Tyler Saylor hugs a teacher while other teachers smile and clap.

Tyler Saylor, an English language arts teacher at Harlan High School (Harlan Independent), hugs a colleague after finding out he was the latest recipient of the Milken Educator Award. Photo by Joe Ragusa, Kentucky Department of Education, Oct. 28, 2026

(HARLAN, KY) – Tyler Saylor, an English teacher at Harlan High School (Harlan Independent), was honored with the Milken Family Foundation National Educator Award during a surprise ceremony at the school on Oct. 28.

“I feel so, so blessed to be amongst the greatest faculty and staff in the state. I honestly feel like I should share this award with all of them, too, because they are just as worthy of this award as well,” Saylor said. “And so, I just feel incredibly honored to receive this today. And when I heard my name, I just became so overjoyed with emotion. … I don’t know how I kept it together without crying, but I somehow kept it together.”

The prestigious honor, hailed by media as the “Oscars of Teaching,” has recognized outstanding teachers for 40 years.

Commissioner of Education Robbie Fletcher joined Milken Educator Awards Vice President Stephanie Bishop to present Saylor with the award, which includes a $25,000 unrestricted cash prize, during an assembly with students, faculty, district leaders, state government leaders and community members.

“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,” Fletcher said. “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.”

Colleagues praised Saylor for transforming his classroom into a writing lab where students fully immerse themselves in the writing process, learning how to craft compelling arguments, strengthen their voice and take readers on a journey through their words. They also said Saylor pairs this approach with rigorous instruction and high expectations, challenging students to push beyond their comfort level.

Harlan Independent Superintendent Jennifer Parsons said Saylor goes beyond expectations to assist students in becoming the best version of themselves.

“Dr. Saylor combines high expectations with meaningful rigor, while meeting the needs of every student,” Parsons said. “He challenges each learner to reach beyond what they thought possible, providing them the support needed to succeed, and creates an environment where every student feels valued, capable and inspired to become the very best version of themselves.”

A group of people stand smiling in a gym, holding a large check made out for $25,000.

Tyler Saylor poses with a ceremonial check representing the $25,000 prize that comes with the Milken Educator Award. Pictured, from left: Commissioner of Education Robbie Fletcher, Milken Educator Awards Vice President Stephanie Bishop, 2021 Kentucky Milken Recipient Kevin Dailey, Saylor, 2025 Milken Recipient Sydney Newton, Kentucky Department of Education Program Consultant Allie Green, Harlan High School Principal Mike Bolton, and Harlan Independent Superintendent Jennifer Parsons. Photo by Joe Ragusa, Kentucky Department of Education, Oct. 28, 2026

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.

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 Scholarship, designed to inspire future teacher scholarship and support high school seniors interested in pursuing education as a career.

“One of the most meaningful parts of the GoTeachKY Ambassador experience was being challenged to think about how we can actively support and elevate the teaching profession,” Saylor said. “This scholarship became a way to invest directly in a future educator.”

Saylor earned his bachelor’s degree in English education with secondary certification in 2019 and his master’s degree 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’s in English from Arizona State University in 2022 and a doctorate with a specialization in education leadership from Liberty University in 2024.

The Milken Educator Awards 40th Anniversary Tour will honor up to 30 educators coast to coast, adding to the Milken Educator Network of more than 3,000 professionals nationwide. Created by philanthropist and education visionary Lowell Milken in 1987, the Milken Educator Awards represent America’s pre-eminent educator recognition initiative, inspiring educators, students and communities to “Celebrate, Elevate and Activate” the K-12 teaching profession.

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.

The Milken Educator Award is not a lifetime achievement honor. 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. 

All of the Milken 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.

In addition, they enter the Milken Friends Forever mentoring program, where freshman Milken Educators receive personalized coaching and support from a Milken Educator veteran on ways to elevate their instructional practice and take an active role in educational leadership, policy and practice.

For more information about Newton and links to photos and a video from the ceremony, visit the Milken Family Foundation National Educator Award website.

Read more about recent Kentucky Milken winners: