The New York Mayoral Circus: A Portrait of Political Delusion

I spent Tuesday morning doing what any reasonable person does at 3am—hunched over my drawing board in my New York studio, drawing portraits of (mostly) grown adults who aspire to run this here city of New York.

This is how I work best: caffeinated, ink-stained, panicked and making artistic decisions with the deranged confidence of someone whose caricature of his landlord was so accurate it got him evicted. (Different story. Different apartment. Different decade when I could still afford rent without selling a kidney. I really shouldn’t have hung it on the fridge. I knew he’d see it.)

The assignment seemed straightforward enough: Eleven challengers, one incumbent, draw 6 of them. But as I started sketching, I realised I was essentially drawing a lineup of people auditioning for the role of captain on a sinking ship—except the ship is also on fire, and half the passengers are arguing about whether water is wet.
Spoiler alert: it’s not water.

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I bowed out of political cartooning for a little while towards the tail end of the Obama years. A satire sabbatical. I started out when I was a teenager, drawing editorial cartoons for my hometown community papers in Perth and Fremantle. As the decades rolled on and things got a little insane with social media, I recoiled. I withdrew when malicious trolls grabbed hold of people’s cartoons and spread them wider than their intended audience. It got pretty ugly. They were taken out of context, torn to shreds and—worst of all—recaptioned with racist, homophobic and sexist propaganda. (They would keep the signature intact. Bless them.)

But then along came the jolly orange giant, and I couldn’t keep my drawing hand from shaking. I snapped four pencils trying not to scribble something about the bedlam of 2016.

Then the President blocked me on Twitter.

It was back on, and I took my political pen out of retirement. He insulted my writing partner and me with the ultimate burn in response to one of our cartoons about him in the New Yorker— “Oh, I love it!” he belched between sips of Diet Coke. Worst day of my career.1

Anyway. Back to this new commission.

Allow me to walk you through the rogues' gallery…

I’m ranking these in order of how much ink I had to spend to get their portrait right. There is no bias here. Apart from the all-encompassing bias I have as a cynical New Yorker scraping by in the heaving heart of Hell’s Kitchen. I squint at all politicians equally.

First up: Zohran Mamdani, the 33-year-old socialist assemblymember who's gone from polling at 1% to trailing Andrew Cuomo by just two points. (Eep!) Drawing Mamdani was like trying to capture earnestness incarnate—the kind of face that says "I genuinely believe we can make buses free" while also saying "I've definitely cried at a Chapo Trap House live pod." His supporters include a group called "Hot Girls for Zohran," which sounds like something I would have started as a joke in 2012, except these people are serious and also absurdly attractive.

The technical challenge with Mamdani was capturing that specific brand of Brooklyn socialist optimism—you know, the look of someone who can quote both Marx and their tele-therapist in the same sentence. I started with pencil on paper, scanning it into Photoshop, then spending forty minutes trying to decide if making his eyes too hopeful would be read as mockery or admiration. (I went with somewhere in-between. I'm not a complete monster.)

👉

Olivia Reingold

just wrote a great piece on his steady rise this week.

Then there's Andrew Cuomo, who's running despite the fact that everyone seems to have collectively agreed to pretend his governorship ended with him gracefully retiring to write cookbooks with his mother, rather than... well, you know.

Drawing Cuomo is like drawing a thumb that went to law school—there's something inherently comic about that face, those brows that look like they're constantly asking "You talkin’ to me?" even when no one is talking to him. I tried to capture what I call his "institutional certainty"—the expression of a man who's never doubted his own brilliance despite overwhelming evidence to the contrary.

I feel very conflicted about this one. I was living in Manhattan through the pandemic, and the daily, candid briefings from Cuomo were oddly comforting (until they weren’t). New Yorkers who lived through that time are still traumatised from the nursing homes, and seeing the freezer trucks out on the streets, stacked with the corpses of their neighbours. I certainly didn’t shake it.

Oof. Heavy. Sorry.

Oh, and before you’re all like “Jason, these are amazing!” just take a look at the incredible Richard Thompson’s caricature of Andrew’s dad. Settle down— I’m a guppy next to this mad genius:

Eric Adams, our current mayor, was paradoxically the easiest and hardest to draw. Easy because his face has achieved a kind of political ubiquity—I could probably draw those cheekbones in my sleep. Hard because how do you capture the essence of a man who seems to exist in multiple realities simultaneously? This is someone who can deliver a speech about veganism while possibly being photographed at a steakhouse, who can talk about living in New Jersey while swearing he sleeps in Brooklyn. (Carefully removing his earring before hitting the pillow.)

My solution was to lean into the uncertainty. I gave him the expression of someone who's just been asked a simple question about where he lives and is calculating seventeen different ways to answer it. The portrait ended up looking like a man permanently mid-pivot, which feels right.

The other candidates blurred together in that way that New York political also-rans tend to do—a collection of real estate developers and former commissioners who all seem to shop at the same "Serious Candidate" section of Spirit Halloween. Drawing these suits was like creating NPCs for a video game about municipal government— Important enough to include, not interesting enough to remember.

Drawing Scott Stringer felt like sketching someone who was born wearing a rumpled windbreaker and muttering about pension reform. There’s a kind of bureaucratic weariness baked into his whole vibe—the look of a man who’s spent decades in city government and has the calluses to prove it. He’s part public servant, part human spreadsheet.

Listen. I have respect for anyone who has served as the City Comptroller. (2014 to 2021.) Mainly because I have no idea what the fuck a comptroller is or what they do. But definitely sounds like a job that needs to be done by someone named Scott.

Anyway. I feel like his energy is less “mayoral aspirant” and more “disappointed high school civics teacher.” I tried to capture his signature expression: a man who’s spent a lifetime in city government and miraculously isn’t dead inside—a quiet, almost endearing hopefulness, like he’s just jonesing for someone to ask him about the capital budget so he can light up. His shoulders slouch like a guy who’s been through 40 budget cycles, but his eyes say, “We can make this city better—if you just let me audit something.”

Sidenote: I seem to recall him dropping out in 2021 due to a scandal of some kind? Hit me in the comments if you can remember.

Drawing Adrienne Adams was like trying to capture quiet authority in ink. She has the expression of someone who’s seen the political storm, read every line of the budget, and still made it to the meeting on time with earrings that match. There’s no grandstanding in her face—just a kind of practised poise, the look of a woman who’s heard every excuse and isn’t in the mood for a new one. In the portrait, I leaned into the calm clarity she carries—head turned slightly, eyes scanning some distant fuckery she’ll soon have to clean up. If the other candidates are chaos in motion, Adams is the eye of the storm: centred, steady, and probably holding the only working copy of the city’s strategic plan.

Before you think this reads as some kind of ringing endorsement, of course, poise can also be a double-edged sword. For all her calm, Adams sometimes leads like someone who’d rather broker peace than start a necessary fight. In a city full of screamers, she’s a whisperer—and not everyone hears it.

Brad Lander was a different kind of challenge—less “how do I capture this man’s soul” and more “how do I draw a face that doesn’t look like he just smelled something in the empty subway car?” Lander looks confident, despite the fact that he just found out the city budget is being held together with duct tape and deferred trauma. He’s pretending it’s totally fine. Lander is the guy at the meeting who’s already anxiously read the packet, annotated it, and brought muffins. In the drawing, I gave him the eyes of a man who’s spent many evenings in community board Zooms and still believes in the democratic process, which is both noble and frankly a little heartbreaking. If Mamdani is hope and Cuomo is hubris, Lander is that quiet, panicked voice whispering, “Okay, but we’re going to figure out how to pay the check, yes? …Guys? Ok, no, you go on ahead, I’ll catch up with you.”

The whole exercise reminded me why I both love and hate this city's politics.

Where else would you get a mayoral race featuring a socialist with a stan army, a disgraced former governor attempting a comeback, and an incumbent who may or may not live in the city he governs?

I was honestly a little disappointed I didn’t get to draw Curtis Sliwa in his goofy little red beret. I guess I’ll have to wait until he, as they say in my hometown, pulls his finger out. When you’ve worn the same hat for 40 years, it’s either a personality or a political platform. Drawing him would be less about likeness and more about capturing the essence of a man who believes yelling “NO TO CRIME!” on a bullhorn outside a subway exit counts as a housing policy.

Mamdani thinks we can have European-style social democracy in a city where the diarrea-filled subway can't even run on time. Cuomo thinks we've all forgotten why he left. Adams thinks we believe he lives here.

And me? I think I need stronger coffee. But I'll keep drawing these beautiful disasters, because someone has to document this depraved circle of municipal hell. Even if that someone is a 40-something Australian who can barely afford to live here and definitely can't afford to leave.

I submitted the portraits right as my upstairs neighbour began their daily ritual of apparently teaching rhinos how to tap dance. Looking at them all together, I realised I'd inadvertently created a portrait of Democratic dysfunction—each face a different flavour of delusion about what this city needs or what they can actually accomplish.

The portraits are live now on

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