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Harlan High’s Hardworking English Teacher Surprised with 2026 Kentucky Milken Educator Award and $25,000

Dr. Tyler Saylor’s continuous encouragement and structured support for students recognized on a national level

October 28, 2026

SANTA MONICA, Calif. — It’s Halloween season in Harlan County, and leaders from the Milken Family Foundation and Kentucky Department of Education have a few treats up their sleeves for one unsuspecting teacher! At a school celebration this morning at Harlan High, Kentucky Commissioner of Education Dr. Robbie Fletcher commended the accomplishments of staff and students, then announced that a special guest had additional news to share with the students, colleagues, dignitaries and media assembled. As the gymnasium buzzed with anticipation, Milken Educator Awards Vice President Stephanie Bishop stepped up to the mic to unveil a surprise Harlan High will never forget: Dr. Tyler Saylor, 11th and 12th grade English teacher, is the 2026 Kentucky recipient of the Milken Educator Award and an unrestricted cash prize of $25,000! 

Along with the financial award, Dr. Saylor will join the prestigious ranks of Milken Educators coast-to-coast. The Milken Educator Awards, celebrating 40 Years of Elevating Educators, have no formal applications or nominations. Outstanding K-12 educators 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. 

“The intentionality and care infused into Dr. Tyler Saylor’s instruction are palpable,” said Bishop, who is also a 2001 Virginia Milken Educator. “He is exactly the kind of teacher, motivator, and mentor every student should have throughout life’s exciting journey of learning, wonder and self-discovery. Welcome to the Milken Educator family, Tyler. Congratulations!” 

Dr. Saylor is Kentucky’s 65th recipient since The Bluegrass State joined the Milken Educator Awards program in 1993. He is the first-ever recipient in Harlan Independent Schools. 

“I am proud to be here to honor Tyler Saylor, an educator who has devoted his entire career to making sure the students in Harlan receive as solid and engaging an education as any student in the Commonwealth,” said Dr. Fletcher. “He encourages his students to aim high and chase after their dreams. It is educators like Dr. Saylor that gave me the skills and confidence to pursue my dreams, which has led me to where I am today.” 

The Milken Educator Awards 40th Anniversary Tour will honor up to 30 educators this school year—adding to the Milken Educator Network of more than 3,000 professionals nationwide. Since the Awards’ first presentation in 1987, more than $76 million in individual cash prizes and over $147 million has been invested in the Milken Educator Award national network overall, empowering recipients to broaden their impact and encouraging young, capable people to consider a career in education. 

More About Dr. Tyler Saylor 

An Encouraging Presence: Dr. Tyler Saylor inspires his students to think like scholars in his 11th and 12th grade English classes at Harlan High School. He transforms his classroom into a writing lab where students fully immerse themselves in the process, learning how to craft compelling arguments, strengthen their voice and take readers on a journey through their words. Saylor pairs this approach with rigorous instruction and high expectations, challenging students to push beyond their comfort level. Students recognize the value of Saylor’s challenging methods, oftentimes returning to Harlan to share success stories and crediting his teaching with helping them build confidence and critical-thinking skills in their writing abilities. This type of vibrant learning creates a bridge between high school, higher education and life beyond the classroom with clear results. Saylor’s students consistently rank among the top performers on the state summative assessment, with 98% achieving proficient or distinguished scores in on-demand writing in 2025. 

Making Learning Fun: Saylor regularly integrates innovative instructional practices in his classroom and builds relationships with his students and their families. He created essay-writing rap battles where students wrote and performed rap songs as a form of argumentative essay writing. Parents are invited to participate in their child’s education by visiting and observing presentations and projects, listening to student-produced podcasts and viewing digital portfolios. 

Broadly Impactful Work: Saylor’s leadership and influence extend beyond Harlan to the statewide level. He served in the Kentucky Department of Education’s GoTeachKY Ambassador Program and on the Teachers Advisory Council, where his classroom experience and perspective were vital to the group’s missions of attracting, supporting and retaining effective educators across the Commonwealth. A byproduct of this work was his development of the GoTeach future teacher scholarship to inspire and support high school seniors interested in pursuing education as a career. 

Education: Saylor earned his Bachelor of Arts in English education with secondary certification in 2019 and his Master of Arts in education in 2022 from Union Commonwealth University, where he now serves as an adjunct instructor and education studies advisor. He went on to receive a Master of Arts in English from Arizona State University in 2022 and a Doctor of Education with a specialization in education leadership from Liberty University in 2024. 

The Milken Educator Award Reaps Lifelong Benefits

• The $25,000 cash Award is unrestricted. Recipients have used the money in diverse ways. Some recipients have spent the funds on their children’s or their own continuing education, financing dream field trips, establishing scholarships, and even adopting children.
• Honorees receive powerful mentorship opportunities for expanded leadership roles that strengthen education practice and policy. Milken Friends Forever (MFF) pairs a new recipient with a veteran Milken Educator mentor; the Expanding MFF Resource and Explorer Program fosters individual veteran Milken Educator partnerships around specific topic areas; Activating Milken Educators (AME) promotes group collaboration in and across states to bring solutions to pressing educational needs; and the Milken Educator Collective connects recipients with shared content areas, grade levels, or professional roles. Milken MeetUps abound across the nation to deepen learning and connection and expand innovation in education.
• The honorees will attend an all-expenses-paid Milken Educator Awards Forum from June 4-6, 2027, in Washington, D.C., where they will network with their new colleagues, as well as veteran Milken Educators and other leaders, about how to amplify their voices as beacons of excellence in the profession.
• Veteran Milken Educators demonstrate a wide range of leadership roles at state, national and international levels. 

The Milken Educator Award might come to a community near you! Who will be next? Join us as we surprise these remarkable individuals and celebrate their dedication to excellence in education! Follow the tour and use the #MEA40 and #MilkenAward hashtags on: YouTube (MilkenAward) | Facebook (MilkenEducatorAwards) | Instagram (MilkenFamilyFdn) | TikTok (MilkenAward) | X (Milken) | LinkedIn (MilkenFamilyFdn). 

Visit MilkenEducatorAwards.org or call the Milken Family Foundation at (310) 570-4772 for more information.

About the Milken Educator Awards: “The Future Belongs to the Educated”
The first Milken Educator Awards were presented by the Milken Family Foundation in 1987. Created by philanthropist and education visionary Lowell Milken, the Awards provide public recognition and individual financial rewards of $25,000 to K-12 teachers, principals, and specialists from around the country who are furthering excellence in education. Recipients are heralded in early-to-mid-career for what they have achieved and for the promise of what they will accomplish. The Milken Family Foundation celebrates over four decades of elevating education in America and around the world. Learn more at MFF.org.

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