Meet Karen Calloway: Kenwood’s Golden Apple Award-Winning Principal

For Mother’s Day weekend, the Chicago Defender shares stories of dynamic Black women thriving in their careers and providing loving guidance for their families.

Kenwood Academy High School Principal Karen Calloway had yet to learn that a Friday morning event would be about her.

When she took the stage at the school’s auditorium, she planned to celebrate the success of her senior class. They were approaching $70 million in earned scholarships, a school record.

But minutes into the program, as a student was about to share her Kenwood experience at the podium, Illinois Lt. Governor Juliana Stratton and Alan Mather, president of the Golden Apple Foundation, stormed the stage. They surprised Calloway with the Stanley C. Golder Golden Apple Award for Excellence in Leadership.

The mostly packed-out auditorium of students, supporters and friends roared as their principal embraced Lt. Gov. Stratton, Mather, CPS Chief Executive Officer Pedro Martinez and Kenwood students and staff and family and friends.

A crowd of students, faculty, staff and friends gathered to cheer Kenwood Academy Principal Karen Calloway, recipient of the Golden Apple Award for Excellence in Leadership.

Even, the school’s choir and drum line, assembled upstage, erupted in song.

“Principal Calloway listens to you, she listens to faculty, she listens to staff, she listens to students, and she builds a beautiful, beautiful place for all of you to learn, to love and to grow,” said Mather as he addressed the crowd.

Calloway was selected from a pool of 130 Pre-K through 12th-grade academic leaders across Illinois. Her recognition as a Golden Apple Award for Excellence in Leadership recipient means she “had a significant and sustained positive impact on the school, created a culture of inclusivity, and delivered dramatic student growth,” according to a release by the Golden Apple Foundation.

Calloway also receives a $10,000 cash award, with $5,000 for her and the other $5,000 to Kenwood Academy for a project of her choosing.

“This was extremely kind,” said Calloway after the event. “And I really, really appreciate it. And I feel very honored and humbled to be a Stanley Golder Leadership Award recipient.”

“Mr. Golder has such an amazing vision for providing access to all students across the country,” she said. “It’s a great honor to be able to receive this award this year.”

As the recipient of the Golden Apple Award for Excellence in Leadership, Karen Calloway receives a check.

For Calloway, Friday’s surprise award was the culmination of the work she has been doing at Kenwood since she started at the high school in 2001 as a counselor. Since then she has served as the school’s counseling department chair, assistant principal and now principal.

Also, receiving this prestigious honor on Mother’s Day Weekend has a special significance for her.

“It’s exciting to know that I’ve been a mom to my own son and also to many of the students as well,” Calloway said. “So I think being celebrated on Mother’s Day and receiving this award just makes it all the more special.”

But even then, not too long after receiving her award, Calloway focused on her students, who are, in her words, “the secret sauce” of the whole deal.

“My job is to make our world better one student at a time, and believing in every student, setting high expectations for every student, and always supporting them all the way through adulthood,” she said.

What motivates her as a principal and academic leader is helping people develop and achieve personal greatness, whether it’s her students or adult colleagues. For her, it’s a reward with invaluable and substantial benefits.

“My ‘why’ is that when I leave, I want to be able to say, ‘Hey, I did my job.’ I did what I could to make our world a better place.”

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