By Robin Chandler '87

Dempsey Quinn is Hotchkiss's new director of athletics, effective July 1. He is also an instructor in mathematics, head coach of the varsity football team, and dorm head of Van Santvoord.

Quinn began his career as an independent school educator at the Berkshire School, where he taught math and coached football, basketball, and baseball. He left Berkshire to take up a football coaching position at Brown University, coaching running backs and tight ends. Quinn also recruited scores of student-athletes to Brown. He came to Hotchkiss in 2020.

Originally from Pittsfield, MA, Quinn is an accomplished athlete. He played three varsity sports at Avon Old Farms, and he was a three-year starter on the Cornell University football team. While at Cornell, Quinn earned a B.S. in industrial and labor relations. He subsequently earned an M.S. in coaching and athletic administration from Concordia University.

Quinn currently resides on campus with his wife Julia and their sons.

Learn more about Quinn in the Q&A below.

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Why did you want to become the next director of athletics at Hotchkiss? 

For me, being an AD has always been a career goal. Once I entered the boarding school world, it seemed like teaching and coaching was always the closest thing to playing. For a while it was an excuse for me to stay connected to the game, to the athletes, and athletics in general.  And as time went on, I wanted to get the most fulfillment each and every day. So this seemed like an obvious path, combining the best of both worlds—education and athletics. I go to work every day with faculty who want to be here to educate children, I still get to interact with the students each day, and I’m in the amazing boarding school environment. As AD, it will be different in that my focal point of every day will be athletics. That to me feels like the most fulfilling opportunity within the boarding school setting. I have enjoyed all my time in education and boarding schools, but I’ve always known that I would be most curious, excited, and interested in pursuing this particular path. 

What are your goals and the School's goals for Hotchkiss athletics, and how will you go about attaining them as you make the transition this summer?

The beauty of Hotchkiss is that we have the resources and the students who are motivated to do everything. Maybe going back to our roots a little and understanding what will be our pillar programs, core sports, or however we decide to define them—and to make sure those individuals and those teams are set up for success for the long term. That’s on the varsity side. I also want to take a long, hard look at what’s going on at the sub-varsity levels. We have a ton of programs. Evaluating if our students are actively participating, if they are getting outside and getting the exercise and support they need. We all know the physical, emotional, and mental health benefits of that, and we need to make sure that we are doing what we say we want to do within the co-curricular program. 

It’s very much about working together. It’s about failing and learning how to overcome failure, as well as learning how to communicate and understand how to take direction and be a positive member of a team. Because ultimately, that will be the long-term measure of success for those teams. Are our students growing through this process in positive ways? Are they finding joy in being a part of the co-curricular program?

How will you measure what success looks like? 

I think more of it will be a long-term process of listening to feedback as students leave Hotchkiss. Equally important is to have a formal process of real-time feedback. Looking at participation and attendance, are students offering positive anecdotes about their experience on a team? Are our coaches motivating, supportive, and invested in what they are doing? At the varsity level, I think we are a lot closer to that than we think; we are channeling, communicating, and putting structures in place that will help us continue to move forward. 

Fortunately, we don’t have problems with our athletes right now, culturally, and I think that speaks volumes to what we’re trying to do and how we are succeeding in that area. So now it's just making sure all teams are staffed appropriately and that the coaches are getting the support they need, and that we're continuing to push the envelope on the recruiting side with our admission process. 

The nucleus is there, which is a large reason why I was so excited about this opportunity. You’re not building something up from the ground; you're taking something that is already pretty darn successful and figuring out how to do it even better. 

What are your top five priorities for the coming year? 

1. Creating a little more clarity around what and who the athletic department is and the role that each person plays on a daily basis is really important, especially on the institutional side of things and for the faculty and students. 
2. I believe in creating clarity for our alumni base and our student body to understand that we can't do everything. Meaning, we don't want to do everything and be average; we want to excel because that's what we do here at Hotchkiss. We excel in the classroom, in music, in the arts, in our residential life program. And so that has to be consistent when you come across the street to athletics. So we need to properly identify and message this and what it's going to look like moving forward. 
3. I plan to look into carving out more time for professional development for our coaches and creating better support systems for them. Reviving the faculty athletic committee could be a useful tool. I also would like to focus more on the leadership training for our team captains—similar to what goes on in other areas of school so that we are delivering the same message across the board for all who live in the Hotchkiss community. 
4. Creating a more formalized feedback process for our coaches, one that levels up to what we do on the academic side. 
5. Continue to expand our social media presence and how we communicate what our athletes and teams are doing. That gets our kids excited, and it draws in kids who want to be involved with sports. Hopefully that will bring in another group of individuals who can be an integral part of helping us push the athletic program forward.

What are your thoughts on specialization?

I think we have a really good model in place and, objectively speaking, I think the girls sports have outperformed our boys sports as of late. It's no secret most of our girls—especially when you talk about stick sports—play three sports, or at the very least two sports. And so the depth that we have within those programs is unbelievable. 

I’ll use field hockey as an example. You might have a team with four or five college-level field hockey players, but add to that mix six or seven athletes who will go on to play a different sport in college, you’re going to have a very successful team. That is what we are looking to do, and finding a way to convey that model very clearly will be important. We also want to set some expectations that this is who we are and this is who we are going to be. It might be a little tricky in the first year or so, and we might miss out on some D1 college-level athletes, but hopefully we will get more of those college bound athletes who want to contribute in multiple ways. In the long run, this model will provide a foundation to sustain success. 

What are your thoughts on the role of our head varsity coaches in helping student athletes who aspire to play at the collegiate level? 

College recruitment is hugely important to many of our athletes. Obviously our coaches are going to do part-time admissions work because all the families that come through for visits and interviews are going to want to talk to them one-on-one in person. You have to invest a lot of time on the front end. Then on the back end you become a college counselor because no college coach is going to call the college office—even though our college office is phenomenal—they're going to want to talk to the high school coach and that person then becomes that key point person through the college recruitment process. So you’re really going to wear three different hats that are all very important to the larger process from when we get a student on campus to when we place them at the college level. 

I think there's a lot of opportunity to use the experience and knowledge that each one of our coaches has for their specific sport and kind of pool our resources to provide some internal professional development. There's a theme here—one of communication and clarity. The landscape has changed and we need to make sure we stay at least one step ahead. 

What do you see as the role of athletics in a school curriculum and how does it help with overall student development? 

Encouraging kids in an environment outside the classroom is very important as they are working with their peers and taking instruction from an adult. This is where failure is not only expected but encouraged; you learn to strain to overcome adversity in real time, you don’t have time to go back and study, in the flow of the game things are going to be happening that you have to deal with and respond to in the moment.  

As a player, you’re going to be working with kids who might not be your friends, they’re across grades, come from different backgrounds and perspectives, and you have to learn to come together as a team, communicate, and take feedback, criticism, work through adversity and learn how to rebound from failure. All these things are going to build these traits of resiliency that we know our youth needs. Not to mention, then you add on the mental health struggles we hear about every day. Let’s not argue with the proven facts about science—that the physical and mental benefit that you get from being outside and working in these team environments is critically important to our students. 

Looking back on your coaching career, what has been your greatest achievement to date, or what are you most proud of? 

I would have to say it was my first job as a head coach when I took over a fledgling football program that had a lot of struggles. I felt like in that season I grew up with my players. I am not saying that is the best way to do it, but now as I am able to look back on those moments as a 25-year head football coach, the students were as valuable to me as I hoped I was to them as far as my growth individually and then their growth as a team. Every day we were overcoming adversity together, learning on the fly. We hadn’t won a league game in three years and in year two, we went to the New England Championships. I think only two of those kids went on to play football in college, but that experience of really coming from the bottom and not knowing what it was like to find success on the field, and then getting to that moment where you truly were able to experience success at a high level, was incredibly impactful.  

Looking back, that has been one of my favorite seasons of coaching. It’s when things really started to click for me about how rewarding this job is, what’s important, and what isn’t important to be a leader and a coach. I will always put my finger on that year as my biggest year of growth, and it really set the stage for what it meant to be a professional and a role model; to know how to hold kids accountable, yet still be approachable while still trying to win football games, at the end of the day have everyone do their job well. 

In my professional life, I think it was when I was chasing that lifelong dream of coaching at the collegiate level. I loved what I was doing. I never felt like I was actually working a day in my life, but I was recently engaged and wasn't spending any time with my fiancée, and we knew this wasn't the life we were looking for. So fast forward a year: we're married and she's pregnant with our first child and it was at that moment I felt like somebody was shaking me saying, “this is what matters.” It's not all about the career, but it's about building your life as a whole. And I can stick that moment in time as a turning point for me when I realized I could chase this dream and sacrifice important things in my life, or I can embrace parts of my life that I love and find this other area from a career professional standpoint where everything blends together. And I can still be happy going to work everyday and still come home to my family at the end of the day. Basically I get the best of both worlds. 

Who are your role models and why? 

I'm a little old school when it comes to coaching, perhaps because I'm the son of a coach. My dad coached football and baseball for as long as I can remember, and my earliest memories are being on a sideline as the waterboy going to double sessions with him and his team. That's all I ever knew. When I was growing up I would come home from school and ask my mom to drop me off at practice. I took note of the  way my dad interacted with his players, which is funny because he was a warden, so he would  literally come from prison to the football field. Watching him turn off being a warden and then turn on his coaching personality was always a part of my upbringing. I've always looked up to my father, not only the father figure, but also as an incredible coach. He was my first favorite coach. 

When I went to boarding school at Avon Old Farms I had a football and basketball coach by the name of Tim Roller who scared the living daylights out of me; he was pretty intense, but he helped develop that thick skin you really need as an athlete. That’s something that would serve me well throughout my life. He could chew me out during practice, then an hour later I'd be eating dinner with him and his two young girls and we would talk about anything and everything. He taught me the value of how to accept this tough criticism, but then equally important, how to move on from it. He was the coach who would point out what went wrong, and then be the first person to pick them up and compliment them. That builds the trust and respect people have to have. He also ended up officiating our wedding, so it's that bond you have that goes way beyond the player/coach relationship, and that really struck a chord with me at an early age. 

What are the best attributes you’ve taken from coaches in your life that you think make for a quality coach?

Not to sound cliché, to be firm but fair. Set really really high expectations for your kids and hold them to it, but also understand some things aren't achievable in that moment. If you put forth a really good effort but come up short on the field, that's OK because you gave it your all. And there's still something to be proud of at that moment.

I think the other thing is that everything you do should have a purpose. We're not here to waste anyone's time. We're not here just to check the boxes to say we did it; that I had this drill or I had this conversation. Coaches should be really intentional in how they design their practice, how they talk to their players, and how they provide results-driven drills. Be very intentional and have a purpose with everything you do. Because if there's a purpose and an outcome that you're looking for, even in the short term you can get the most out of your players. 

What are you most looking forward to in your new role? 

For me it will still be about maintaining those relationships with the students and the faculty. But also just pushing everybody as an institution to raise the bar in athletics and to make sure we get there.

This place has been special to me for a while, so I feel very fortunate and excited for this opportunity. I don’t take the position lightly as I know there’s a lot of history there. I am just so thankful and ready to continue to move Hotchkiss athletics forward from here. 

What do you hope Hotchkiss athletics will look like five years from now? 

In five years I hope our athletic program is one that is full of energy and joy. Where the students and faculty, alike, are eager to get to practice and truly find comfort and excitement in the afternoons around campus. I want our teams to set the highest of standards when it comes to sportsmanship and make sure that all of our students play the game the right way. I hope there will be a uniform culture that demands our students give us the best versions of themselves and in return, we provide a journey that will leave them with lasting memories and lifelong friendships. I can't predict championships or banners, scholarships or awards, or wins and losses. However, I can guarantee that we will develop well-rounded student athletes and that they will be ready to become contributing members of society wherever their paths may take them.