Dr Tyler Saylor, an English teacher at Harlan High School in Kentucky, has received the Milken Educator Award and an unrestricted cash prize of $25,000 for his approach to teaching writing, which includes turning argumentative essays into rap performances.
The award was announced during a school assembly on October 28, 2026, making Saylor the first recipient from Harlan Independent School District. He teaches English to students in Grades 11 and 12.
According to the Milken Family Foundation, 98% of Saylor’s students achieved proficient or distinguished scores in on-demand writing assessments in 2025. His classroom approach focuses on helping students develop arguments, communicate ideas clearly and strengthen their individual writing styles.
Turning essays into performances
Saylor’s writing exercises ask students to write and perform rap songs as a way of presenting argumentative essays. The activity requires them to develop a position, organise their reasoning and communicate their arguments to an audience.
He also invites parents to engage with students’ work by attending presentations, listening to student-produced podcasts and viewing digital portfolios. The approach combines classroom instruction with opportunities for students to present their work beyond written assignments.
Saylor’s work extends beyond his English classes. He has participated in the Kentucky Department of Education’s GoTeachKY Ambassador Programme and its Teachers Advisory Council. He is also part of the Kentucky Innovative Teacher Cohort and developed a scholarship to encourage high school students to pursue careers in teaching.
How the award works
The Milken Educator Award was established in 1987 by philanthropist Lowell Milken. It recognises educators across the United States for their achievements and potential to contribute to the teaching profession.
Unlike awards that require applicants to submit nominations, Milken recipients are identified through a confidential selection process. The foundation says it looks for educators whose work has already made an impact and who show potential for further contributions to education. Each recipient receives an unrestricted $25,000 prize.
Saylor is Kentucky’s 65th recipient since the state joined the programme in 1993. Awardees also join a national network that provides professional development, mentorship and opportunities to take on wider leadership roles in education.
What the writing scores measure
The results cited by the foundation come from Kentucky’s Summative Assessment, the state’s annual assessment programme for public school students. The assessment measures progress against state academic standards and includes writing tasks that require students to demonstrate their skills through extended responses.
Kentucky classifies student performance as Novice, Apprentice, Proficient or Distinguished. The state education department cautions that assessment scores are one measure of student learning and should be considered alongside classroom work, grades and other assessments.
The 98% figure refers specifically to Saylor’s students’ on-demand writing results in 2025. It does not represent the overall performance of Harlan High School or the state’s students.
Saylor has said he intends to use part of the award money to purchase classroom resources. He is also due to attend a Milken Educator Awards forum in Washington, DC, in June 2027, where award recipients and education leaders will meet to discuss their work.