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A photo collage shows eight CEOs and two interim CEOs of Chicago Public Schools. Top row, from left: Janice Jackson, Forrest Claypool, Jesse Ruiz. Middle row, from left: Terry Mazany, Jean-Claude Brizard, Barbara Byrd-Bennett. Bottom row, from left: Ron Huberman, Arne Duncan, Paul Vallas. (WTTW News)

With Janice Jackson stepping down as CEO of Chicago Public Schools, Mayor Lori Lightfoot will now be on the hunt for the 10th person to head the district since the position was created in 1995. Here’s a look back at the people who’ve held the spot and where they are now.

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Former Chicago Public Schools chiefs Paul Vallas and Terry Mazany will talk with us as part of a series of discussions we are having with education experts and elected officials on the colossal challenges facing Chicago Public Schools and what it means for students and parents.

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We take a closer look at the new-look Chicago Public Schools with Andrea Zopp, a Chicago Board of Education member who voted to shutter 49 schools, the former interim CPS CEO Terry Mazany, as well as Wendy Katten of Raise Your Hand, and Jitu Brown of Journey for Justice.

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As the stalemate between the Chicago Teachers Union and the Chicago Public Schools goes into a third day, we talk with former leaders of each organization about what's at stake.