Jean Charles ’83: A Baton Received and Passed

Enduring Gratitude

Jean Charles '83 and family

Jean Charles '83 with his wife, Lynn, and daughters Maxine and Sydney.

Read the Fall 2023/Winter 2024 Hotchkiss Magazine

By Eliott Grover

From a young age, Jean Charles ’83 learned how to identify and embrace opportunities for advancement. Since then, he has made a point of creating chances for others.

The letter arrived when he was 14. Jean Charles ’83 had never heard of The Hotchkiss School, yet there he was holding a formal offer to attend. Hotchkiss had received his file from A Better Chance (ABC), a nonprofit that partners with independent schools to create opportunities for historically underrepresented students.

“I accepted it sight unseen,” Charles says.

At first, his mother was reluctant to send her youngest son to boarding school. “My dad was kind of like, ‘Well, it’s an opportunity. If he wants to do it, let him do it,’” Charles says. “Because what you don’t want is to regret later on that you didn’t try.”

Although living away from home was a daunting prospect, Charles drew inspiration from his family. “My parents had left a tumultuous situation in Haiti and emigrated to Africa,” he says. “To me, they already set an example of being intrepid.”

In 1964, two years before Charles was born, his parents decided to leave Haiti after François Duvalier declared himself “president for life.” This explicit display of autocracy occurred around the same time that many African nations were gaining their independence. Many of these countries sought to grow their educated civilian populations through immigration.

“A lot of people who were educated in Haiti took that opportunity to come over to Africa as teachers,” Charles says. “My dad was a lawyer in Haiti, but given the political circumstances, he took the opportunity to be a teacher in Zaire.”

It was not an easy decision for his parents. They had to leave their four oldest sons in Haiti under the care of relatives, but they believed it was in the best long-term interests of the family. Their two daughters were able to come with them to Zaire, where Charles was born in 1966. They did not stay long. “Their vision for reuniting the family was to emigrate,” Charles says.

When Charles was 2, they moved to the United States. They settled in Queens, NY, and Charles met his brothers for the first time. Growing up, he did well in the public school system and was encouraged to apply to ABC. When he received the letter from Hotchkiss, he sensed its significance. “I can try this,” he thought. “And if I fail, I’m no worse off. But who knows, maybe this opens up a whole different world.”

Jean Charles '83

Finding a Strong Sense of Self and Purpose at Hotchkiss

Charles arrived in Lakeville in the fall of 1980. A 98-pound 14-year-old who skipped ninth grade in order to start as a lower mid, he was smaller and younger than most of his peers. Other differences, he says, were just as obvious. He was one of fewer than two dozen Black students on campus. Many of his classmates came from highly privileged backgrounds. “There were kids from some of the most prominent families and name brands that you would hear of––politically and economically,” he adds. “I didn’t suffer from hunger, but I knew we weren’t ballers.”

Adolescence is universally challenging. “I think what makes it so tough is that you’re trying so hard to fit in, but what makes you special is how you’re different,” Charles says.

While coming of age in an environment with such stark social differences could have made for a particularly trying experience, Charles arrived at Hotchkiss with a strong sense of self and purpose. “Obviously I think I wanted to fit in, but I knew from the jump that I didn’t,” he says. “And I was okay with that. It’s never been a source of distress or lack of confidence for me. In fact, as I’ve become a bit more self aware, I do feel that I’ve always been a part of and apart from almost every aspect of my life. For example, in my own family, I’m the only one who is African. Everyone else is Haitian in terms of where they were born.”

Rather than dwelling on how he was different from other Hotchkiss students, Charles identified key similarities. “I’m a student who has some academic talent who’s here trying to learn and be better,” he remembers thinking. “To me, that’s what I was there to do. If I had an opportunity to make some friends, obviously that makes things easier.” And it did. Charles says his classmates John McLaughlin ’83, Matt Meade ’83, Greg Keller ’83, and Carl Shannon ’83 became close friends and stalwarts for him in dorm life.

Jean Charles '83 on wrestling team

The wrestling team in the 1983 Mischianza. Jean Charles ’83 is in the front row, third from left.

Capturing a State Championship

Charles’s comfort in his own skin allowed him to prioritize his schoolwork while taking advantage of the new opportunities he received at Hotchkiss. His first fall, he was taken aside by a JV football teammate who encouraged him to try wrestling in the winter. It would be an easy varsity letter, the teammate assured him. Because so many schools did not have a wrestler for the 98-pound weight class, Charles could expect to earn forfeit victories in most of his matches. “In the three years I wrestled at Hotchkiss,” Charles says with a laugh, “I think I had one forfeit.”

It might not have been as easy as his friend let on, but wrestling proved to be the perfect sport for Charles. He took to it quickly and forged strong relationships in the process.

Teammates such as the Poggi brothers (Peter ’83, Patrick ’84, P’09,’10, and Paul ’85, P’18,’20) made the wrestling room feel like a sort of home away from home. “Having that family of wrestlers creates a bond because you sweat and shed blood together,” Charles says.

During his lower- and upper-mid seasons, Charles was the runner-up in the state championship. His senior year, the event was held at Hotchkiss and he made it to the final once again. He faced an opponent whom he had defeated earlier in the season, but he had fractured his collarbone in the process and nearly passed out from the pain. In their rematch for the state title, the opponent came out like a ball of fire. “He was very aggressive right from the beginning,” Charles says. “He got the initial takedown to make it 2-0, but he shot his shot and kind of exhausted his energy.” The rest of the match was not close. Charles dictated the tempo and captured the championship in front of his parents and scores of cheering Bearcats.

Unlocking His Potential

In the classroom, Charles credits Hotchkiss with molding him into a strong writer. Through the daily theme assignments, he learned how to structure his compositions effectively to achieve a variety of rhetorical purposes. Across all subjects, Charles says Hotchkiss provided a rigorous yet caring environment that helped him unlock his potential. “The curriculum is challenging, and the teachers are invested in your doing well.”

One Saturday night, Charles was walking through Main Building when he encountered legendary English instructor Robert Hawkins sitting quietly in a chair. Hawkins looked up and said, “Hey, Jean.” Charles was dumbfounded. Hawkins taught exclusively prep students, and since Charles started as a lower mid, he was shocked Hawkins knew his name. He sat down, and they had a conversation. Hawkins shared how the faculty had talked about Charles at their last meeting, as they talked about all students. Hawkins was impressed by what he had heard and was rooting for Charles’s continued success. “You always have these little angels looking out for you,” he says. “When I started having the opportunities to contribute, that’s always been my mindset.”

Jean Charles '83

Helping Others Through Entrepreneurship

After earning degrees from the University of Pennsylvania and Stanford, Charles went into digital marketing. In 2000, he co-founded DrJays, an online clothing retailer that specialized in urban apparel. Although Charles had no fashion experience, his entrepreneurial instincts paired well with the dawn of e-commerce. “One of the things we recognized was there was this huge appreciation for hiphop culture,” he says. “While the interest was global, the accessibility was kind of limited to urban areas, so our thought process was, ‘How do we take that thirst and quench it worldwide?’”

Beyond growing and operating a successful company, Charles takes pride in the number of promising young employees he recruited and mentored during the nearly two decades he ran DrJays. Since leaving in 2018 to start WSI Vital Marketing, a boutique digital marketing firm, Charles has continued to seek avenues to be active in his community while helping others. “I don’t want to sound super corny about it,” he says, “but it’s just a question of if you’ve been blessed or handed a baton, when do you have a chance to do the same?”

Establishing a Scholarship and Passing the Baton

The opportunity Charles received to attend Hotchkiss came in the form of the Frederick S. Jones Scholarship, an award named after the longtime Hotchkiss trustee and former dean of Yale College. It was established by gifts from parents of scholarship boys at Hotchkiss during Jones’s years as president of the Hotchkiss Board of Trustees. In 2007, Charles established the Jean P. Charles ’83 Family Scholarship, a financial aid award for students from underrepresented and minority backgrounds.

“It’s targeted for kids who need it,” he says. “Notwithstanding recent news about affirmative action and diversity, equity, and inclusion, I think we live in a multifaceted world. It’s a lot more instructive when you have direct exposure to that, so you have a better understanding and better communication. If there’s anything I would ask, I would ask people to contribute more to things that are about scholarship––and contribute more specifically for minority scholars, because there’s an opportunity.”

Charles is appreciative of the chance he received to attend Hotchkiss and hopes his gift will create similar opportunities. “I think a lot of good things happen,” he says, “because a lot of good things are already in place.”

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