A gifted administrator, business owner, and coach, Mr. Kelly serves as Deerfield Academy’s Student Life Office Senior Associate, bringing a wealth of knowledge and experience to the dean team. He is the Girls Junior Varsity Head Basketball Coach and Boys Varsity Assistant Baseball Coach. From 1998 to 2012, Mr. Kelly held a variety of leadership positions at Deerfield Elementary School, including Assistant Principal, Principal, and Special Education Teacher. During his tenure at Deerfield Elementary, Mr. Kelly was responsible for school-wide discipline and safety, professional development, and staff evaluation.
For many Deerfield students, Mr. Kelly embodies the school’s essential spirit and its core values of integrity, compassion, and grit. In the words of Captain Deerfield Caleb Kirkpatrick ’24: “Mr. Kelly is like a beacon, a source of what Deerfield is for me. He consistently radiates kindness, and leads our community with a level head and a love for this place that I try to emulate.”
The first thing a visitor notices when entering Mr. Kelly’s office is a large paperweight on his desk etched with the words, “Listen here, Cupcake.” The token, a gift from the Class of 2019, is a reference to Mr. Kelly’s colorful storytelling and straight-talking style. Entering his twelfth year at Deerfield Academy this month, Mr. Kelly took a moment to speak with the Scroll.
LW: What originally brought you to Deerfield?
KK: My wife [Deerfield Academy Language Teacher Xiao Feng Kelly] was hired at Northfield Mount Hermon School, and we were there for four years, as I was at Deerfield Elementary. My boss came over to the house one night and shared that Deerfield Academy was looking for a Chinese teacher. At that time, we had no particular desire to leave Northfield Mount Hermon, but my boss told my wife that she owed it to herself to go down there and listen to Eric Widmer, who was the headmaster at the time. So that’s how it all began. My wife built a tremendous relationship with Mr. Widmer, who wanted her to expand the Chinese Language program, and twenty-four years later, here we are!
LW: For many students, you embody a lot of essential DA values. What does Deerfield mean to you?
KK: Well, on one level, it means home to me. Both my daughters were raised here and both attended Deerfield, as well. I love the Academy and I love what it stands for. We focus on a group of students who are away from their families, many for the first time, and we help to shape and develop these outstanding young people during their most formative years. The young adolescent who enters Deerfield as a ninth grader is not the same young adult who leaves us four years later. I feel this obligation and commitment to our students is what makes Deerfield so special.
LW: What is your happy place?
KK: Caratunk, Maine. We have a log cabin on the beautiful lake.
LW: Favorite food?
KK: My wife’s cooking. Specifically, her dumplings.
LW: Favorite music?
KK: I guess I’m an oldies guy. I like music from the 60s and 70s. In high school, the Allman Brothers and Earth, Wind, and Fire were two of my favorites!
LW: Favorite movie?
KK: Rudy [1993 biographical film about Daniel “Rudy” Ruettiger, who overcame obstacles to pursue his dream of playing football for Notre Dame]
LW: Which living person do you most admire?
KK: I have a tremendous amount of respect for Ms. Creagh [Deerfield’s Associate Head of School for Student Life]. Her commitment to this school and every student who attends Deerfield is unmatched; she’s special. Also, I admire my previous boss at Deerfield Elementary, who was one of the very best, from the complete perspective of what it means to be an administrator.
LW: What is the quality you most strive for in yourself?
KK: You want to practice what you preach. I live by a motto given to me by my mentor: “When working with a student, ask yourself, if this was my son, if this was my daughter, how would I like them to be treated?” I strive to hold myself to that standard.
LW: Which words or phrases do you most overuse?
KK: My wife would say, “Don’t worry about it.” When I say that to my wife, it drives her crazy.
LW: Which talent would you most like to have?
KK: I wish I were a better writer. Also, my daughter and I play the drums, so I wish I could improve my drumming skills.
LW: What do you consider your greatest achievement?
KK: My children, my family! Also, publishing Both Sides Of The Line [Mr. Kelly’s account of his mentor Jack Clyde Dempsey’s life.]
LW: What is your favorite hobby?
KK: I love to shoot pool, play chess, and read.
LW: Who is your favorite hero of fiction or film?
KK: I would say some of Clint Eastwood’s characters. His characters prioritize good over evil, and they’re unapologetic about it.
LW: Which historical figure do you most admire?
KK: One of them would be George Washington. He had the fortitude to stick with his vision. He didn’t believe he was going to win, but he was a purist and he believed in the cause. Two others I admire are the Wright Brothers. Knowing full well that they had no engineering background, the years of trial and error, the commitment they put in for something they believed in—to me, that’s miraculous. I also think of one of my football coaches. He lived two different lives; he had been a criminal, but at the same time he was one of the greatest coaches I ever had. The positive attributes that he projected onto us I carried forward in my own coaching.
LW: What is your motto?
KK: Maximize your journey.
LW: A final question: what advice would you give to your 18-year-old self?
KK: Don’t be afraid to follow your dreams. I think when people reach my age, the biggest source of regret is that they didn’t follow their dreams. It doesn’t matter if you succeed or fail. It’s about having the guts to go out and try and give it a shot. And I think if you look back at your life and you’ve done that, you’ve lived a good life.