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Pittsboro Elementary School teacher wins national ‘Oscars of Teaching’ award

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Shane Henderson receives a $25,000 check as a winner of the Milken Educator Award. Courtesy of Milken Family Foundation

Shane Henderson, a fourth grade teacher at Pittsboro Elementary School, received the Milken Educator Award, a national award known as the “Oscars of Teaching,” on Wednesday morning, according to a press release from the Milken Family Foundation. 

The award, presented by the Milken Family Foundation since 1987, recognizes early- to mid-career educators “furthering excellence in education” across the country and gives winners an unrestricted $25,000 cash prize, the release says.

“Shane Henderson’s work models best practices in instructional leadership, peer mentoring, and professional collaboration, making him a standout educator and model for the profession,” said Milken Educator Awards Vice President Stephanie Bishop, a 2001 Virginia Milken Educator herself. “Welcome to the Milken Educator Network, Shane! We’re thrilled to have you join this prestigious community of educators.” 

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Henderson, a product of Chatham County, is the only recipient from North Carolina for the 2025-26 award cycle, which will recognize 30 educators nationwide. He is the state’s 58th recipient since North Carolina joined the Milken Educator Awards program in 1994, per the release. Overall, the Milken Educator Network includes more than 3,000 education professionals nationwide.

By the end of this cycle, the awards program will have invested more than $76 million in individual financial prizes and more than $146 million in the national network, according to the press release.

Bishop surprised Henderson with the award during a schoolwide assembly honoring Pittsboro Elementary School’s 65th anniversary in the school gym, according to a release from Chatham County Schools, along with state Superintendent Maurice “Mo” Green.

Green said Henderson received the award thanks to his commitment and passion for student success.

“He keeps students at the heart of his work, creating inclusive learning environments to support all students along their educational journey,” Green said. “Mr. Henderson is a wonderful example of why we need to revere educators — his selfless dedication has shaped the future of our state.”

Shane Henderson is congratulated by North Carolina State Superintendent of Public Instruction Maurice ‘Mo’ Green. Courtesy of Milken Family Foundation

Dr. Anthony D. Jackson, superintendent of Chatham County Schools, said the award is not just an honor for Henderson, but is also a reflection of the district’s mission for excellence.

“It affirms our mission of ONE Chatham for ALL students by highlighting the transformative impact that passionate, dedicated educators have on every learner they serve,” Jackson said in the district release.

Henderson “has become a beloved teacher over the past decade,” the foundation’s press release said, moving from bus driver, to instructional assistant, to classroom educator. He still has his commercial driver’s license so that he can step in as a bus driver when needed.

Recently, his fourth grade class recently saw a 16-point increase in reading proficiency and an overall passing rate of 75% on end-of-year assessments. 

But his win was also tied to the work he does outside the classroom. He meets with parents to set goals for students and celebrate academic achievements throughout the school year. As a grade-level chair, he also mentors fellow educators who can support younger classrooms. He runs a “Breakfast for Brainiacs” club for fourth graders, represents his colleagues on both the School Improvement Team and the behavior team, and has led a running club at the school.

Shane Henderson poses with his fourth grade class after winning the Milken Educator Award. Courtesy of Milken Family Foundation

His reach also extended beyond the school when he shared research-backed strategies to improve reading outcomes at the National School Boards Association’s Conference for Public Education Leaders. 

Henderson will attend the Milken Educator Awards Forum in Washington, D.C., in June to meet fellow winners and education leaders. He also gets access to mentorship opportunities with veteran winners of the award. 

“Outstanding educators like Henderson are not aware of their candidacy for the Award,” according to a press release from the Department of Public Instruction. “Recipients are sought out while early to mid-career for what they have achieved — and for the promise of what they will accomplish given the resources and opportunities afforded by the Award.”

You can read more about Henderson and the award on the foundation’s website.