Diman Principal Rebello gets to walk the red carpet in Los Angeles after winning educator award

Santa Monica, Calif.,/Fall River/Somerset/Swansea/Westport Mass.— The Class of 2023 Milken Educator Award recipients were greeted by public fanfare as they touched down in Southern California last week for a national forum held at UCLA June 5-7. Hailing from across the country, these educators gathered for the first time to walk the red-carpet, participate in professional development opportunities, and to “Celebrate, Elevate and Activate” the American K-12 teaching profession.

Following their surprise notifications in October 2023 Massachusetts recipients Diman’s Andrew Rebello and Shelley Terry received their unrestricted $25,000 cash prizes from Milken Educator Awards Founder Lowell Milken and Milken Family Foundation Co-Founder and President Mike Milken.

“We are gathered to celebrate the achievements of 2023’s Milken Educators – those who have harnessed the potential to effect significant change and inspire their students to positively impact the course of our nation and the world,” said Lowell Milken. “Through the Milken Educator Award, we celebrate their achievements, elevate their practice with powerful professional development opportunities, and activate their capacity to make an indelible mark on the profession at large. We hope they will inspire many other talented young people to follow their lead and become teachers, administrators and specialists committed to blazing a path for future generations.”

This year’s Forum theme, “Unleashing Educator Leadership,” sparked a networking opportunity unlike any other: The 2023 recipients met with veteran Milken Educators and education leaders from across the country to begin their lifetime membership to the national Milken Educator network. Recipients learned about powerful mentoring opportunities through the Milken Family Foundation to expand their leadership and impact and to strengthen the Milken Educator Network within their home states.

In 2023-24, 68 Milken Educators were surprised with their respective Awards at all-school assemblies as part of the Milken Family Foundation’s Journey to the 3,000^th Milken Educator. 2024 will reach $75 million in individual financial prizes spanning the length of the initiative and more than $144 million invested in the Milken Educator Award national network overall.

Rebello is serving in his fourth year as the Assistant Superintendent-Principal at Diman Regional Vocational Technical High School. Rebello’s journey in education includes leadership and administrator roles in Boston Public Schools and Fall River Public Schools.

During his tenure as Vice Principal at Durfee High School, Rebello demonstrated his ability to effect significant improvements. One of his most notable achievements was decreasing suspensions by 91%, a testament to his innovative approach to discipline and student support. Under his leadership, the Class of 2018 achieved the second-highest graduation rate in the school’s history.

As a central office administrator for Boston Public Schools, Rebello played a pivotal role in implementing Career and Technical Education programs district wide.

Under Rebello’s leadership, Diman Regional has witnessed growth and achievement. His initiatives to enhance teacher collaboration, student well-being, and academic achievement have significantly improved educational outcomes. Notably, he elevated the graduation rate to an impressive 98%, the highest in school history. Diman was rated as the highest-performing high school in the area and had the highest accountability rating. These accomplishments earned Rebello the National Milken Educator of the Year award from the Milken Foundation, which recognizes excellence in education.

Rebello’s leadership abilities have been widely recognized, leading to his appointment to the Economic Development Planning Council by Governor Maura Healey which develops strategies that promote economic growth through education. He has served on the DESE Focus Indicator Focus Group, the MSAA Educational Policy & Legislative Committee and is an active National Association of Secondary School Principals member. Rebello also serves as an MSAA Principal and Administrator Coach and is a member of the MSAA Board of Directors.

Rebello received a Bachelor of Arts in Psychology from Merrimack College in 2010, a Master of Education in 2012 from Frostburg State University, and a Certificate of Advanced Graduate Studies in Educational Administration from the University of Massachusetts Boston in 2016.