Editor’s Note: This article about long-time Upper School English teacher Dr. Roger “Doc” Hailes was originally published in 2014, when Doc was retiring from his decades of teaching at Collegiate. The Match is reposting it in honor of his passing on May 21, 2021. 

May 18, 2014

By Kyra Gregory

Hailes in his element.

After forty years of teaching at Collegiate, the legendary Doctor Roger Hailes is retiring. Doc began teaching in 1963 and came to Collegiate three years later in 1966. The school had just relocated to Mooreland Road and was still separated into the Boys’ and Girls’ Schools. When Doc first began teaching at Collegiate, the senior class held only forty-four boys, and Doc taught all of them. At the time, plays and other theater productions took place in Memorial Hall (now McFall Hall), and the only hang-out spot was the library. In 1976, Doc started teaching graduate school at VCU, and later taught at the University of South Carolina and the University of Richmond as well. After eight years, he returned to Collegiate to continue teaching Upper School English.

As a child, Doc attended an all-boys boarding school, and as he often tells his students, “Boys’ boarding school is the lowest form of life.” At boarding school, he felt like the teachers didn’t care about him or the other students. For this reason, Doc really appreciates the student-teacher relationships at Collegiate, where the students are cared for like children and create lasting relationships with the faculty. In high school, Doc played football and continued at Davis & Elkins College in West Virginia. As a college student, Doc remembers developing a close bond with his English professor in his second year, after the death of his parents. Doc’s mother was a teacher, and as he spent time with her in his childhood, he aspired to become a teacher himself. Hailes has three children: Brent, Roger Jr. (also called Baby Ra Ra), and Sarah. Roger is a stand-up comedian and writer (you can watch his videos on youtube) and Sarah runs a fashion company called Kirna Zabête (see her website HERE).

Hailes at the 2014 Upper School Closing Assembly upon his retirement.

Since he began teaching, both Collegiate students and faculty have greatly improved. Doc says that in the past few years, we have been “blessed with fabulous students” that, in his experience, are better than college students. Also, Doc enjoys the informality of interactions between students and teachers at Collegiate. When he was in school, students were very formal with their teachers, which did not allow for the close relationships that we create here at Collegiate. While he says he won’t miss the intensity of teaching in retirement, Doc will greatly miss the interaction with his students and teaching them challenging material, like Shakespeare, which “really gets their eyes big.”

After forty years of teaching, Doc Hailes has made quite an impact on Collegiate School. He has introduced countless students to Hamlet, been featured in a plethora of foreign film projects, graded an infinite amount of essays, and given almost every student in the school a nickname. He’s also taught many children of former students. After being in his class this year, I can see how much he cares for his students and wants them to succeed. Doc understands the importance of true education and wants his students to get the most out of school and appreciate their education. He is a teacher who loves teaching, loves the material, and loves his students. From the whole Upper School, I can say that next year Doc Hailes will be greatly missed, and his legend will live on for years to come.