Taylor Faces Four Challengers in 20th Ward Race

Ald. Jeanette Taylor is seeking a third term in Chicago's 20th Ward against four challengers, all of whom live in Woodlawn.

Updated on Nov. 10, 2026 in Elections

Bold flat-color editorial illustration of a symmetrical stone civic building facade in navy and cream, evoking local municipal representation. — Ald. Jeanette Taylor faces four challengers, all Woodlawn residents, in her bid for a third term representing Chicago's 20th Ward. AI Illustration. Upload story photo >

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Do you think Ald. Jeanette Taylor deserves a third term in the 20th Ward?

Ald. Jeanette Taylor faces four challengers in her bid for a third term representing Chicago's 20th Ward. Jennifer Maddox, Andre Smith, Jarquetta Egeston and Tshey Gebre have filed to run against her.

Why it matters

The 20th Ward covers most of Woodlawn and parts of several other Chicago neighborhoods, so the outcome will shape local representation across that area. Taylor's 2023 win was narrow enough to avoid a runoff, and the candidates' petition filings are already drawing objections.

Taylor won 53% of the vote in 2023, compared with 26% for Maddox and 21% for Smith, avoiding a runoff. Whether the pending petition challenges will affect the ballot is not yet known.

The players

Jeanette Taylor

Taylor is the incumbent alderman of Chicago's 20th Ward, first elected in 2019 after the departure of Willie Cochran.

Jennifer Maddox

Maddox is a Woodlawn community figure who founded the nonprofit Future Ties in 2011 and placed second in the 2023 race.

Andre Smith

Smith founded the violence prevention group Chicago Against Violence and placed third in the 2023 race.

The details

Smith filed objections to Maddox's and Gebre's petition signatures, and Gebre challenged Smith's petitions, according to the Chicago Board of Elections. All five candidates live in Woodlawn, and Taylor was first elected in 2019 to fill the seat vacated by Willie Cochran, who pled guilty to wire fraud.

2011: Jennifer Maddox founded the nonprofit Future Ties.
2019: Taylor was first elected to City Council, filling Cochran's seat.
2023: Taylor won a second term with 53% of the vote.

Legal Context

The 20th Ward seat has changed hands since Willie Cochran pled guilty to wire fraud, which led to Taylor's first election in 2019. The current race extends that succession with a field of challengers, all drawn from Woodlawn.

Woodlawn and other 20th Ward residents will choose who represents them on the City Council. Petition objections could change which names appear on the ballot, so voters should check the final candidate list.

The takeaway

Local council seats can turn on a handful of votes and on procedural challenges, so following ballot certification matters as much as the campaigns themselves.