Shaped like a playground seesaw, new 36th Ward brings three challengers looking to knock off incumbent

The new 36th Ward is arguably the most gerrymandered in Chicago. Stretching diagonally from West Town to the Far Northwest Side, it runs slender in the middle and expands out at each end. It resembles a playground seesaw, while others have described it as a “pool noodle” or a “waterslide.”

How it came to be shaped this way has never been fully explained, though it shouldn’t be a surprise there might have been some political retribution at play. The ward’s incumbent alderman, Gilbert Villegas, chaired the City Council’s Latino Caucus that opposed the map, which was favored by most of the council’s Black Caucus.

Regardless, the result is a contentious race in the newly drawn ward in which three residents are challenging Villegas and accusing the two-term alderman of not being familiar with the new ward’s neighborhoods and not working well with law enforcement to cut down on crime. Villegas is facing challenges from Jacqueline “Jackie” Baez, financial consultant David Herrera and Chicago Public Schools teacher Leonor “Lori” Torres Whitt.

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Nearly a year after he lost a bid to be elected to Congress, Villegas says he deserves a third term, even if it is to represent new neighborhoods. He said he has eight years on the council and a vision for the ward.

“This campaign is going to be an indication of whether or not people want experience, leadership, proven leadership, or they want to have on-the-job training,” Villegas said. “I can tell you that right now. The city is at a crossroads. And we can’t afford on-the-job training.”

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The Feb. 28 election is the first since each of the city’s 50 wards were remapped as part of the once-per-decade redrawing of political boundaries following a federal census.

Although every ward changed somewhat, the redrawing of the 36th appears to be the most radical, other than possibly the moving of the 34th Ward from the Far South Side to the downtown and Near West Side area. In that case, Ald. Carrie Austin, 34th, isn’t running for reelection following her federal criminal indictment.

The result for the 36th Ward is that about half of the current constituents of the ward are being redistricted to neighboring wards. Villegas said he is still hopeful he can avoid a runoff. If no candidate wins more than 50% of the vote in the Feb. 28 election, the top two vote-getters will compete in a runoff on April 4.

After the new ward boundaries were released, Villegas opened up what he called a “satellite office” in West Town, one of the new 36th Ward neighborhoods. He said he opened the office to help residents with city services so neighborhood residents “didn’t feel disenfranchised or disconnected.”

[ ‘Insane.’ ‘Obviously wrong.’ ‘Not a good thing.’ The new 36th Ward would stretch from the Far Northwest Side to West Town, baffling its future residents. ]

But some of Villegas’ opponents say the move to open the office was made more for political reasons since many of the residents in West Town don’t know anything about Villegas even though his name will be on the ballot in less than a week.

“Why doesn’t he open up on office on the South Side? He can be the alderman for all,” Herrera said. “The city should give all candidates the same resources to level the playing field.”

Villegas defended having the office outside of his current ward, saying “there’s nothing wrong with helping people out.”

Herrera, a native of West Town, said that the new map favors a 36th Ward candidate from West Town because there is a larger constituency in that neighborhood than the Montclare neighborhood that is Villegas’ base.

“The thing is, the incumbent lives 8 miles away,” Herrera said. “So I would almost call this an open seat. It just has an incumbent’s name attached to it. And, hands down, I know this area better than any of the competition.”

When West Town was in the 26th Ward in 2019, Herrera ran for the seat but came in last, a loss he attributed to being “drowned out” by better-funded candidates.

Fundraising is differentiating the candidates in this race as well.

Villegas had more than $79,000 on hand to start the year and raised more than $100,000 since. Torres Whitt, who is backed by the Chicago Teachers Union, had nearly $60,000 on hand at the start of the year but hasn’t raised as much as Villegas since. Baez hasn’t raised much at all while Herrera’s campaign is mostly self-funded.

Still, Herrera said he thinks it will help that he’s been involved with neighborhood groups such as the Ukrainian Village Neighborhood Association and the East Village Association, as well as attending CAPS meetings for the 12th and 14th police districts.

As it has in many aldermanic races, crime has become a focal point in the 36th Ward.

Carjackings and robberies in the ward’s new boundaries have been on the rise since 2019. To address that, Herrera wants to hire more police and reopen the former 13th police district in West Town. The district was consolidated with the 12th police district in 2012 when Mayor Rahm Emanuel closed it and two other districts to save money.

Herrera also has proposed hiring private security, an-often controversial practice.

“I hate to say it, (private security is) going to have to start patrolling the neighborhood.” Herrera said while acknowledging the idea might not be so popular. “It’s not the number one option, but at the end of the day, public safety is part of the job description.”

Villegas said he is working on having a referendum question on the ballot in 2024 to let voters determine if they want to reopen the 13th police district. He said he is doing it to put pressure on the mayor’s office to have a police district in West Town.

Torres Whitt has a different take on addressing crime. She said she wants to see an investment in the mental health institutions that were shut down during Mayor Emanuel’s tenure.

“You’re hearing mayoral candidates, and even some of my opponents, say that they want to hire (more police). But we have to recognize the conditions in which we really started,” she said.

Torres Whitt said she plans to use her seat on the City Council to create a “moral document” that can allocate money to mental health, public transportation and get quicker city services to constituents.

Torres Whitt said her 23-year career as a teacher, the last 18 at James Monroe Elementary School, is what shaped her into the candidate she is today.

“The reality is that, in my teaching, I became an advocate. I became an advocate for students and their families. And that advocacy led me to community work. I’m a community advocate, community activist,” she said.

As candidates have debated crime, Villegas’ relationship with law enforcement also has become an issue. Several of his opponents criticized Villegas’ response to unrest that occurred in the city following the murder of George Floyd, a Black man in Minneapolis, at the hands of a white police officer.

On the Northwest Side, looting occurred around the Brickyard Mall and amid the violence a man punched a police officer. Also, a woman who was visiting the mall was dragged from her car by police. The woman and companions later received a $1.7 million settlement from the city.

Baez said Villegas was too “quick to condemn the police” because he requested investigations by the Civilian Office of Police Accountability about the Brickyard incidents.

But Villegas defended his relationship with the police, saying he has the endorsement of the Chicago Police Sergeants’ Association. The Fraternal Order of Police Lodge 7, which is Chicago’s largest police union and backing Paul Vallas for mayor, has not endorsed any candidate in the 36th Ward race.

The bickering between Villegas and Baez has been consistent throughout the campaign. Baez said she supported Villegas’ campaign in 2015 and spoke to him about getting a cultural center opened for young people but that he never kept his promises. Villegas said he never committed to building the center.

Villegas also has discussed troubles Baez has had in the past, including a dispute she got involved in when she was head of the Puerto Rican Cultural Association of Chicago in 2017.

The organization was sued by a Carol Stream tent company, which claimed in a lawsuit that Baez wrote a bad check after the company provided equipment for the association’s festival. Earlier this week, Baez was arrested by Chicago Police on a warrant from DuPage County stemming from the lawsuit, a spokesperson with the Chicago Police Department said Wednesday.

Baez previously told the Tribune she wrote a check to the tent company but then canceled it after the association’s board voted not to pay the firm because the tent company did not keep up with the festival’s schedule.

Torres Whitt, meanwhile, has tried to present herself as the progressive alternative to Villegas.

She has been endorsed by Cook County Commissioner and mayoral challenger Brandon Johnson, who also is backed by CTU, as well as U.S. Rep. Delia Ramirez, who defeated Villegas last year for Congress. Torres Whitt also is backed by the progressive organization United Working Families, which is closely aligned with CTU.

Villegas said he still sees himself as a progressive in the race. He noted that last year he introduced an ordinance that would set up a Basic Income pilot program. His proposal was not passed, but a similar one did under Mayor Lori Lightfoot, who had named Villegas her floor leader in 2019. He resigned the post in 2021.

“The reality is that you just got to take a look at my track record and you can see that I’ve done the most progressive things in the City Council, so they can label whatever, however they want,” Villegas said.

rrequena@chicagotribune.com