When Lori Torres Whitt saw how the 36th Ward was oddly redrawn to include more than a handful of communities in a strip stretching about eight miles from West Town to Montclare, it pushed her to take the plunge and run for office for the city council.

“If you sit in office and represent the people here, how do you allow this to happen?” Torres asked Whitt. “And if you let this happen, what else are you letting happen?”

Torres Whitt, 49, of West Town, is challenging Ald. Gilbert “Gil” Villegas, 52, of Dunning, who is seeking a third term on the city council. They were thrown into a run-off on April 4 after neither managed to secure a majority of the vote in February.

Villegas received around 46% of the vote in the February 28 election, Torres Whitt around 30%.

In total, more than 57,000 Chicago residents live in the 36th Ward, and a majority — nearly 56% — identify as Latino, according to city data. Fewer than 10,000 voters cast ballots during the February 28 election.

The newly redrawn ward stretches from Sayre Avenue in the Northwest Side’s Montclare neighborhood across parts of the West Side to Wood Street in West Town. Along the way, the department that was described as a “pool noodle” picks up parts of Ukrainian Village, Humboldt Park, Dunning and Belmont Cragin.

The houses it contains vary from bungalows with front lawns to multi-storey buildings. Some streets are lined with Ukrainian flags, while other residents fly Puerto Rican flags.

Villegas was first elected in 2015, and he served at one point as Mayor Lori Lightfoot’s council leader. He is also chairman of the chamber’s Latino Caucus. Last year he ran unsuccessfully for Congress.

Anthony Vazquez/Sun-Times

Villegas touts his experience in government as one of the reasons why voters should give him another term, pointing out that City Hall will be in a state of transition.

“We want to make sure we have a city council and members who are experienced,” he said. “We cannot afford training at work. I want to make sure that the work I have done so far continues.”

“I do the work”

Torres Whitt is a teacher at Monroe Elementary School and she is also part of the Chicago Teachers Union executive board. The union endorsed Torres Whitt, and the CTU Local 1 PAC is one of the largest financial contributors, according to Reform for Illinois.

Torres Whitt argues that her experience as an educator, community organizer and labor lawyer prepared her for the job.

“If you want someone who is looking to make progress in the 36th Ward and in Chicago, it’s me,” she said. “I don’t claim to be progressive, I am because I do the work.”

Villegas said he will not support a candidate for mayor. Torres Whitt supports Cook County Commissioner Brandon Johnson.

Anthony Vazquez/Sun-Times

Torres Whitt and Villegas share some common traits.

Villegas also objected to how the department was redrawn, saying it resembled a “snake”, which he said at the time was appropriate because his colleagues who drew it were “self-portraits of snakes”, stabbing him in the back.

“The redistricting process is very contentious,” Villegas said during a recent interview. “But nevertheless, at the end of the day, I got an opportunity to represent the 36th Ward, I’m picking up new residents. And the fun part is, I’m originally from West Town, so this is basically just bringing me back to where I started.”

Both said more branch offices will be needed to accommodate residents living on opposite ends. Villegas and Torres Whitt support the city council – rather than the mayor – appointing committee chairs.

The two also agree on efforts like Bring Chicago Home, which aims to increase the tax on the sale of properties of $1 million or more to generate funds for services for the homeless population.

The candidates differ on issues such as policing. Villegas said he supports reopening the old Wood Street District police station or using the facility as a satellite office. The property is on the border of the 36th ward, but is within the 1st ward.

“There is a correlation between the closing of this police district a decade ago and the increase in crime in the West Town, East Town, Ukrainian Village area,” Villegas said.

Torres Whitt sees a connection between the closed city’s mental health facilities and crime. She said she is in favor of investing in mental health programs and those aimed at youth.

“We live in Chicago that invests heavily in security, and yet no one feels safe,” she said. “Let’s add the tools that officers need so they can do the job they’re trained to do.”

“It’s grass, it’s curbs, it’s pavement”

Voters have their own concerns.

Belmont Cragin resident Angel Roque said he wants to see better communication and improvements on infrastructure projects. He points to an area in front of his detached house where the grass was torn up to make way for meters.

“There’s grass, there’s curbs, there’s pavement,” said Roque, 49, who was unsure of his voice. “We can only do so much to try to improve our neighborhood, make it look better. But the other part seems to be a forgotten area.”

In Montclare, Tomas Lozada, 90, said he planned to support Villegas for another term and wants more activities for military veterans like himself. He recently moved in with his grandson after having to leave his senior home because of the conditions.

His granddaughter, Irma Cornier, 45, was unsure, but she would also like to see improvements around her neighborhood, pointing out potholes in a nearby park.

“How can such basic things not be fixed,” asked Cornier, who ran for another ward’s council seat eight years ago.

Cornier would also like to see more programs for veterans and a way to commemorate his grandfather’s 65th Infantry Regiment, a major branch of Puerto Rican soldiers.

At the other end of the 36th Ward in West Town, Zia Nix, 39, said she supports Torres Whitt because her politics align with hers. She would like to see more social services address mental health and poverty.

But she is also worried about redistricting that put her in the 36th ward.

“Can they solve these problems?” Nix asked as she walked her dogs, Burnham and Basil. “It just seems like the way they’re being redrawn isn’t really to our advantage.”

Elvia Malagón’s reporting on social justice and income inequality is made possible by a grant from the Chicago Community Trust.