Drew Pratt '23

What stays with you when the final whistle blows and a new chapter begins? From Tower Hill wrestler to collegiate team captain, this month, we’re shining the spotlight on Drew Pratt ’23, a former Tower Hill wrestler who is now thriving as a student-athlete at Trinity College, where he studies Economics and serves as captain of the varsity wrestling team. His journey demonstrates the growth that comes from embracing challenges, building relationships and leaning into community. 

As we celebrate Drew, we invite you to join us for the Dwayne Hicks Spotlight Match taking place Saturday, Jan. 31, honoring the legacy of a Tower Hill wrestler whose impact still resonates today. 

Read on to hear Drew’s reflections on navigating academics, athletics and the experiences that shaped his path.

Editor’s Note: This Q&A has been edited for clarity and conciseness.

Tell us a little about where you are now. Describe your current role, field, or area of interest.

Hello! I graduated from Tower Hill in 2023, and I'm currently a junior at Trinity College in Hartford, Connecticut. Academically, I'm pursuing a Bachelor of Science in Economics with a minor in Formal Organizations with a concentration in entrepreneurship. I'm the captain of the varsity wrestling team at Trinity, competing with fellow Division 3 schools across the country. I am also serving as the president of my fraternity.

Thinking back to your time at Tower Hill, how did your experience here help prepare you for your journey?

As a student who entered Tower Hill in upper school from a public school setting, the biggest adjustment was definitely the coursework. Throughout 9th grade, it felt like I was drowning, and I was nervous that I wasn't prepared for the challenge. However, as I grew older and became more familiar with the school's culture and the resources around me, I continued to improve each year academically. The experience I gained by engaging with teachers and learning new study skills has prepared me well beyond what is required for a college-level workload.

As a former Tower Hill wrestler who now serves as a college team captain and campus leader, how did the leadership opportunities and close-knit community at Tower Hill help push you beyond your comfort zone and prepare you to lead, collaborate, and take initiative in college?

I believe that not only my captainship on the wrestling team at Tower Hill, but also the numerous leadership opportunities I had throughout high school, allowed me to excel in leadership positions in college. The opportunity to be in a small-school environment prepared me extremely well to make my voice heard, collaborate closely with peers, and take initiative in both academic and extracurricular settings. When I was forced out of my comfort zone, it made me develop new skills and form relationships that I would’ve never had.

What advice would you share with current Tower Hill students, recent graduates, or young alumni just starting out?

Tower Hill offers a unique opportunity to meet and connect with a wide range of people because of the school’s small size. Something I miss from Tower Hill is the little moments during the day and the ability to talk to everyone in the school, because everyone is so well-connected. My advice to current students would be to step out of your comfort zone socially. Introduce yourself to new people, have conversations youmight normally shy away from, and take advantage of the community's close-knit nature. Those relationships and everyday interactions end up being some of the most meaningful parts of the Tower Hill experience, and they’re what you’ll appreciate most once you leave.

We are so proud of Drew and his accomplishments! 

You can also connect with Drew and other fellow Tower Hill alumni by joining our newly created LinkedIn group! Serving as a private directory, you can network with those in your field, explore potential career paths and invite your Tower Hill alumni connections to this group. Help us grow and strengthen our alumni network!

Each month, we’ll feature alumni in this spotlight series shared in The Lookout newsletter and across our social media channels, highlighting the incredible work Tower Hill graduates are doing around the world. If you’d like to be included in an Alumni Spotlight, we invite you to submit this form.