Caleb Ockman 鈥�21 arrived at 淫人色欲社 as a 14-year-old freshman with a clear goal: to pursue high-level soccer in the United States while earning a strong academic foundation. Four years later, he graduated as a scholar, a linguist, a leader鈥攁nd now, just a few years beyond the Hillside, a Fulbright finalist bound for Turkey.

鈥淚t started with soccer,鈥� Caleb recalls. 鈥淚 came to South Kent thanks to Owen Finberg, who helped me understand that this was the place where I could do both鈥攄evelop as a player and as a student. That was the original goal: play for a top prep team and eventually play in college.鈥�

Caleb committed to Williams College in the summer before his senior year, during the height of the COVID-19 pandemic. He entered Williams as a recruit for the varsity soccer team, intending to double major in French and political science. But like so many transformative stories, his path quickly evolved.

鈥淭he coach who recruited me left before I arrived,鈥� Caleb says. 鈥淭he new coach had a different style, and it just didn鈥檛 click. D3 athletics are intense, but they鈥檙e not supposed to be your whole life. I made a tough decision to step away from the team.鈥�

What followed was a flourishing of intellectual curiosity. 鈥淥nce I left the team, I had time and space to explore,鈥� he says. 鈥淚 joined the student newspaper and a foreign affairs journal. I started sailing鈥攕omething I鈥檇 never done before鈥攁nd became a tutor in Russian. I started taking courses that challenged me in entirely new ways.鈥�

Caleb鈥檚 interest in Russian wasn鈥檛 entirely new. As a child traveling with his parents, Caleb lived in Bulgaria, Ukraine, Serbia, and Kenya where he had early exposure to Slavic languages and Eastern European culture. That

background shaped his decision to double major in history and Russian while still completing coursework in French and political science.

South Kent played a crucial role in helping Caleb hone his academic focus. He credits Father Steve Klots with pushing him to think more deeply and engage more fully with his studies. 鈥淗e was instrumental in helping me find purpose in the classroom,鈥� he says. 鈥淎t South Kent, you鈥檙e never just a number. People see something in you and help bring it out.鈥�

That ethos鈥攐f seeing potential and investing in it鈥攃arried Caleb through his time at Williams and into the wider world. In the spring of his junior year, he studied abroad in Kazakhstan through Middlebury鈥檚 rigorous Russian immersion program, taking university courses entirely in Russian and pledging not to speak any other language during his stay.

One of those courses鈥攁 class on the international relations of Central Asia鈥攚ould profoundly shape Caleb鈥檚 academic and professional direction.

鈥淲e studied the region鈥檚 geopolitics, from the fall of the Soviet Union to the present, and the role of players like Turkey,

China, and Russia,鈥� he says. 鈥淭hat course made me realize I wanted to pursue a career in foreign policy鈥攁nd that to understand Eurasia, you can鈥檛 just know Russian. You need to understand Turkey.鈥�

That realization sparked his Fulbright application: a proposal to study in Turkey, deepen his understanding of Turkish language and culture, and explore Turkey鈥檚 unique geopolitical position as a bridge between East and West.

The application process was long and uncertain. Caleb applied in the fall of his senior year and waited months for a decision鈥攆irst as a semifinalist, then as an alternate, and finally, in late May, as a confirmed Fulbright finalist.

Now preparing for his year in Turkey, Caleb is weighing placement offers from two universities in Istanbul. 鈥淚t鈥檚 a good problem to have,鈥� he laughs. 鈥淏oth programs are excellent. I鈥檓 choosing between different course offerings, housing options, and how far I鈥檒l be from the city center. But either way, I鈥檒l be immersed in a region I care deeply about.鈥�

Though his path began with soccer, it has expanded into a world of diplomacy, cultural fluency, and global citizenship. Caleb

co-founded Williams鈥� first campus foreign policy group鈥攁 student-run think tank of sorts that hosts weekly discussion sessions, produces research, and mentors undergraduates interested in policy careers. The group grew from a handful of students to over 45 by his graduation.

Looking ahead, Caleb is exploring opportunities with think tanks and government agencies in Washington, D.C., including roles in foreign policy analysis. He鈥檚 also considering graduate study in law or international relations, though he鈥檚 quick to point out that practical experience will come first.

鈥淚 want to work. I want to be in the field鈥攚hether it鈥檚 through the State Department, a federal agency, or a policy institute,鈥� he says. 鈥淚 care deeply about this region because I grew up there. I鈥檝e seen the challenges people face, especially in Ukraine, where I lived for part of my childhood. If I can contribute to a better future for that part of the world, that鈥檚 what I want to do.鈥�

From the quiet calm of the Hillside to the complexity of Central Asia, Caleb Ockman鈥檚 journey is a testament to what South Kent strives to instill in every boy: resilience, curiosity, and a sense of purpose. As he steps into his Fulbright year, he carries with him the values that shaped him鈥攁nd a clear vision for the difference he hopes to make.

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鈥淎lumni Weekend on the Hillside is always a special occasion. It’s an opportunity to renew old friendships, and to reminisce about experiences in the classrooms and on the playing fields. They say you can’t go home again, but Alumni Weekend is as close as it gets,鈥� Peter Thompson 鈥�67.

Thursday, June 5: Tee Off the Weekend
The festivities begin off campus with a friendly Golf Outing and Dinner at River Oaks Golf Club. It鈥檚 the perfect way to ease into the weekend鈥攃atching up with old friends, enjoying the scenic views, and celebrating the start of Alumni Weekend together.

Friday, June 6: Adventure, Stories, and Celebration on the Hillside
Friday kicks off with a tradition of camaraderie and adventure, as the leads a Hike to Bull Mountain, inviting all alumni to stretch their legs and take in the natural beauty that makes South Kent so special.

In the afternoon, head to Bringhurst Auditorium for Post Pigtail Perspectives to hear brief presentations on impactful experiences and insights.
Then, it’s game time! Grab a glove or cheer from the sidelines during a fun Alumni Softball Game.
As the sun sets, we鈥檒l gather for Cocktails in the Courtyard and then it鈥檚 time to head off to your class dinner at your favorite restaurant in town.

Saturday, June 7: A Day to Remember
Start your Saturday with a warm Welcome from the Head of School and hear inspiring updates from current South Kent faculty about the exciting work happening on campus today.

Next up is a fan favorite: the Annual “In My Day” Memories session in the Assembly Hall. Alumni of all generations come together to swap stories and honor the unique experiences that tie us all to South Kent.

Before lunch, don鈥檛 miss the much-anticipated Showcase and Signing of South Kent鈥檚 Centennial Book, “Enduring Foundations”, written by 鈥淔aculty Brat鈥� and beloved author Marge Smith. This commemorative moment celebrates the legacy of our school and the voices that built it.

After lunch and class photos, explore what鈥檚 new with a Tour of North Campus, led by Director Rich Chavka. Then, gear up for an exciting afternoon of athletics:

The Alumni Soccer Game (read more) on Farr Field, led by Coach Brennan and Alex Quinones 鈥�19 is expected have a big turn out and you can find more of your teammates on the .

The Alumni Hockey Game at South Kent鈥檚 indoor rink, led by Coach Belger along with Dillon Duncan 鈥�04 and Rich Brande 鈥�88

And Rowing on Hatch Pond, a serene and nostalgic way to close out the action.

Saturday evening begins with a meaningful Alumni Memorial Service in St. Michael鈥檚 Chapel, followed by the grand finale: the Alumni Dinner and Awards Ceremony, honoring outstanding members of our community and closing theweekend on a high note.

鈥淎lways a highlight of the year, Alumni Weekend delivers each time. The connections and reconnections that people make over the weekend are amazing and stay with you forever鈥� – Rich Brande 鈥�88.

Register Now
With the weekend quickly approaching you can preview classmates attending on the registration page. If you need a place to stay dorm lodging is available, as well as plenty of places in the town of Kent — and you can use our special SKS discounts found here. Please you鈥檇 like to join or attend, and make sure to to let us know if you鈥檇 like to participate in future Networking Events, Pathways Talks, Career Days, and more.

We can鈥檛 wait to welcome you home to the Hillside. See you at Alumni Weekend 2025!
Missed last year’s Alumni Weekend? Check out the Centennial Celebrations from 2024 and post .

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Young Alumni Graduate Workshop Series: Preparing for Life Beyond South Kent

Led by Dillon Duncan 鈥�04 and Rich Brande 鈥�88 from South Kent鈥檚 Young Alumni and Advancement Team, alongside distinguished faculty and alumni, this workshop series will provide essential insights, tools, and connections to support you in your post-graduation journey.

The morning workshop will feature five interactive sessions each crafted to equip you with the tools to stay connected, build your professional network, and carry forward the values instilled during your time on the Hillside.

As we celebrate 101 years of exceptional graduates, South Kent remains deeply committed to fostering lifelong connections between our students and the alumni network. This upcoming event is designed to strengthen those bonds by focusing on professional development, networking, leadership, and continued engagement with your soon-to-be alma mater.

For student , or Alumni looking to participate in mentoring event like these please contact Lara Barrett.聽

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