A Tale of Two Mayors: Chicago vs. New York

The old failure vs. the failure-to-be

A bunch of politicians have been commenting on things that they have no power to deal with.

They might as well, given they do not seem to have the ability to deal with the jobs they were actually elected for.

I am singling out the mayors of Chicago and New York City.

3 Jan 2026, on X, Brandon Johnson, mayor of Chicago:

3 Jan 2026, X, Zohran Mamdani, Mayor of NYC:

Mamdani got roundly mocked for the “briefed”. He probably means somebody woke him up and told him to read the news online (and most likely read it on X).

Now, I have nothing particular to say about Venezuela, as it falls beyond my area of expertise.

But really, nobody is that interested in the foreign relations opinions of mayors.

It is semi-relevant that Maduro is being held in federal lock-up in NYC… but not really. The feds do all sorts of things in NYC — and so does the United Nations. The mayor of New York can’t do much about either. Ask about the parking tickets.

Let’s take a look at what their jobs actually entail, and how they have failed or are going to fail at it.

Mayor of Chicago: Set Up to Fail, and Failing Even Worse Than That

I want to be fair to Brandon Johnson.

As I wrote when he became mayor of Chicago:

Brandon Johnson is going to be finding himself in a very hard place, because the Chicago pensions have made some very large promises, which have accrued … and the underpayments to those funds have continued to snowball.

Johnson’s grand ideas of spending plans will get undermined by the need to pay for these pensions.

I have sympathy for him because he’s actually going to have to deliver on operations, and he’s going to find the “rich” people he wanted to squeeze for revenue have become thinner on the ground. Maybe he can tax some of the highest-paid public employees. Let’s see how well that will go over.

Tell them it’s for their pensions.

We’ve seen what he’s done since May 2023: attempt to tax more more MORE, and getting shot down by the state (governor and legislature)…. then getting shot down by the aldermen.

I had a few posts on Johnson’s proposed return of the Chicago head tax:

• 12 Dec 2025: Chicago Watch: Head Tax Hostages, Credit Ratings, and Reactions

• 3 Nov 2025: Chicago Head Tax: So Many More Reactions

• 28 Oct 2025: Chicago Head Tax (and Other Taxes) Proposal: Reactions

• 17 Oct 2025: Chicago Mayor: Stupid Tax Ideas as the City Stares into the Abyss

While Johnson and his allies kept trying to sell this as a “soak the rich” strategy, it doesn’t work this way… and I don’t need to revamp those arguments at all.

Because the whole point was a way to raise revenue that didn’t require him to go begging to Springfield. Johnson hates talking with Pritzker or any other Democrats in Springfield. It’s obvious.

Or, perhaps, none of them will take his calls, and he’s gotten the signal.

The hate may be mutual. Fair enough.

It also turns out that the Chicago aldermen had enough of Johnson’s crap, and they passed their own budget, which Johnson decided not to veto.

22 Dec 2025, Block Club Chicago: City Council Passes 2026 Budget: Here Are The Major Fees And Changes

Alderpeople on Saturday [Dec 20] passed the final spending portions of the so-called alternative budget proposal that made its way through City Council despite sharp objections from Mayor Brandon Johnson and his allies.

The overall package avoids implementing a corporate head tax while making a full advanced pension payment, two provisions the group of alderpeople backing the proposal identified as among their top priorities.

The passage of the 2026 budget is a major rebuke of the mayor by the City Council, although Johnson could still issue a veto or attempt to amend it in various ways.

21 Dec 2025, Axios: Chicago alders pass budget without head tax

It’s not a fabulous comparison, but it will do.

As I mentioned before, Johnson did not veto the budget, but he was whiny about it in not signing it:

27 Dec 2025, ABC7 Chicago: Mayor Johnson to move forward with alternate Chicago budget, signs 2 executive orders

Chicago Mayor Brandon Johnson on Tuesday morning said he would move forward with the alternate budget passed by Chicago City Council on Saturday.

Johnson said he would not sign the budget, but it will still take effect five business days after the vote, his spokesperson said.

Johnson said he would not cause a city shutdown.

By allowing the alternative budget to become law without his signature, he’s attempted to have it both ways, calling the budget a win, while also continuing to denounce parts of it as immoral.

Johnson convened a large group of supporters to City Hall to celebrate a budget he denounced as late as Saturday.

….

Johnson continued to blast a provision that would allow the city to collect millions of dollars of debt Chicagoans owe for things like city ambulance payments, utility bills and red-light cameras.

“It is immoral to send debt collectors after working people at a time when Donald Trump is attacking poor people,” he said.

He also signed two executive orders Tuesday, including one on the sale of city debt.

The first order prohibits the sale of city-administered medical debt owed by individuals to private entities and sets clear standards for transparent and stable debt collection practices by both the city and private third parties, the mayor’s office said.

“How we choose to manage our fiscal obligations reflects who we are as a city,” Johnson said. “I’ve been clear from the beginning of this debate that I will not allow the sale of debt to lead to the use of predatory and immoral tactics against the people of Chicago. This Order affirms that the City will manage this debt in a manner that protects dignity of our residents, advances equity, and preserves public trust in our city government.”

I added the emphasis.

Yes, I know he was talking about using private debt collectors.

But seriously, given how poorly Chicago has managed its money, you would think he’d know how laughable that line is.

31 Dec 2025, WTTW: Chicago’s 2026 Budget Takes Effect, Forcing Chicagoans to Pay More for Shopping Bags, Uber Rides, Booze, Online Gaming — But Grocery Tax Eliminated

The $16.6 billion spending plan, which takes effect Thursday, closed a $1.19 billion gap without imposing a per-employee tax on large firms to fund violence prevention and youth employment programs.

….

But Johnson, who neither signed nor vetoed the spending plan, allowing it to take effect, has repeatedly warned that the budget is not balanced — with a $163 million deficit — and that the City Council may have to make emergency cuts to make up for revenue that does not materialize.

….

Chicago’s finances have long been out of whack, pinched by soaring pension costs, spiraling personnel costs and a massive amount of debt. Officials are staring into a financial abyss after hitting the so-called “fiscal cliff,” with Chicago’s federal COVID-19 relief funds exhausted and tax revenues lagging after a period of high inflation.

The budget sets aside $238.6 million to make an additional payment into the city’s woefully underfunded pension funds in an effort to avert a second consecutive credit rating downgrade.

Johnson had initially proposed paying just $120.8 million more to the city’s four pension funds, citing the city’s financial woes.

As part of the spending plan, the City Council approved a plan backed by Johnson to borrow $1.8 billion.

That includes $166 million to cover the cost of raises for firefighters who worked without a contract for four years, $283 million to cover the escalating cost of police misconduct settlements and fund the city’s infrastructure program for 2026 and 2027, which includes $144.6 million to repair bridges and viaducts, $174 million for street resurfacing and $173 million to replace lead service lines.

A lot of that borrowing is for operational costs! (Old or current)

Not capital costs! Argh!

Brandon Johnson’s leadership on the fiscal front has been underwhelming, as he tries to go it alone in pursuing his ideas for revenue boosts (and trying to avoid cutting anything).

It’s hardly surprising, given his background. He started as a teacher for a few years, became a Chicago Teachers Union organizer, being a major player in the Chicago teachers’ strike of 2012 and very active in the 2015 Chicago city elections. He was a Cook County commissioner before running for mayor of Chicago, though he was a fool to do so. I’m not sure he realized that it was a sucker’s prize.

The fun money is gone. It left with the Daleys.

It doesn’t help that the state boosted some pension costs for Chicago (police and fire), retroactively, so that’s going to be hitting cash flows in the future. That’s separate from the raises for firefighters.

The “good news” is that Johnson’s folks on the Chicago Board of Education managed to get their own tax increase voted in at the last minute in 2025, which should help with teacher pension costs, which are also high.

29 Dec 2025, Fox 32: Chicago Board of Education quietly votes to raise property taxes

CHICAGO - The Chicago Board of Education voted 15-5 to increase property taxes on Chicagoans by $25 million, the maximum allowed under state law, which puts a cap on yearly increases.

….

A moderate nonprofit group called Urban Center, which has been critical of Mayor Brandon Johnson and the CTU, had this reaction:

“Their ‘quiet’ action today at a board meeting few knew about during the holiday season, and conveniently after the mayor’s failed budget despite his claims of protecting Chicagoans from property tax increases, only serves to demonstrate board members’ contempt for taxpayers, who continuously foot the bill to pay for the demands of the Chicago Teachers Union, a Johnson ally.”

To make matters stranger, Fox Chicago was told by multiple sources on Monday that board president Harden called members into group meetings to complain about leaks to the media — namely Fox Chicago’s Paris Schutz who revealed that this meeting — a public meeting — was scheduled and would take place.

Fox Chicago learned that Harden vowed to force the resignation of any board member he discovered leaking this information.

I added the emphasis.

Not sure how Harden can force the resignation of any of these Board members. They’re elected now.

And it’s a public meeting. Not sure how one can “leak” public information.

It does remind me of this bit from The Hitchhiker’s Guide to the Galaxy:

“But the plans were on display…”

“On display? I eventually had to go down to the cellar to find them.”

“That’s the display department.”

“With a flashlight.”

“Ah, well, the lights had probably gone.”

“So had the stairs.”

“But look, you found the notice, didn’t you?”

“Yes,” said Arthur, “yes I did. It was on display in the bottom of a locked filing cabinet stuck in a disused lavatory with a sign on the door saying ‘Beware of the Leopard.”

Evidently, Harden is trying to back up his threats by hiring a non-Chicago law firm to try to investigate the “leaks” of public information. You can see this was very effective in intimidating the elected board members, because this not-as-public information immediately leaked:

6 Jan 2026, Chicago Sun-Times: CPS Board is investigating two leaks of internal board information

The Chicago Board of Education has launched two investigations into how internal information got into the hands of the media.

It is looking at whether a member is responsible for revealing the names of superintendent finalists to the media and how a reporter recently got an internal update that included information about plans to hold a special meeting to raise property taxes.

The board president is so incensed by the recent leak that he is threatening to ask the guilty party to resign.

Add the leakage of this investigation on top of the other two, I suppose.

The person (or multiple people) is not feeling terribly guilty, as you can see.

Anyway, it seems that Brandon Johnson has inspired multiple people, most of whom are definitely Democrats, to build up their own coalitions against his interests.

Brandon Johnson was not new to Chicago city politics, and yeah, he’s failing pretty hard.

Anybody coming in as mayor in 2023, dealing with Chicago, given its abysmal finances, was going to have to get a broad base of support if they were to succeed. It was always going to involve a lot of pain. The federal largesse from COVID funds was going to flow away, even if a Democrat won the presidency in 2024.

Even if somebody charmed at the state and federal level, the funds would not be forthcoming at the levels to make things comfy… and Brandon Johnson has been doing nothing but create enemies, even among people who used to be allies.

I have no idea who the next suckers will be to line up to be mayor of Chicago, or why they would want to. But at this point, it’s fairly clear that Brandon Johnson is unlikely to change his ways. He’s had plenty of chances to learn that he has to work with FELLOW DEMOCRATS.

And now he’s taught fellow Democrats to team up to work around him.

[golf clap]

That might save Chicago in the short term.

The long term… more on that later.

Mayor of New York: Failure-to-be Zohran Mamdani

Just a few snapshots.

Now, now, let’s be fair. Maybe Mamdani thought his “moral weight” could influence FIFA to free up some tickets for a lottery or something. (or maybe they’re already doing that… I don’t know. My sport is sumo, not soccer.)

The next is a little more serious in NYC:

So, Mamadani didn’t do that. The MTA (which is a state-level organization, not controlled by the city) did that.

And that’s the main problem with all of Mamdani’s jaw-boning.

As many people have pointed out, he ran as if he were Bart Simpson running for elementary school class president, promising no homework and free candy for everybody. But unlike Bart Simpson, he remembered the bit where he needed people to vote for him.

But so much of what he spends his time talking about… he has no power to control. At all.

Unlike Brandon Johnson, Mamdani’s “work experience” is extremely thin.

He was an “aspiring rapper”, per his Wikipedia article. I’m not going even to try to evaluate how realistic his “career” in that sector was. An entire paragraph is wasted on projects …that were his mother’s. So, yeah, I’m thinking he wasn’t getting much of anywhere in the arts world outside of his family’s support.

In the political sector, he’s been more successful because he’s a rich, good-looking guy. The socialists love those! Especially the young socialists!

He was in the New York state legislature for the years 2021-2025, having had experience of running unopposed in legislative elections (2022, 2024)! This is a fairly common experience in NY races for Democrats, especially in NYC.

The thing is, running elections and being in a legislature is very different from being the mayor of New York City. As fun as it is to give speeches, there are managerial things one needs to do as mayor.

I remember de Blasio running into this problem with the first major snowfall (though that was mainly the sanitation department throwing its weight around).

Again, most of the political players in NYC are Democrats, as with Chicago. As fun as it is to blame Republicans for all the evil things, most of the political fights are Dem-v-Dem.

The problems Mamdani will run into are unlikely to be the money ones, because he is hemmed in by what he is allowed to control solely, unlike the mayor of Chicago. For NYC to have money troubles, it takes a true group effort… and, alas, that may still happen.

But that’s for another time.

I focus on the money stuff, and Mamdani’s problems are likely going to be non-money-related, centered around various policy positions… especially as he’s decided to get involved in international relations.

If Mamdani messes things up so badly that it drives out the UN, that would be a plus, but I think that’s unlikely. The “international community” likes shopping on Fifth Avenue too much, from their various car services (ignoring their parking tickets).

However, most likely, everybody will just go to him for a quote, because they’re the media located in NYC, and he’s a pretty face … and he’s willing to shoot off his mouth about anything as if anybody cares about his opinion on Greenland or any other country.

The benefit is that it keeps him out of other trouble, though his staff will be trying to wreak havoc independently.

I’m glad I’m watching it from 70 miles away.