An English teacher who encourages students to turn argumentative essays into rap performances has received one of the most recognised honours in American education, along with an unrestricted cash prize of $25,000. His classroom approach combines creative expression with rigorous academic expectations, with 98% of his students achieving proficient or distinguished scores in on-demand writing assessments in 2025.Dr Tyler Saylor, who teaches English to students in Grades 11 and 12 at Harlan High School in Kentucky, became the first educator in Harlan Independent School District’s history to receive the Milken Educator Award. The surprise announcement was made during a school assembly on October 28, 2026, in the presence of students, teachers and education officials.The recognition places Saylor among a select group of educators honoured across the United States for their classroom achievements and potential to influence the teaching profession.
From essay-writing rap battles to stronger writing skills
Saylor’s classroom is designed to make students active participants in the writing process. According to his educator profile published by the Milken Family Foundation, he uses a writing-lab approach in which students develop arguments, strengthen their individual voices and learn to communicate their ideas effectively.One of his distinctive teaching methods involves essay-writing rap battles. Students write and perform rap songs as a way of presenting argumentative essays, combining creative expression with the skills required to construct and defend an argument.He also brings parents into the learning process by inviting them to attend student presentations, listen to podcasts produced by students and view their digital portfolios.The approach is accompanied by high academic expectations. In 2025, 98% of his students achieved proficient or distinguished scores in on-demand writing on the Kentucky Summative Assessment. The results reflect the performance of students in an area central to his teaching: developing clear arguments and effective writing skills.
First teacher from his district to receive the $25,000 award
The Milken Educator Award was established in 1987 by philanthropist and businessman Lowell Milken. Often described as the ‘Oscars of Teaching’, it recognises outstanding educators working across kindergarten to Grade 12 in the United States.Unlike awards that require candidates to submit applications or receive nominations, Milken recipients are identified through a confidential selection process. The educators are then surprised with the announcement, often in front of their students and colleagues.Saylor is Kentucky’s 65th recipient and one of up to 30 educators expected to receive the award nationwide during the 2026-27 academic year. The award includes an unrestricted $25,000 cash prize, which recipients can use as they choose. Saylor indicated that he intends to spend part of the money on classroom resources for his students.At the announcement, Kentucky Commissioner of Education Dr Robbie Fletcher and Milken Educator Awards Vice President Stephanie Bishop presented the honour.Reacting to the surprise, Saylor said his gratitude was directed towards his students, adding that seeing their reactions during the announcement was the greatest gift of the moment.
His work extends beyond the classroom
Saylor’s contribution to education also includes work at the state level. He has participated in the Kentucky Department of Education’s GoTeachKY Ambassador Programme and its Teachers Advisory Council, and is currently part of the Kentucky Innovative Teacher Cohort.He also developed a future-teacher scholarship to support a high school senior interested in pursuing a career in education. The initiative reflects his interest in encouraging more young people to enter the teaching profession.His academic qualifications include degrees in English education and education, a master’s degree in English, and a Doctor of Education specialising in educational leadership. He also works as an adjunct instructor and education studies adviser at a university.Beyond the cash prize, the award gives Saylor access to the national Milken Educator Network, which offers professional development, mentorship and leadership opportunities. He is also scheduled to attend an all-expenses-paid forum in Washington, D.C., bringing together award recipients and education leaders.For Saylor, the recognition was especially meaningful because it was shared with the students and colleagues who form part of his everyday teaching life. As he put it during the celebration, teaching is not merely his profession but an integral part of who he is.
