Joyce Kenner, CPS’ most prominent principal, to retire after 3 decades at Whitney Young

Joyce Kenner, one of the longest-tenured Chicago Public Schools principals, who has led the highly selective and prestigious Whitney Young Magnet High School through academic and athletic success along with several controversies over a nearly three-decade run as principal, is retiring at the end of the school year, she announced Wednesday.

Kenner, 65, has become synonymous with Whitney Young over the years, through both ups and downs and eight permanent CPS CEOs — plus a few interim. She has been a vocal administrator among many afraid to speak against their bosses, while also a target of criticism that she hasn’t always handled student concerns with care.

“I have great anxiety, because this has been my life,” Kenner told the Chicago Sun-Times in an interview this week. “Almost half my life I’ve spent at Whitney Young.

“I’m nervous about the next stage of my life. This has been a dream job for any educator.”

Keith Hale/Sun-Times file photos

Kenner, only the third principal in Whitney Young’s 47-year history, still had her sights set on bigger dreams, though. She told the Sun-Times in a 2011 interview that she wanted to be CEO of the district.

The principal of course never was tapped for that position in the 11 years since. But she confirmed she expressed interest to city leaders when Janice Jackson stepped down last year. And as she heads toward retirement, her feelings about the top job haven’t changed.

“I believe that I would’ve been an exceptional CEO, and one of the reasons is because I’ve been in the trenches,” she said.

A Dayton, Ohio, native, Kenner holds degrees from Ohio University and Loyola University. She studied physical education, and started her Chicago career working for the Rev. Jesse Jackson’s Operation PUSH as the organization’s deputy education director before she moved to CPS. Kenner’s 27 years leading Whitney Young make her the longest-serving active CPS principal at a single school.

Troy LaRaviere, president of the Chicago Principals and Administrators Association, said “every principal in CPS has detractors,” but Kenner has been an inspiration to colleagues and “her school’s performance speaks for itself.”

“Joyce has been a dedicated CPAA member since 1996 and we are indebted to her and the example she has set for all of us,” he said.

Kenner said the pandemic had no bearing on her decision to retire. She wants to spend more time with her 3-year-old granddaughter and soon-to-be-born grandson. And she plans to spend a year finishing a book about how she handled various scandals as a principal before touring the country to advise administrators on school leadership.

One thing is clear — there was no shortage of controversies in her 32 years at Whitney Young, the first five as an assistant principal and the rest as principal.

John H. White/Sun-Times file photos

Kenner’s first dustup at the Near West Side high school came nearly 26 years ago in her first spring as principal. Students working on the school newspaper accused her of censorship in May 1996 when she seized all 2,000 copies of their latest issue. She blamed a derogatory comment printed about a teacher, while some students suspected she was trying to hide a letter to the editor from a member of Whitney Young’s LGBTQ pride club.

Kenner’s most significant trouble was in 2011 when she was among the schools officials subpoenaed for records in a federal criminal investigation of the district’s enrollment practices at selective high schools. Kenner testified before a grand jury about so-called “principal picks,” an often-clouted process in which a certain percentage of kids at the test-in schools were handpicked by principals. Two aldermen were found to have lobbied Kenner to accept their kids, and the CPS inspector general at the time recommended banning her for life from that process. Kenner said at the time she followed the system that was in place, and all but one of her picks in 16 years had graduated.

In the past decade, Kenner has faced a petition calling for her resignation during the racial justice protests of summer 2020; was warned and then suspended for repeated poor oversight of a swim coach’s off-the-books pool rental scheme; and came under fire for her handling of students’ misconduct allegations against a track coach who wasn’t suspended until a Sun-Times report last year. That latest controversy came as Kenner submitted her name for consideration for CEO.

“Everybody has regrets,” Kenner said. “I regret some of the ways I handled certain situations. I eventually got it corrected. But if I had addressed it differently at the beginning, maybe the outcome would’ve been different. But one thing that makes a great leader, to me, is recognizing you made a mistake, telling your community, ‘My bad, I made a mistake, I’m going to correct it, and let’s move forward.’

“If people look at the work that I have done across these 32 years, there’s no doubt that I’ve made a difference in people’s lives.”

Despite those challenges, she also oversaw great successes. Kenner, a former college cheerleader, prides herself on prioritizing athletics and clubs along with academics to help students build well-rounded college profiles, offering over 100 clubs and activities and 19 sports. The school has won championships in basketball, chess, the academic decathlon, golf, swimming, tennis and more. The school’s band, orchestra and choir programs have earned top state honors.

Kenner credited her students, “exceptional” assistant principals and “phenomenal” teachers and support staff for those triumphs.

“I’ve always wanted my legacy to be academics plus extracurricular activities equals success,” Kenner said. “You just cannot have the academics without the other.”

Kenner also oversaw the naming of the school’s new athletic complex after alumna Michelle Obama in 2019. The former first lady was one of several accomplished guests she hosted at the school over the years for student discussions, along with Mark Cuban, Venus and Serena Williams and more.

“We extend best wishes and gratitude to Dr. Joyce Kenner as she announces her pending retirement in her 27th year as principal of Whitney Young High School,” CPS spokeswoman Mary Fergus said. “Her steadfast leadership and many long-term contributions inspired countless students and staff members.”