Caleb Ockman ’21 arrived at South Kent School 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—and now, just a few years beyond the Hillside, a Fulbright finalist bound for Turkey.
“It started with soccer,” Caleb recalls. “I came to South Kent thanks to Owen Finberg, who helped me understand that this was the place where I could do both—develop as a player and as a student. That was the original goal: play for a top prep team and eventually play in college.”
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.
“The coach who recruited me left before I arrived,” Caleb says. “The new coach had a different style, and it just didn’t click. D3 athletics are intense, but they’re not supposed to be your whole life. I made a tough decision to step away from the team.”
What followed was a flourishing of intellectual curiosity. “Once I left the team, I had time and space to explore,” he says. “I joined the student newspaper and a foreign affairs journal. I started sailing—something I’d never done before—and became a tutor in Russian. I started taking courses that challenged me in entirely new ways.”
Caleb’s interest in Russian wasn’t 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. “He was instrumental in helping me find purpose in the classroom,” he says. “At South Kent, you’re never just a number. People see something in you and help bring it out.”
That ethos—of seeing potential and investing in it—carried 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’s 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—a class on the international relations of Central Asia—would profoundly shape Caleb’s academic and professional direction.
“We studied the region’s geopolitics, from the fall of the Soviet Union to the present, and the role of players like Turkey,
China, and Russia,” he says. “That course made me realize I wanted to pursue a career in foreign policy—and that to understand Eurasia, you can’t just know Russian. You need to understand Turkey.”
That realization sparked his Fulbright application: a proposal to study in Turkey, deepen his understanding of Turkish language and culture, and explore Turkey’s 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—first 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. “It’s a good problem to have,” he laughs. “Both programs are excellent. I’m choosing between different course offerings, housing options, and how far I’ll be from the city center. But either way, I’ll be immersed in a region I care deeply about.”
Though his path began with soccer, it has expanded into a world of diplomacy, cultural fluency, and global citizenship. Caleb
co-founded Williams’ first campus foreign policy group—a 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’s also considering graduate study in law or international relations, though he’s quick to point out that practical experience will come first.
“I want to work. I want to be in the field—whether it’s through the State Department, a federal agency, or a policy institute,” he says. “I care deeply about this region because I grew up there. I’ve 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’s what I want to do.”
From the quiet calm of the Hillside to the complexity of Central Asia, Caleb Ockman’s 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—and a clear vision for the difference he hopes to make.