Middle school teacher at ‘exemplary’ Chicago school honored with $25,000 prize

An adult female with long black hair and wearing an orange suit jacket sits between a crowd of students smiling for the camera.
Comfort Agboola accepts the Milken Educator Award on Fri., Feb. 2, 2024 at Poe Classical Elementary School in Chicago, Illinois. Agboola teaches grades 6th through 8th. (Crystal Paul for Chalkbeat)

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Comfort Agboola was thinking about her upcoming math lesson while keeping an eye on her middle school students during an assembly this morning to celebrate her school’s recent achievement as one of only five majority-Black Chicago schools to earn an “Exemplary” designation from the state.

At least that’s what she thought the assembly was about.

Until one of the visitors at the assembly turned to announce a $25,000 award to one of Poe Classical Elementary School’s teachers. It was Agboola.

The gym erupted in applause and cheers as Poe students waved light blue Poe Classical flags and paper signs with Agboola’s face on them. The glittering Poe cheer team burst into dance, and colleagues rushed to hug a stunned Agboola.

The event brought out some special guests – including Congresswoman Robin Kelly, State Superintendent of Education Tony Sanders, and Chicago Public Schools Chief Executive Officer Pedro Martinez – to the selective enrollment school in the city’s Pullman neighborhood.

Jane Foley, the senior vice president of the Milken Educator Awards, announced the award, which is given to up to 75 educators across the U.S.

Agboola is the only Illinois educator to receive the award this year and the first Chicago Public Schools district teacher to receive the award since 2010.

The Milken Educator Award was created by Lowell Milken in 1987 to honor early- to mid-career education professionals based on their achievements and “the promise of what they will accomplish,” according to a press release from the Milken Family Foundation.

“I was just in shock,” Agboola said afterward. “It pushes me to do more in the classroom.”

Martinez said in a statement that “exceptional efforts” for Agboola’s students “exhibit what we as a District can accomplish if we continue to focus on core instruction and welcoming, supportive school communities.”

Along with the cash award, honorees attend an all-expenses-paid forum with Milken in Los Angeles, receive mentorship opportunities, and become lifetime members of the Milken Educator Network, a nationwide group of educators and education professionals including past award recipients.

“They never let you go,” said Mark Jordan, who won the award in 1989 when he taught music at Gompers Fine Arts Option School in Chicago.

“It’s the Oscars of education. I don’t see anyone saying I do it for the accolades,” he said after helping to present the award to Agboola Friday. “So, if I see another educator being honored, I want to be there.”

The $25,000 award is unrestricted, and recipients have used the money in diverse ways, including spending funds on their children’s or their own education, establishing scholarships, or taking a dream vacation, according to the press release.

Agboola teaches reading, English language arts, and math at Poe. Her passion, however, is writing, and she brings that passion into the class. In her classroom, for example, students have a living room, library, and publishing area where they can practice spelling and respond to writing prompts on a collection of typewriters, while also learning about typewriter mechanics.

Outside of the classroom, Agboola extends student learning with opportunities like spelling bees, a podcast club, debate, and Model UN. She has earned several other distinctions including a Pulitzer Center Teacher Fellowship, the 2020-21 Network 13 Teacher of the Year Award, and the State of Illinois’ 2023 Meritorious Service Award in the Teacher Category.

“I like her teaching style,” said Jayson Ridgell, one of Agboola’s sixth grade students. “She doesn’t yell and she’s patient.”

He said Ms. A, as her students call her, visits every table in the classroom to work with individual students.

Agboola joined Poe in 2020 during the pandemic and spent her first year there teaching virtually, but that wasn’t the first challenge she’s faced in her teaching career.

In her first teaching job at the now-closed St. Hyacinth Basilica School in Avondale more than a decade ago, she worked with a young student who was non-verbal. When the student spoke for the first time in Agboola’s presence, she knew teaching was her calling - just as it was her mother’s.

“Parents are sending their most valuable thing to us,” she said. “I know that anything they do they are still growing and learning. They need our support.”

When the celebration waned and most students returned to their classes, Agboola remained surrounded by cameras as she called another important educator in her life: her mother.

“I just want to thank you too, mom,” she said over the phone. “Because you inspired me in your career as an educator.”

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