Leslie Hairston, a 20-year incumbent, is in a runoff against William Calloway, a community activist who has been particularly vocal about the murder of Laquan McDonald by former Chicago police officer Jason Van Dyke.
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The ward they're vying to represent, the 5th, covers parts of Hyde Park, Jackson Park and South Shore.
Calloway picked up a major endorsement Thursday from the Chicago Tribune.
"I'm the best candidate for the job because of my grassroots activism, my community organizing experience and my ability to convene people from all across the spectrum," he said. "I think it will be to Chicago Tribune readers, I think it will carry a lot of weight, but as we both know endorsements alone do not win campaigns."
Hairston hopes her lifelong roots in Hyde Park and her experience as a progressive alderman will send her back for another term. She was one of five aldermen who voted against the parking meter deal and Wednesday voted against the police academy and Lincoln Yards.
But it's the Obama Library, the major development project in her 5th Ward, that voters are focusing on.
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Calloway claims Hairston sides with the Obama Foundation and is against a community benefits agreement. Hairston says that's false.
"The foundation does not support it. That doesn't mean I don't continue to advocate for it," she said.
While Calloway supports term limits, Hairston says her City Hall experience is an asset, especially when it comes to financial issues. She points out that her opponent is being sued for back rent for his campaign office.
"This is going to be a person who is going to be making decisions about the city budget," she said. "If you can't do that for yourself, how are you going to do that with 55,000 people you represent?"