Karen Calloway, the principal of Kenwood Academy High School, arrived at her school Friday with a plan to celebrate the senior class on their achievement of receiving a combined $67 million in scholarships this year.

But something felt off.

“I couldn’t figure it out,” Calloway told the Sun-Times later in the day.

Instead, Calloway learned she was the one being honored when she saw Alan Mather, president of the Golden Apple Foundation.

“I was shocked,” Calloway said of being presented with a prestigious Golden Apple Award for Excellence in Leadership.

The award, given to two school leaders in Illinois this year out of 130 nominations, honors “exemplary performance in school leadership by a principal,” the foundation said.

Kathleen Lopez Rodriguez from Charter Oak Primary Academy in Peoria was this year’s other recipient.

Calloway, a lifelong South Side resident, has been the principal of Kenwood Academy for five years now. She started working in education as a guidance counselor, then held several other positions before becoming an assistant principal, and finally, principal. 

“I’ve never really picked jobs,” she said. “I’ve just kind of always was invited or I fell into them because I really just wanted to work with kids.”

The Hyde Park resident plans to stay at Kenwood, where she’s worked for the last two decades.

Calloway said she never imagined she’d win an award from the Golden Apple Foundation, which is also known for giving scholarships to students who go into education.

“I never, never, never thought I’d win one,” Calloway laughed, adding that she was “humbled and extremely flattered” to be in the company of previous award winners, including a previous Kenwood Academy principal.

The award includes a $5,000 award for Calloway, as well as a $5,000 for a project for her choice that will benefit her school.

Calloway said she was considering putting the money towards helping her students with access to post-secondary education, but also noted the school’s dance studio could use a renovation.

Calloway wasn’t the only Chicago-area educator who won an award from the foundation this week. 

Latavia Hinton, an eighth grade teacher at Daniel Boone Elementary School in West Ridge, was surprised with a Golden Apple Award for Excellence in Teaching on Thursday, which comes with a $5,000 award and a spring sabbatical provided by Northwestern University.

Four other Chicago teachers received the excellence in teaching award: Rick Coppola and Helen Chan, of South Loop Elementary School; Anquineice Brown of Marquette Elementary; and Rachel Werderits of Saint Andrew School.

Mariah Rush is a staff reporter for the Chicago Sun-Times via Report for America, a not-for-profit journalism program that aims to bolster the paper’s coverage of communities on the South Side and West Side.