The 5 oddest moments as Chicagoans vote for mayor

A City of Brotherly Love. A City of Angels. A Charm City.

Chicago isn’t trying to be any of that. Exhibit A: This Tuesday’s mayoral election.

Concerns about crime have dominated the 2023 mayor’s race but the messy, nine-person race spawned a steady supply of campaign theatrics — even by Chicago standards. Two candidates got hit with the obvious red flags for using teachers and police officers as campaign props, and there was this thing about shooting rabbits. One perceived frontrunner in the field of declared Democrats has been pummeled as a secret Republican — the ultimate insult in a city that hasn’t elected a GOP mayor in a century.

Before this contest fizzles into a two-person runoff in April, here are the big, weird, lowbrow moments as voters cast their Election Day ballots:

Conservative Democrat — or Republican spy!

Former Chicago Public Schools CEO Paul Vallas is running to the right of Mayor Lori Lightfoot, politically squishy on abortion rights, pushing to flood the streets with more cops and getting the backing of the conservative Fraternal Order of Police. Although he told Block Club Chicago in mid-February that he is a “lifelong Democrat,” his rivals say everything adds up to being a Republican.

“What I feel like I am listening to is a version of Extreme Makeover: Paul Vallas Edition,” Lightfoot said during a January debate.

The speculation mainly stems from a 2009 interview, where Vallas said he was “more of a Republican than a Democrat now” and that he does not support abortion rights for religious reasons. He also said he was a fan of Rudy Giuliani during his presidential run at the time. Lightfoot ran with those sound bites, using the interview clips in an ad that closed with: “Paul Vallas is a Republican. Just ask him.”

Vallas accepted the Fraternal Order of Police’s endorsement by saying it represents support from the union’s rank-and-file officers, rather than its controversial leadership that has commended fatal police shootings, resisted vaccine mandates and posted inflammatory and racist things on social media.

‘Hunt them down like …’

Ever since his son was killed in a 1995 drug-related shooting, Willie Wilson, a perennial candidate who has run for president, Senate and another three times for mayor, has taken a strong anti-crime, police-friendly stance. But during a January debate, arguing that Lightfoot wasn’t doing enough to curb Chicago’s violence, he said she needs to “take the handcuffs off the police” and allow officers to “chase [somebody] down and hunt them down like a rabbit.”

The line instantly attracted jeers and is perhaps his most attention-getting moment of the race (even at his rallies).

Lightfoot said Wilson was unfairly targeting Black and brown men. Community activist Ja’Mal Green said it was “disgusting” to have an older man “who was a sharecropper from down South who would get on TV and constantly double down on hunting people down like rabbits.”

“I don’t respond to kids,” Wilson responded.

Wilson has a policing plan that includes bolstering police presence on city transit and installing more cameras throughout Chicago, but his main philosophy goes beyond that. “I don’t care what color you are. … I’m gon‘ lock ‘em up. And they get out again, we’ll lock ‘em back up. Because crime has no color,” Wilson told The TRiiBE in January.

Tricky Twitter fingers

The weekend before the election, the Chicago Tribune reported that Vallas’ official Twitter account had liked several inflammatory posts that bashed Lightfoot or had racist connotations. Some referred to the city’s first openly gay mayor as “Larry” rather than “Lori” and others made fun of her appearance and height, while another called her “beyond human.”

Still other tweets promoted “stop-and-frisk” policies as potential policing solutions — things that did not help dispel the idea that Vallas might be a Republican.

First, Vallas said he had nothing to do with those likes, as he doesn’t personally manage the account, and that his team was trying to identify who was responsible. Some of the liked tweets predate his campaign announcement, the Tribune reported.

The candidate told CBS News on Saturday that his account had been hacked altogether: “Even though we shut down our system; changed our password, they’re still trying to hack us.”

But he denied the tweets in question were “the R word” — or racist.

Civil service campaign fodder

The top four candidates in the race — Rep. Jesús “Chuy” García, Cook County Commissioner Brandon Johnson, Vallas and Lightfoot — dominated the airwaves during the election, with more than $7 million spent across 40 ads. But it was García, who ran for mayor before in 2015, who mishandled a TV spot, which included a clip of two uniformed CPD officers walking down a street with the candidate under the caption “fully fund community policing.”

The Chicago Board of Ethics said they were never consulted by his campaign on using images of uniformed officers ahead of the release. CPD’s policies state officers cannot participate in partisan or political activity, though their image can be used in campaigns as part of documenting a specific event. García later released a reedited version of his ad with generic images of a police car and law enforcement uniforms.

Lightfoot had her own public service dustup.

A letter from Lightfoot’s campaign team to CPS and City Colleges of Chicago employees in January sought to recruit student volunteers to “help Mayor Lightfoot win this spring.”

The emails were a “common practice to provide young people with the opportunity to engage with our campaign [and] done using publicly available contact information,” the campaign said in an initial statement. But Johnson and García panned the move as “desperate.”

Lightfoot later apologized, attributing the “mistake” to a “young staffer,” and that seemed to be it, only for the public to discover it wasn’t an innocent — if inappropriate — one-off. It was one of thousands.

Chicago news outlets found that Lightfoot’s campaign had been sending similar notes to city school employees for months. The requests included fundraising, invitations to town halls and requests for help gathering petitions — totalling almost 10,000 emails since April. Lightfoot’s team repeated that it was a mistake and that they had “long since halted any such recruitment efforts,” despite dozens of employees continuing to receive emails after the campaign said they had stopped.

The Board of Ethics is still investigating the matter and has not made additional comments.

Property wars

Few things are worse to a Chicagoan than someone mouthing off about the city only to find out they’re from the suburbs. WTTW reported in February that Vallas listed his permanent residence as an address in south suburban Palos Heights — a 20-minute drive from the edge of Chicago’s southern neighborhood of Beverly.

The county assessor’s office did look into Vallas’ residency but closed their investigation since a mayoral candidate only has to live in the city for a year before announcing their candidacy. Vallas says he lives full-time in the South Side neighborhood of Bridgeport, a 12-minute drive from downtown, while his wife is the primary resident at their Palos Heights home. Other candidates also own property outside the city limits, which made the episode feel like a waste of time.

That didn’t stop Lightfoot from getting in a jab while she voted early last week: “I’m glad my wife lives in the city of Chicago and can vote for me, unlike some.”