Ald. Jeanette Taylor aims to fend off rivals to her 20th Ward seat, where persistent challenges abound

Four years ago, community activists Jeanette Taylor, Jennifer Maddox and Andre Smith were among a crowded field of candidates vying for the 20th Ward City Council seat, which was vacant following a string of corruption scandals.

Now the three are in a rematch for the position. Only this time, Taylor — who easily topped the first-round vote in 2019 and went on to win the seat — brings the benefits of incumbency but also a record to defend.

Taylor took over the position from former Ald. Willie Cochran, who was indicted on corruption charges and pleaded guilty to wire fraud in federal court. Taylor had become known for her activism in the community, like participating in a 34-day hunger strike that led to the reopening of the Dyett High School campus in Washington Park as well as $14.6 million in upgrades and encouraged the University of Chicago to open an adult trauma center.

Since taking office, she has helped secure a 2020 deal with the city to ensure more affordable housing near the Obama Presidential Center and let people who live nearby benefit from its creation. Taylor tweeted about her own journey with affordable housing in the city after she got a letter from the Chicago Housing Authority that said she could apply for a housing choice voucher — almost 20 years after she joined the waitlist in 1993, when she and her three kids shared a one-bedroom apartment with her mother, sister and her sister’s child.

Taylor served as a Local School Council representative from 1993 to 2016, according to her 2023 candidate questionnaire. She graduated from Dunbar Vocational High School, then Dawson Technical Institute.

She wrote that the most pressing issue in the South Side ward — one long troubled by poverty and crime — is “stable and affordable housing” and said she continues to hold the CHA accountable because “affordable, safe and secure housing contributes to the overall public safety in communities in my ward.”

She said she believes another four years for her will mean continued improvement of housing, schools, businesses and public safety in Chicago.

“As alderwoman, my work is informed by the constituents in my ward,” she wrote. “My work centers around what the community wants and needs. I have spent my entire adult life in service to my community and I have kept every promise that I have made to my constituents.”

She also wrote that she believes the best solution to strengthen public safety in the city “is to invest in Chicago’s neighborhoods equitably.”

At the end of 2022, Taylor had almost $48,000 for her campaign, according to financial statements. She started the fourth quarter with around $8,000 and garnered over $70,000 during the last three months of the year, much of which came from SEIU Healthcare PAC and the SEIU Illinois Council PAC Fund as well as the Cook County College Teachers Union. Her largest and most consistent expenditures were on staff salaries during this time.

In the new year, she has received $35,000 so far from the Chicago Teachers Union PAC, along with some donations from other labor unions.

Recently, Taylor has raised her voice on a couple of major projects taking place in the ward, including the expansion plans for the 47th Street intermodal rail yard and the city’s controversial plan to shelter migrants at the old Wadsworth Elementary School in Woodlawn. Taylor complained that the city was uncommunicative with the community about its plans — something Mayor Lori Lightfoot disputed. On the rail yard expansion, which required the purchase and razing of scores of homes in the area, Taylor vacillated on her position, prompting a delay in a recent, key City Council vote on the project, but ultimately voted in favor of it because of promised community benefits.

Smith and Maddox have also lent their time and voices toward the subject of the Woodlawn shelter. Smith was seen earlier this month wearing a neon yellow vest and getting in front of a CTA bus carrying migrants, in an attempt to stop the bus from entering the shelter’s parking lot, while Maddox has attended and spoken at community meetings on the matter.

“I decided since the city wasn’t listening to us saying we didn’t want them there, and the alderwoman wasn’t being honest with us, I decided to protest and stand in front of the bus and not let the migrants go into that shelter with our tax dollars,” said Smith, who also ran for the seat in 2015 and made a run for Cook County commissioner in last year’s Democratic primary.

He currently works as a finance manager but said he plans to take on aldermanic responsibilities full-time if elected. He previously owned a number of beauty and barber shops around the city, including a few in the 20th Ward, he said.

Smith said he was born in Woodlawn and has lived in the 20th Ward most of his life. He has one daughter and four sons, he said.

He said he spent decades “fighting to better our city and our ward,” but even after protesting and marching, he said he realized the only way to make a difference the way he wanted to was to get a seat at the table.

“I want change for the community,” Smith said. “We need somebody that cares about our community. We need real leadership. The 20th Ward is struggling.”

He said he feels he’s gained momentum by “knocking on doors and shaking hands” and showing the community that he is willing to show up for them. He said he’s “never needed a lot of money like other candidates” for campaigning because he is out every day “doing the work” himself.

“I’ve been out,” he said. “People know me. People are excited that a change is coming.”

The top issue in the ward currently is the city’s investments toward the shelter for migrants in Woodlawn, he said, which is “unfair to residents, the taxpayers” because of homelessness he sees in the area already. High property taxes plaguing residents, he said, is a close second.

Maddox recently retired from the Chicago Police Department after more than a quarter century as a police officer. She runs Future Ties, a nonprofit in the Woodlawn area aimed at supporting and serving local youths. She also currently sits on the Local School Council of John Fiske Elementary School and is an “active participant” in a number of other community-based organizations, she said.

She said she was born and raised on the South Side and attended Corliss High School. She earned a bachelor’s degree in criminal justice from the University of Illinois and has a master’s degree in business administration from Xavier University. She said she has two sons and three grandchildren.

Maddox said she knew she wanted to run for alderman again because she’s “been in the ward a long time” and has seen all of the aldermen who’ve come and gone look at “the ward as a whole” but not “connecting the dots as far as one side of the ward to the other.”

“People don’t know what one side of the ward is going versus the other side,” she said. “There aren’t community meetings where we are tying the entire ward together. You have community meetings in Woodlawn, maybe in Washington Park, maybe in Greater Grand Crossing, but we need to bring all of the 20th Ward together at the table so one side or one community is collaborating with the other, so it can be a stronger ward where you have different entities supporting and helping each other instead of seeming like the haves and the have-nots or the one side getting something the other doesn’t. People shouldn’t feel as though they’re not included in what’s going on in the 20th Ward as a whole. They always seem to think that one community is represented more so than the other.”

The biggest items she wants to work on in the 20th Ward, she said, are public safety and bridging the gap between parents and their children’s schools.

She said her many connections within the Police Department will allow her to better tackle safety in the community, especially when it comes to helping residents understand policies and policing better. She said she wants to help the community connect with the police in a positive way “so that people feel like building relationships with the police is a necessity and are willing to do so if they understand that the police is part of the community and not have an us-against-them mentality.”

In order for children to get the best education they need, Maddox said she wants to have parents become more involved and engaged by building up parent advisory groups or Local School Councils because “parents support and input in important.”

According to Maddox’s campaign finance reports, she ended 2022 with a little more than $5,000, the majority of which came in during the same quarter.