Athlete of the Issue: Dillon Cleary ’20

Dillon Cleary ’20 is a four-year member of the Varsity Baseball Team.

Dillon Cleary ’20 is a four-year senior and four-year member of the Boy’s Varsity Baseball team. Cleary is also on the JV Cross Country team in the fall. Teammate Carlos Martinez ’22 said, “[Dillon is] one of the hardest workers on the team. He puts in a lot of work and pushes us all until we have nothing left.  He’s also super passionate and it shows in games when he speaks and plays. He’s also good company, we all love to be around Dillon. He’s a funny guy who’s kind and relatable.”


What do you love most about baseball and the team?

The best part of playing baseball at Hotchkiss is definitely the guys. Out of all the teams I’ve been a part of at Hotchkiss, the baseball team will always be the closest-knit team. Ever since my [Prep] year, the upperclassmen have looked out for the underclassmen [to] make them feel welcome and [to] support them. [The upperclassmen] know that [the underclassmen] are going to be the future of the team in a couple of years. This was my Senior year, and we [wanted to] look out for the underclassmen because we were once looked out for by our Seniors. 


What were you looking forward to most about this season?

Honestly, this was the best Hotchkiss baseball team I’ve ever been a part of talent-wise. In my freshman year, we only won four games, but every year there’s been constant improvement. We won seven games the next year. This year was going to be our year; we really had a shot of being one of the best teams in the league, and [to] compete with teams such as Avon and Taft that have always beat us in past years. We were fortunate enough to be able to go on our spring trip in the first week of spring break. We went down to Florida for a week, played four games, and won every game. We really got to bond, and at that point we didn’t know our season was going to get canceled. We really clicked with each other right away, and you could tell that there was chemistry. 


What has been your favorite memory or highlight from a previous season?

In my [Lowermid] year, we had a game at Dunkin’ Donuts Park in Hartford, which is where the Double-A Hartford Yard Goats, affiliated with the Colorado Rockies, play. It was the most insane stadium I’ve ever played in. Our game was against Choate. We [hadn’t] beaten Choate since my [Prep] year, and we play them twice every season, because they’re a Founder’s League team. It was a night game and there were a bunch of people in the massive stadium, and I was pretty nervous, because I got to start in the outfield. It was a close game and went back-to-back every inning. They would score a couple of runs, and we would score a couple of runs. Then I actually got called in to pitch towards the later end in the game. Assistant Coach William Boscow looked me in the eye and said, “Act like you’ve been here before,” and I took that mindset to heart. We were down by one run, and it was the last inning with two outs. I remember Josh McCarthy [’18] was down to his last strike and the fans thought the game was over, but the team knew that the game wasn’t [over] even though we had nobody on [base] and no real momentum. McCarthy swung at strike three, but there’s this rule in baseball [that] if the catcher drops the ball at strike three, the batter can run to first base before the catcher throws him out. The catcher missed the ball and Josh advanced to first, so we had a runner on base. We had the momentum, one thing led to another, and before you know it, it was second and third with two outs and it was the bottom of the last inning. Max Quinn [’19] stepped up to the plate and hit a double down the line and walked it off against Choate. 

After Max ripped that double down the line, everyone  stormed out of the dugout and started mobbing him. For the rest of the year we had steam and went on to beat some teams that we never thought we could. It also meant a lot to Coach Wosleger because his  dad is the Head Coach of the Choate team; it was the first time he was ever able to beat his dad. 


What advice would you give to a current or future athlete at Hotchkiss?

Listen to the advice that your elder teammates have to give, especially [students] who have been in the program for a while. They know what it’s like to be a student-athlete at Hotchkiss, and it’s not easy. Also, listen to your coaches. They always have something important to say. It’s easy to brush off something the coach says because you don’t agree with it, but we have great coaches at Hotchkiss. They always want the best for you and they’ll always give you advice that’ll help you become a better person and a better player. Just listen to your coaches and listen to your other teammates, because they always know what’s best for you even if you may not think it at the time. 


Who has inspired you the most and what have they done to impact you?

Bobby Doar ’18 taught me a lot. He was an Upper Mid my Prep year. I always looked up to Bobby because he was a center fielder and a pitcher, [which] are my positions, and he always plays the game right. Bobby isn’t cocky; he doesn’t have an ego. He hustled every ball out, ran after every ball in the outfield, and never talked back to an umpire. He’s just a stand-up guy on and off the field. He was also a great example of a student-athlete. He took me under his wing, and I’m so grateful for that. I’ve looked up to him ever since [then]. I try to play the game like Bobby would play it. I [looked] up to Bobby, and now I’m in his shoes. I hope I can be an example like Bobby to younger players on the team.