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My Experience as the First Female Captain Deerfield
Bailey Cheetam '19 Contributing Writer
January 30, 2019
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When I first found out I was in contention for the position of Captain Deerfield, I didn’t know what to think. I felt incredibly intimidated at the thought of being the first girl in this position. While I knew there would be a day when a female student took on the role, I never thought that student would be me.

Finally, the day came when Mikey Holland and I stepped to the front of the stage to take on our roles as Co-Captains Deerfield. As confusion and excitement spread throughout the crowd, the position that I had always respected and revered was offered to both of us.

Credit: Deerfield Academy Flickr
Co-Captain Deerfield Bailey Cheetham ’19 leads cheers at the girls varsity volleyball game on Choate Day.

I have always felt incredible pressure to live up to the expectations of past Captains Deerfield and to prove that I am deserving of the role. Traditionally, Captain Deerfield has towered above students, yelling at crowds with a deep voice. However, I am a 5’ 4” girl with a high-pitched voice and uncontrollable energy, and my presence marks a departure from the traditional Captains Deerfield before me. That being said, I have learned from my experience that it is possible for someone like me to receive the same attention and respect that has traditionally been awarded to the previous Captains.

Captain Deerfield is and has always been responsible for pushing boundaries  and fueling the energy that feeds our athletes and artists. This is what makes Deerfield special. With my role as the first female Captain Deerfield, I knew I was stepping into a whole new realm of pushing boundaries.

A week before Choate Day, shortly after a massive downpour, the boys varsity football team beat Cheshire Academy 34-14 in a huge upset. Post-game, the football players went racing into practice fields that had flooded with four feet of water. From the hilltop, I watched the boys celebrate their victory as they dunked themselves in mucky water.

One of my friends challenged me, “What are the odds you would jump in with them?”

I responded with, “Heck, let’s do it.”

I hit it down the hill and jumped head first into the brown water. The Captain Deerfield costume was drenched, with the white now a light shade of brown and the green several shades darker, but it was 100% worth it. Captain Deerfield isn’t just about watching our teams compete; it is about being a part of celebrating our teams’ victories.

At our Pep Rally the night before Choate Day, I was in charge of leading our “Hail Deerfield” chant. The crowd’s response was more than what I could have asked for. After hearing “Hell No” to hailing Choate, I finally felt like I was a part of something bigger than my role as Co-Captain Deerfield. I felt a new sense of family. I was humbled by the outpouring of support and respect that this small but pivotal moment offered. Captain Deerfield is a position that can’t be successful alone; it is a position that needs the heart of the whole Deerfield student body.

The morning of Choate Day, I woke up to a rush of encouragement. The support from alumni and students empowered me to believe that I was capable of being Captain Deerfield. I vividly remember the girls varsity volleyball game. Energy was high, kids were engaged, and the Choate cheers were ready to roll. Although the girls didn’t get the win, it was a hard-fought game, and it was a time that I won’t forget as the peak of my Choate Day experience. Captain Deerfield should always go in seeking victories, but accepting the losses with dignity.  Our traditional post-game Fight Song is the epitome of this mentality. That is something special.

No experience in life will be perfect. Holding the position as a female Captain Deerfield has not been easy—I won’t sugarcoat it. At times I’ve doubted myself, been intimidated by my classmates, and felt hesitant about whether or not I could live up to the standard to which I believe Captain Deerfield should be held.

But more importantly, I have experienced so much encouragement, love and support. Thus far, this year as Co-Captain Deerfield has been incredibly enriching. I recognize that I have improvements to make, and I won’t be perfect. I want to thank Mikey for navigating this journey with me and supporting me when I needed it the most.

For the younger and future students of Deerfield, Captain Deerfield should be a role that embodies the true spirit of Deerfield. Regardless of your height, the pitch of your voice, or any other aspect that characterizes you, what really matters is your love for this place and the overwhelming joy you get from supporting Deerfield talent.