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In Conversation: Aaron Cynic Discusses Race For Next Chicago Mayor

Listen to the conversation with journalist Aaron Cynic by clicking the below player:

Shadowproof launched a six-part series by Aaron Cynic on the upcoming mayoral election in Chicago. It presents a major opportunity to advance a progressive agenda in the city because Mayor Rahm Emanuel is not seeking a third term.

Aaron produced the first piece in the series in December. It offers an overview of what life has been like for organizers, marginalized groups, and communities facing disinvestment during Emanuel’s administration.

The next four pieces in the series will examine various issues, which grassroots groups believe the next Chicago mayor must address and answer for if they are elected.

Kevin Gosztola, managing editor of Shadowproof, was joined by Aaron for this first episode in a limited podcast series from Shadowproof called “#ChiMayor19.”

During the episode, they discuss what Rahm Emanuel’s administration was like the past eight years.

Aaron highlights the case of Laquan McDonald, a black 17 year-old who was shot and killed by Jason Van Dyke, a white police officer. Van Dyke was convicted of second-degree murder and 16 counts of assault for every shot he fired into McDonald’s body.

Emanuel initially covered up video of the shooting until a court ordered the city to release it. It was a defining moment in his administration.

If you enjoy the conversation and appreciate Aaron’s work, we could really use your support raising funds to pay for this series. Please donate here.

During the conversation, Kevin and Aaron introduce seven of the candidates to people who may not be familiar with who is running for mayor—Garry McCarthy, Bill Daley, Gery Chico, Amara Enyia, Paul Vallas, Susana Mendoza, and Toni Preckwinkle.

Aaron also highlights the indictment of Alderman Ed Burke, who has been a fixture of corruption in Chicago politics for decades. Both Mendoza and Preckwinkle have histories with this political boss.

“People in marginalized communities and people in working communities, working class folks, I think have suffered greatly here during Emanuel’s tenure and a lot of that has been due to his penchant for essentially privatizing everything and taking resources out of underfunded and struggling communities and shipping them all downtown to the Loop, to the city center,” Aaron contends.

He says, “The Laquan McDonald case was another example of how there is nearly zero police accountability in this city.” And notes, “This came on the heels of Michael Brown [who was killed by Officer Darren Wilson] in Ferguson. Laquan McDonald was essentially our Michael Brown, that was our Ferguson, that was our hands up, don’t shoot.”

Susana Mendoza and Toni Preckwinkle are the two front runners for mayor. They are both women of color, which may make Chicagoans happy because they can vote for someone who is not a white male. But neither announced their campaigns until Emanuel said he would not seek re-election.

Mendoza “won her first seat in the state legislature with the help of Ed Burke, who is now being indicted for extortion,” Aaron adds. She mentioned Burke was her mentor earlier in the election, and “once the FBI raided his offices, all of that stuff disappeared really quickly.” There are also people in her campaign that worked for Emanuel.

The Chicago Teachers Union and multiple local SEIU chapters endorsed Preckwinkle. She has been in Chicago politics, in county politics for a very long time.

“Labor is not going to endorse somebody if they don’t think they have a shot at winning. And so I think that’s why you saw those endorsements. She’s a person who I think they have worked with in the past,” Aaron suggest.

However, she has connections to Burke. She put forward several petition challenges to knock candidates of the ballot. “Those are all things that are your typical sort of Chicago machine politics.”

You can listen to the conversation by clicking the above player. And please donate if you support Aaron Cynic’s journalist effort to amplify grassroots perspectives during Chicago’s 2019 mayoral election.



Shadowproof is a press organization driven to expose systemic abuses of power in business and government while at the same time developing a model for independent journalism that supports a diverse range of young freelance writers and contributors. It is intrinsically committed to elevating voices from marginalized communities, as well as dissenting perspectives which deserve greater attention.