One-sided Conversations with Unmedicated Alderpersons

I’m calling this a “pseudo-legitimate” dispatch because even though it’s entirely fact-based, I'm not an official reporter and I didn’t tell anyone I spoke with I intended to write about our encounters. As such, many identifying details have been withheld to protect the innocent — and unmedicated.

I enter the main door of the non-denominational church and head downstairs to the meeting area. It looks like most weekday events at most off-brand churches. Sporadic standing tables scatter about with groups of similar-looking people with similar-minded policy beliefs talking to one another about similar-sounding ideas.

Each Alderperson (or their staff) has set up shop at one of the many folding tables propped up around the perimeter of the room. Pamphlets abound. They all feature surprisingly unflattering pictures of their candidate making bold, declarative statements.

These are designed to persuade the not-quite-uninformed masses they’re the best person to “turn this city around” or “get this ward back on track.” Most contain a QR code for the middle-aged.

Centered in the back of the room, dozens of unopened pizza boxes sit stacked like library books on a folding table, their contents tepid and congealing.

I grab an open table close to the wall and survey the scene. Moments later another youngish man enters the fray and I immediately latch onto him. I’ll refer to him as “Wingman” for the remainder of this transmission.

Wingman and I exchange pleasantries, discuss the neighborhood, and talk about where we live without providing our specific addresses. Two other youngish men from a local neighborhood association join our conversation. As middle-aged people are wont to do, we discuss our kids and the neighborhood and our respective public schools.

The two association gentlemen move along, then Wingman tells me his wife’s expecting their first child. After honoring the social contract by congratulating him, I do the responsible thing and warn him. Wingman’s life will soon be over, and somebody needs to be honest.

I point to my own haggard face as evidence of how parenthood can devastate a once functional adult. I then offer my two pieces of unsolicited parenting advice:

1. All parenting advice is bullshit. Tens of billions of people have managed to keep their children alive for tens of thousands of years with a fraction of the resources at our disposal. You’ll be fine.
2. Your ex utero child will possess agency and its own personality. No matter what you do, some aspects of your child’s persona will remain unalterable. They’ll almost certainly be the things you hate most about yourself, which will exhaust and terrify and traumatize you for the rest of your life. There’s nothing you can do to change this fact, so accept it. You’ll be fine.

With Wingman and I properly acquainted, and the tone for the evening properly set, the festivities commence.

The informal event is a “Meet & Greet” between the community and the six Alderpersons running for election, but because humans can’t help themselves or learn from past mistakes, we’re forced to listen to everyone’s elevator pitch first.

After the opening candidate speaks I whisper to Wingman “I hate this type of bullshit” and retreat to the back of the room so I don’t have to look engaged. I jot down notes as I listen to the five remaining Alderpersons and am alarmed to learn I live in a war-torn, crime-laden, dystopian hellscape, and I’m very likely to be murdered walking home from tonight’s event.

That’s news to me, since I thought I lived in one of the wealthiest, safest neighborhoods in America. You really do learn something every day.

The elevator pitches conclude and I’ve already ruled out three candidates. One male candidate presents as alarmingly disingenuous — even by politician standards — and since there’s zero chance he’ll get my vote there’s no need to speak to him. Plus he gives me the heebie-jeebies.

The other two are the women candidates.

I briefly wonder if I’m part of the equality problem before remembering I voted for Hildog in 2016 and Lightfoot in 2019 (reluctantly) and donated to Elizabeth Warren’s 2020 campaign right before she got smashed on Super Tuesday.

I congratulate myself for my progressive bona fides and decide these two candidates — one of whom has been running for this same position since I was in high school — simply aren’t selling what I’m buying.

My perch in the rear is situated right next to the current Alderperson’s table. Sans Wingman, I mosey over and ask the young man sitting there why I should vote for his guy. My intention is to probe indirectly and see if I can get this person to say anything interesting.

Alas, my local representative materializes and shakes my hand vigorously and smiles toothily and is just so thrilled to meet me. He’s polished and professional and disciplined. I ask him if the crime thing’s really a big deal and he says “It is” and talks about the need for more policing, and hiring more police officers, and improving city-wide lighting, and implementing a “data-driven” approach to crime prevention. He’s got a background in tech and reminds me of the Silicon Valley types I frequently encountered during my years in San Francisco.

I ask him about reducing and eliminating the root causes of crime by making the city more equitable. How might we do that? I wonder. He sticks to his talking points about economic growth and economic opportunity and new business development. It’s predictably dull and replete with platitudes.

I eventually make haste, conceding he’s a savvy politician and — as the appointed incumbent — a solid bet to retain his position. I won’t vote for him, but I won’t be concerned if he wins.

Wingman and I reunite at a table in the middle of the room. He’s talking to two women — one Caucasian and one Black — the latter of whom is a generation older and wearing an N95 mask. I introduce myself and shake their hands and immediately forget their names and say I spoke to our current Alderperson and he’s good at talking a lot without saying anything meaningful.

Then I mention my frustration with everyone’s fearmongering about crime rates and tell them I don’t buy the argument that more cops will reduce crime, though it might displace crime from this particular neighborhood.

They seem impressed by my know-it-all attitude and say I have a good handle on the issues and ask why I’m not running, to which I respond, “I wouldn’t be caught dead doing this shit.”

The Caucasian woman laughs and says, “Good for you.”

I tell them I came to this event mostly to entertain myself and ask them — aside from the wanton violence desecrating our once proud city — what they’d like me to press the candidates on. Both immediately agree the planned marijuana dispensary will destroy the neighborhood and must be stopped at all costs.

I admit to not knowing anything about the Weed Dispensary Crisis of 2023 and ask why it’s a big deal.

They both bemoan the planned location — a derelict building around the corner from the church and opposite a large playground — and imply “the process” for granting the license was somehow corrupted.

Wingman cautions to suggest opening a dispensary in the neighborhood shouldn’t be seen as a bad thing. He says any new business is better than leaving the building vacant, which has allegedly been the case for over a decade.

The Caucasian woman says, “Well, if crime is the major issue of the day, opening a dispensary is the wrong choice. There’s studies — real studies — that show opening dispensaries causes crime rates to increase in the surrounding area.”

Wingman nods along bemused. As a former academic and present skeptic I know these oft-cited “studies” probably don’t exist, or are biased, so I don’t bother asking the obvious question and instead go with, “Interesting. A dispensary opened up near Wrigley last year in a high-traffic area. Have there been any significant changes in crime rates there?”

“Well, that’s like a different neighborhood,” she says.

The Black woman jumps in and laments the dispensary choice on apparent moral grounds. “Opening a dispensary there — next to a playground — it’s like opening an adult book store.”

I don’t have the heart to tell her nobody reads books anymore. Or that everyone watches porn online. Or that any kid with a TikTok account has seen more horrors than the Faces of Death franchise. So I settle on “That’s fair” and tell them it was a pleasure meeting them and I’m heading off to antagonize another candidate.

Wingman and I select our next victim. During his elevator pitch this candidate implied his prior experience playing football at Notre Dame was a qualification of some kind.

Before I can launch my first volley a rotund stranger shoves a pamphlet into my hand and tells me he’s running for some newly created citizen oversight position which will evaluate the performance of the police department — or something.

I say I’d never heard of that and ask if he has any prior experience as a police officer. He says no cops are allowed to run for the post — which I agree is a good thing — and then heaves a dry cough all over me and his face turns beet red and he assures me he’s “fine” and any day now I’ll test positive for XBB.1.5.

Wingman and I return our attention to Rudy. I ask when he played for Notre Dame and say I went to Michigan and he quickly admits he was a walk-on and didn’t dress for his only game at the Big House, which they lost and was “brutal. Wingman then reveals he’s an Ohio State graduate and suddenly all three of us eye each other with heightened suspicion.

I tell Wingman “we’ve” gotten the upper hand on the Buckeyes the last two years but that doesn’t begin to offset the seventeen-year losing streak “we” endured but he’s not having it and admits he’s rattled.

Rather than asking Wingman when Ryan Day will be fired, I stay on topic and ask the candidate if this whole crime thing is “bullshit.”

He says “No” and declares that crime in our ward is “as bad as it’s ever been.”

“Ever?” I say.

“Well, not ever,” he backtracks. “It was probably worse in the eighties, during the crack epidemic.”

We debate the actual crime statistics and policy responses and whether increased police budgets reduce crime or not. I suggest at one point that increased police funding has been accompanied by increased crime rates, indicating police spending and crime rates are positively correlated. I then joke that increased police spending might cause additional crime.

He smartly evades but I continue to press him on whether spending more on cops will actually reduce crime, at which point he pivots to his talking points on economic growth. I ask him what — tactically — he’d like to see implemented to increase economic opportunity across the city.

He ventures down a winding exposition about bundling and securitizing loans and then tranching them off to entrepreneurs to encourage small business creation. In the middle of explaining his proposal he admits “it sounds bad because it’s basically like a collateralized debt obligation” — the financial instrument responsible for causing the 2007-09 financial crisis — but stresses that more people need access to capital in order to start small businesses and make a living.

Intrigued by his outside-the-box thinking, I say I agree access to capital is a major challenge and kindly suggest he change his messaging to focus on “economic growth as a means to increase equity and reduce crime.”

He likes that idea. I say he seems like a nice guy but re-emphasize his message of being tough on crime doesn’t resonate with me because everyone says the same thing and his primary selling points aren’t differentiated. I acknowledge total crime is higher than its recent lows, but it’s not as bad as politicians portray it to be, hence why I think all this panicking and pandering is bullshit.

“It is bullshit,” he says. “And it is overblown. But that’s what people care about so that’s what I’ve got to run on.”

We shake hands, I suggest one last time he modify his messaging, and wish him well.

Finally, with the event winding down, Wingman and I make a beeline for our last target. He’s just finishing a conversation with another unmedicated voter when I shake his hand and introduce myself.

Running short on time, I say, “Real talk: this whole crime thing is bullshit, right?”

“Let’s talk over here,” he says, and guides Wingman and I to his station away from earshot of the other candidates.

I pursue the same line of questioning as before, and we launch into a lively, engaging discussion. This candidate talks about equity, and equality, and opportunity, and using the financial heft and influence of our ward to help drive positive change across the rest of the city.

Policy specifics and granular details are expectedly light, but philosophically I like what I’m hearing and tell him he’s the first person I’ve met who’s “speaking my language.”

I continue to press him on the alleged need for more cops, however, and how there’s little evidence to suggest more cops will positively influence crime rates. Then I tell him I don’t want a police officer manning every corner of every street in our ward because I’m worried my few Black neighbors will be harassed — or worse — because they don’t look like they “belong” in the neighborhood.

At this point I remember to mention the private security detail my dipshit neighbors on the adjacent street pay for, which directs one dude in an SUV to drive around the neighborhood every night and flash bright green lights through my living room window.

“I don’t want to feel like I’m living in a police state,” I say.

Here, he pushes back and says we do need more police walking the beat, but we need them to be actual members of the community. And they need new types of training.

“You mean like McNulty walking the streets in season four of The Wire?” I say. “Because if that’s what you mean, sure, I’d love to meet my local McNulty. You’ve seen The Wire, right?”

He scoffs, then excitedly says, “That’s my show.”

“I’ve seen every season twice,” I say.

He’s impressed by my commitment and we briefly bond over our mutual love for the best TV show ever before shaking hands again. 

Another concerned citizen snags the candidate’s ear while I talk to a separate candidate for the new police oversight position — or whatever it is.

She’s young and energetic and smart. We agree civilian oversight is crucial for a functioning society and discuss how adverse selection plagues much of public service. I’ll vote for her.

With the event past time and the modest crowd dispersing I double back to my favorite candidate with a question and a confession.

“I know you’re not supposed to take sides, but who should I be looking at for mayor?” I ask. Ever the diplomat, he says there’s lots of great candidates running — naming two I’m familiar with — then says he’s a big fan of Kam Buckner. I don’t know who that is but the name sounds vaguely familiar.

The candidate says he’s trying to organize a local event for Buckner. I say to keep me in the loop and ask him to grab his phone. I open my QR code app with all my contact information. He snaps a photo of the image, I push the button on his phone to add me as a new contact, then say, “You know, I actually write humor and satire and came here tonight for ammunition.”

He laughs, then I say, “I’m gonna make fun of this event on my newsletter. But don’t worry. I won’t make fun of you, because I like you. But I will make fun of other people in attendance tonight.”

He says he wants to check out my writing. I add him as a free subscriber.

We shake hands one last time.

He’s got my vote.

Bonus material

A local event on January 17 informed the story above, but I also attended a separate Q&A forum on January 24 which was presided over by a moderator.

Unfortunately, it proved largely unremarkable save this gem.

When asked to provide policy prescriptions for reducing gun violence, one candidate went on a rambling soliloquy about attending college in the U.K. around the time John Lennon was assassinated. They concluded their nonsensical rant with:

“I can live in a country where they shoot the politicians, but I can’t live in a country where they shoot the musicians.”