Every teacher has a story beyond the classroom. Although Donald Kyle is well-known for teaching ninth grade English, being a top notch administrator, and for his famous email reminders, the Dean of Students’ story is much more complex. A rewind in time takes us back to Rye Country Day in the fall of 1968. He remembers it just like it was yesterday, “I was five coming to our school’s kindergarten the same year my mom started as a first grade assistant teacher.”

It is hard to imagine Rye Country Day four decades ago, much less attended by Kyle as a school kid through his teens. As many high schoolers do, Kyle said that free periods and hanging out with friends made school fun. In fact, he revealed “that I was not the school’s most accomplished student. But even in my youthful ignorance, I was aware that I had great teachers and was getting a great education… I always knew that the adults here were looking out for my best interest. Even when I was not being lovable, they were very loving.”

Athletics played a significant role for Kyle, a star varsity hockey goalie and football receiver. Kyle said one of his most successful football seasons can be attributed to his quarterback. “Basically, he would say ‘turn around at the thirty-yard line’ and the ball would be in my hands.” Kyle recalled how in a particular game against Brunswick, Rye recovered a fumble late in the game, and on the next first down: “the quarterback put the ball in my hands and I outran the Brunswick player and for a long time had the longest pass reception touchdown in RCDS. So I was a bit of a hero in the winter.”

In Kyle’s winter season that same year, he set another record he would prefer to forget. “In my not-so-good career as a hockey goalie, I set another record, which was more of an unofficial record, and it was a shot I let in. It was from the ultimate far end of the ice, a shot that should under no circumstances have gotten by me, as it wasn’t even a shot. It was an attempt by the opposing team to clear the puck. It was definitely, to use your generation’s language, a ‘hero to zero’ moment.” Well, he’s still the GOAT in the students’ books. 

Kyle quit hockey after junior year and said that he realized he wanted to focus much of his time and energy into practicing drums and performing with his band. This change prompted his real passion for playing in the ensemble and with his band that stuck together until college. He developed a love for playing music at a young age at RCDS. “I got a chance to perform a song with two of my classmates in sixth grade. We played Neil Young’s ‘Heart of Gold’ for our class. And when we were done, everybody freaked out like we were the best thing they’d ever heard, which we were not.” Who knows? Maybe the Upper School will get to hear an encore sometime.

What else has changed? He believes that students are facing a different scope of challenges far beyond the competitive nature of the college admissions process. Kyle noted that course selection alone was one of the biggest differences. A student taking a regular physics or calculus class had reached the upper levels of achievement, regardless of grades, while these courses are considered the baseline today. “The expectations of what an RCDS graduate of ‘22, ‘23, or 24, has to have accomplished is light years beyond what members of the Class of ‘81 needed to do.”

After college, Kyle says that he was more interested in becoming a rockstar than a teacher. However, in the summer of 1986 his fifth grade social studies teacher, also a former student, had left and the principal needed to fill the gap. The former head of school Dr. Pearson had always been a support figure, said Kyle. “I was living in Texas where I go to school and I was on the phone with my mom and complaining about difficulties finding a job and she said, ‘Why don’t you call Rye Country Day?’ I reminded her that I had not been Rye Country Day’s number one student, and she said I should call anyway. The school took a chance on me, and I will confess that I arrived here to do my first year thinking: I loved my time as a student here, but I have no idea if I can really do this job. And I completely fell in love with it. And that was thirty-seven years ago.” The rest, as they say, is history– even for an English teacher! 

Kyle emphasized that he will be forever grateful of his teachers caring for him and pushing him to his potential when he needed to be. In fact, he said this is one of the main reasons he continues to be a teacher today. “I have this hope that I can be some tiny, tiny portion of that for some other kid.”

As Kyle reflected on how his journey at RCDS has come full circle, he noted how reconnecting with his past was truly a gift. He now looks to the present and future: “I may be a teacher [or] administrator talking to a student now, but we have this other connection. Because technically, we’re both RCDS students in different generations. The multifaceted, three dimensional connection I have for this place will always mean a lot to me.” Kyle is intrinsically connected to Rye Country Day School, and his name will be remembered in its halls as a high school student and a teacher through multiple generations.