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.

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. 

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. 

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.

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.