Meet Heather Debby, Golden Apple Award Winner
13 May 2026
This well-deserved recognition honors the impact Ms. Debby has had on hundreds of students throughout her career.

Last Wednesday, Ms. Heather Debby was under the impression that she and her students had been brought to the Disney II Magnet School auditorium for an assembly about attendance. However, she suddenly heard her name being yelled from a microphone while the curtains parted to reveal her family, colleagues, and even the parents of some of her students all cheering for her on stage. Ms. Debby had won the prestigious and highly competitive Golden Apple Award for Excellence in Teaching!
As she climbed the stairs to join the celebration on the stage, Ms. Debby felt both overwhelmed and excited; buoyed by the incredible CPS communities she has encountered throughout her career. She trained at Morton Elementary School in East Garfield Park, began her career at Pablo Casals School of Excellence in Humboldt Park, and now teaches at Disney II in Independence Park. The people she met, experiences she had, and lessons she learned at each of these schools brought her to where she is today.
In fact, the community support Ms. Debby received during this process is quite literal—the steps to the stage were built by Disney II parents, students, and her husband Scott Legan, a physical education teacher at Armour Elementary in Bridgeport.
“My husband has supported me so much through my career and through this process,” said Ms. Debby. “Walking up those steps felt like such a beautiful metaphor for the way he and the DII community have held me up and built me up throughout my career here.”

This well-deserved recognition honors the immense impact Ms. Debby has had on the learning and lives of hundreds of students throughout her career. As an English Language Arts (ELA) teacher, she works with students as they learn how to comprehend difficult texts and express themselves and their ideas through writing. She describes her teaching style as relational, silly, and demanding; an approach that fosters trusting relationships and creates a safe environment for nuanced discussions about a wide variety of complex topics.
Even though Ms. Debby has now been teaching for eighteen years, she was once just starting out. Teaching is incredibly rewarding, but it can also be exhausting—especially at the start. Ms. Debby encourages new teachers to remember that this career is a marathon, not a sprint. Leaning on experienced colleagues and building up sustainable systems can help teachers stay in the classroom for the long haul.
And to her students, Ms. Debby wants to say thank you. She feels grateful to her students for all of the laughs, for challenging themselves, and for welcoming her into the DII community with open arms.
“Thank you for making my job so much fun,” she said. “You have made our classroom and community so special, and I love being your teacher.”

Watch Ms. Debby’s surprise Golden Apple Award celebration here and read the Golden Apple Foundation press release here. Learn more about the Golden Apple Foundation and see the full list of award recipients here.
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