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.

State Sen. Kwame Raoul participates in a Chicago Tonight candidate forum March 12, 2018.

State Sen. Kwame Raoul has won a hard-fought race against a crowded field of eight candidates vying to be the Democratic nominee for Illinois attorney general. He will face political neophyte and former Miss America Erika Harold who won the GOP nomination.

Democratic candidates for attorney general raise their hands Monday on “Chicago Tonight” in response to Carol Marin’s question, “Should Mike Madigan step down as chairman of the Democratic Party?”

Political leaders of the fabled Chicago Democratic machine have lost public support from a group of lawyers, one of whom may in the near future be well-placed to do more than just talk about rooting out corruption.

Meet the eight Democrats running for Illinois attorney general Monday during a special hourlong episode of “Chicago Tonight.” Watch the full video.

Jesse Ruiz

A Latino attorney with connections to high-powered politicians, including Chicago Mayor Rahm Emanuel, is expected join the field of Democrats running for Illinois attorney general.

Jesse Ruiz

Former Chicago Public Schools CEO Jesse Ruiz on how the district lost its “moral high ground” because of school budget cuts.

Jesse Ruiz

Interim schools chief Jesse Ruiz joins us to discuss the financial challenges facing the Chicago Public Schools. 

Should Chicago have an elected school board? The issue separates Mayor Rahm Emanuel from his challengers. And voters from 38 wards will have a chance to weigh in on Feb. 24 when they can vote on an advisory referendum. We take a closer look.

The Chicago Board of Education plans to close 54 schools, citing a $1 billion deficit and under-enrollment. Critics say this move will disrupt communities and put kids in danger. For both sides of the debate, PBS NewsHour's Jeffrey Brown talks with School Board vice president Jesse Ruiz and Karen Lewis, president of the Chicago Teachers Union.