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Veterans day or heavyweight prize fight? Longevity vs. change in ward races

Top, left to right: Ald. Leslie Hairston (5th), 5th Ward challenger William Calloway and Ald. Ariel E. Reboyras (30th); bottom, left to right, 30th Ward challenger Jessica W. Gutierrez, 40th Ward challenger Andre Vasquez and Ald. Patrick J. O'Connor (40th). File Photos. | Rich Hein/Sun-Times

Top, left to right: Ald. Leslie Hairston (5th), 5th Ward challenger William Calloway and Ald. Ariel E. Reboyras (30th); bottom, left to right, 30th Ward challenger Jessica W. Gutierrez, 40th Ward challenger Andre Vasquez and Ald. Patrick J. O'Connor (40th). File Photos. | Rich Hein/Sun-Times

Between them they have a combined 72 years of institutional knowledge — of knowing where the bodies are buried —  but three aldermen could wind up being history if three challengers can write their political obituaries.

Ald. Leslie Hairston, who’s represented the South Side’s 5th ward for 20 years, is facing activist William Calloway, who was an instrumental figure in forcing the release of the shooting video of Laquan McDonald.

 In the Northwest Side’s 30th Ward, 16-year incumbent Ald. Ariel Reboyras is trying to fend off a challenge from Jessica Gutierrez, the daughter of former U.S. Rep. Luis Gutierrez.

 And Ald. Pat O’Connor, whose City Council  seniority is only surpassed by Ald. Ed Burke, is in his first runoff since he unseated Ivan Rittenberg to become alderman of the North Side’s 40th Ward 36 years ago.

The races are three of the 15 runoffs scheduled for April 2 because no candidate won a majority in February.

But Andre Vasquez, a statewide manager for AT&T and former rapper, sees his race against O’Connor as more like a championship fight.

In one corner, is “somebody who’s like fully trained, a multi-black belt, with all the amount of funding — and then there’s us.”

Ald. Pat J. O'Connor talks with Ald. Leslie A. Hairston during a City Council meeting in 2014. File Photo | Al Podgorski / Sun-Times Media

Ald. Pat J. O’Connor talks with Ald. Leslie A. Hairston during a City Council meeting in 2014. File Photo | Al Podgorski / Sun-Times Media

“Our campaign manager likes to call it the island of misfit toys,” Vasquez said. “It’s a reflection of Chicago. It’s kind of piecemeal put together but we made sure to have one common goal and work towards it … Ald. O’Connor’s got these precinct captains that owe him favors for jobs he’s gotten them, they’re very disciplined. What they have is an operation, what we have is a movement.”

Another thread connecting the races is that both Vasquez and Calloway are being confronted with homophobic remarks they’ve made in the past.

In a comment he posted on twitter, Calloway said in part “those statements are not reflective of the man I am today, and I deeply regret them.”

Community activist William Calloway speaks to reporters. File Photo. | Ashlee Rezin/Sun-Times

Community activist William Calloway speaks to reporters last year. File Photo. | Ashlee Rezin/Sun-Times

But his campaign has refused to make Calloway available for an interview, saying instead the South Shore resident plans to host a town hall Sunday from 1-3 p.m. at the Hyatt Place Chicago-South /University Medical Center, 5225 S. Harper Ave.

Hairston’s team didn’t comment on the homophobic posts Calloway made in past Facebook posts, but the 20-year incumbent says she’s feeling good about the campaign she’s running.

 “This is about more than just getting out there and running, you have to have done something, you have to have a record,” Hairston said. “I have a record, I’ve taken the lead and hits on a lot of different things … he does what he does very well and we’re grateful for the light that was shined, but the work has to be done and it’s a lot of hard work. It’s not just about having something to chant, you have to have the capability to bring this to fruition.”

In th 40th Ward, O’Connor says that Vasquez’s record is fair game. Vasquez has apologized for the comments, old rap lyrics that O’Connor has highlighted on a web site.

“I see this as an opportunity to have a conversation about what kind of society and environment creates that kind of behavior,” Vasquez said. “At the doors, I provide the context for who I was then and apologize for the language and that it hurt people and I think neighbors see the person I am.”

40th Ward aldermanic candidate Andre Vasquez 2019 election Rich Hein

40th Ward aldermanic candidate Andre Vasquez at the Sun-Times Dec. 20. | Rich Hein/Sun-Times

 At a 40th Ward forum, the two traded barbs about those remarks and O’Connor’s role as a member of the Vrdolyak 29, a group of 29 mostly white aldermen led by former Ald. Edward Vrdolyak who opposed every policy move of then Mayor Harold Washington.

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 “He knows nothing about the timeframe,” O’Connor said. “When Harold Washington was re-elected he put me into a leadership position … Mayor Washington had dinner at my house. [Vasquez] comes from a time where if you disagree you have to hate one another — I come from a time where you can disagree but you can be friends, you can still have a dialogue and what’s what we had back then.”

West of the 40th Ward, Reboyras is fending off Jessica Gutierrez.

To her, the choice for voters is simple: “either you vote for change or you vote for 16 years of incompetence.”

 “It’s not all the time that the 30th Ward gets into a runoff — it’s been 16 years since the alderman had a challenger, a viable challenger, someone who made him get from behind his desk and knock on doors,” Jessica Gutierrez said.

From left, 30th Ward aldermanic candidate and incumbent Ariel E. Reboyras and challengers Jessica W. Gutierrez and Edgar "Edek' Esparza met with the Sun-Times Editorial Board Friday, January 4, 2019. | Rich Hein/Sun-Times

From left, 30th Ward aldermanic candidate and incumbent Ariel E. Reboyras and challengers Jessica W. Gutierrez and Edgar “Edek’ Esparza met with the Sun-Times Editorial Board Friday, January 4, 2019. | Rich Hein/Sun-Times

Reboyras credits the results of the Feb. 26 election — he finished only 27 votes ahead of  Jessica Gutierrez — to people in the ward not coming out. He’s out knocking doors to shore up support in the ward he’s lived in for 32 years.

 “I’ve spoken to over 5,000 voters over the course of this campaign and I’m … going back out there and doing it all over again,” Reboyras said. “She talks about old and new and you’re right, I’m 65, but I feel like I’m 32. I’m not ready to retire — the ward and the constituents need someone who’s been there to represent them well.”

Jessica Gutierrez counters: “We’re just saying ‘listen, it’s been 16 years, and the current alderman was incapable of garnering 50 percent plus one’ — a majority of the ward is demanding change, and that’s what we should give them.”