better for them than whatever it was that inspired them to fight for you in the first place. People might not always know why what you’re saying isn’t the truth, but they can just about always tell that it isn’t. People know when they’re being hustled.
We’re not naive. We know that for many Americans, the worst thing an executive can be is ineffectual. We’ll forgive just about any villainy so long as somebody appears to be good at their job. It’s why people liked Tony Soprano so much. So how can you be honest about accepting a compromise, admitting that you weren’t able to win the full demand, without looking like a weakling?
When we talk about “speaking to” your social bases, we don’t just mean talk. To hold close the forces that are backing you up, you need real decision-making mechanisms and spaces where you can explain your challenges and develop ideas for solving them from the people in political motion. This doesn’t mean co-governance theater that merely appoints people to advisory boards. Those boards serve at your pleasure; your power means their ability or willingness to oppose you is minimal. The co-governance needs to happen in venues with real stakes, where your people feel true ownership over the process.
That doesn’t mean “tables” where organizational leaders anxious to keep their proximity to power advise you. It means larger structures filled with people with skin in the game. That can be an organization like DSA but only partly. You need union members and front-line workers and informal neighborhood leaders, people without titles, convened increasingly together. This is maybe the most important thing your office can do. And in the great tradition of democratic socialist politics it contains a contradiction, because not only is this type of structure most likely to protect you and advance a vision but also the most likely to knock your structure out from under you if you fail them.
When you feel that fear of falling, you’ll know you’re on the right track. That is how you know power is shared, not lent.
Trust that people will be reasonable. They want to see you succeed. Trust that they’ll credit your account, even when you’re drawing heavily against it.
Don’t ask your base to soft-pedal things for you. Don’t make liars out of them. Trust them, and trust the people. Some will be turned off by your apparent weaknesses. Others will wait for the first opportunity to call you a sell-out. But the people you empower by trusting them will be the greater number and their commitment will overwhelm everybody else.
There is a spiral that happens, particularly on the left, which is a symptom of the top-down, NGO-ified nature of left politics. The people at the top, to maintain their credibility, feel the need to embellish, exaggerate, or outright lie about their wins. In doing so, they drag their coalition partners down with them, trying to enforce “message discipline” and keep everyone “on the same page.” As a result, a disconnect forms. The “constituencies” are not too stupid to remember when the outcome hailed as a victory today was described as a defeat yesterday. They feel the lack of trust. It tells them that their leadership sees itself not as comrades, but as shepherds, waving their staff to guide their flocks into the pen. That is a fundamental defect of top-down politics, and a reason why bases so quickly evaporate on the left.
You’ll have to learn to play those difficult notes between trumpeting your advances and muting your defeats. It’s true, showing weakness will hurt you. Find a way to make telling a hard truth appear as what it really is — strength.
