Go, Socrates!


Three personal routes to what the Guinness Book of World Records once ranked as the planet’s most expensive prep school—a school, however, that remains a Connecticut secret:

Brad Allen arrived in September 2011 with, among other possessions, a sackful of guilt. He had grown up as a child of privilege in Greenwich. He and his twin brother, Tyler, admired their father’s achievements as owner of a private equity firm, but though his brother was eager to go to college, to succeed like their father had, Brad had no such motivation.

He felt lost at Greenwich High. Though it has been consistently ranked high nationally among public high schools, Brad found it too big, too impersonal and uninspiring. “I wasn’t motivated,” he says. “I wasn’t hunkering down. I wasn’t doing the work.”

None of the curriculum, he decided, would be of use in future employment at a gas station, or playing in a band. He knew he was disappointing his parents but had no answer for them, until a buddy—a fellow underachiever—told him of his own discovery up Interstate 95, just an hour or so away.

Brady Agovino’s academic record at Greenwich High had been even worse than Brad’s—“I was a D student, terrible in every way,” he says. “I wouldn’t do homework. I was not listening. And I had learning disabilities.” These included ADHD and dyslexia. All around him on the Gold Coast he saw success—heads of corporations and other prominent residents, living in manors, driving foreign sports cars. “But I was given a piece of paper, a diagnosis, that told me I was not able,” he says.

He was so convinced of this that he dropped out of school. “I hung with friends,” Agovino recalls. But he also did some soul-searching. “After I turned 18, I woke up one day and said to myself, ‘This is not okay with me. This is not the way I want to live my life. I know I have way too much potential to do nothing. I know I’m here for a reason.’”

And so he searched the Internet for a school that would give him what he needed. He was surprised to find one in Westbrook, a school where the ratio of teachers to students was 1:1. How could that kind of math even be possible?

Jaleel Martin would also have been an ideal candidate for such a place, except for the bothersome detail of the $54,900 needed for a year’s tuition, room and board. Jaleel grew up in Manchester and Hartford, the son of a father who abandoned the family and a mother who had to work very hard to provide shelter and food. As the oldest of her children, Jaleel was given the responsibility to make sure the others did their homework and stayed out of trouble. Perhaps the responsibility wore on him.

“I had anger issues,” Jaleel recalls. Once a promising student, he saw his grades plummet. “I felt like I was retarded. I was shy.”

His report cards, which he hid from his mother, were dreadful. “How I passed my junior year, I don’t know.” And then something kicked in. “I realized that my mother had been busting her behind to make sure I got to school, and how much I had disappointed her. Being the oldest of her children, I wasn’t setting an example for the others.”  

Jaleel worked harder in his senior year. He also volunteered with the Hartford Boys and Girls Club, helping in food drives and aiding the homeless, and was named the club’s Youth of the Year. But even though he graduated from Hartford’s Weaver High last spring, he says, “I realized I still wasn’t ready for college.”  

His volunteer work, however, had led him to a job at the prestigious Hartford law firm of Robinson & Cole as an intern in the mailroom. While he was there, one of the lawyers suggested he look into a school called Oxford Academy, where he could do a post-grad year and prepare for college. But how could he go without a scholarship? Oxford had never granted such gifts.

The school was founded in Manhattan in 1906 by Dr. Joseph Weidberg, whose idea was that, for a variety of reasons, some very smart boys seem to fall through the academic cracks. He believed in the Socratic Method—asking and answering questions to stimulate critical thinking, and doing this intimately, one-on- one. The school was clearly aimed at parents with means. Over the years, his academy prospered, first in the city and then in New Jersey, where a campus was built.

In 1971, however, a fire caused major damage, and school leaders decided to rebuild in Westbrook, on a 14-acre site that borders both the Boston Post Road and Long Island Sound —a gorgeous setting for a campus that by design would never be home to more than 48 boys for a school year, all of them able to pay their way. Boys came not only from the region and nation, but from Kuwait, Germany, Korea and many other countries.

Oxford is no longer the world’s most expensive prep school, though it still costs more to go there for a year than, say, Kent School, and even Yale is a tad cheaper. But headmaster Philip Cocchiola and the board were eager to make Oxford an option some for boys whose families couldn’t pay. Through fundraising and grants, the school’s first scholarships were created—and that’s how Jaleel Martin came to Westbrook.

I visited the campus on a bright autumn day. At the time, there were only 29 students enrolled, not unusual for the early months of the school year. By January, that number will begin to approach the maximum, as other schools identify boys who need this kind of academic attention and responsibility. Indeed, though the school remains largely unknown to the public (something the administration would like to change), guidance counselors and educational consultants know it well.

My tour of the campus took me through the library, dorms, art room, classrooms and soccer field. Just two days earlier, the varsity soccer team had lost a game to a bigger school (every opponent is a bigger school), but two days before that, it had actually won a game, and Jaleel had been one of the stars. Not that being a varsity player gives a boy elite status here. There are no tryouts, and the team is composed of nearly half the present student body.

It’s all a very tight group, and most students are eager to talk about their academic discoveries. Brad Allen, for example, found in Ayn Rand’s protagonist Howard Roark a meaningful role model. Brady Agovino shocked himself and his parents when, after his first semester at Oxford, he brought home a 4.0 average. Jaleel Martin is now, according to his headmaster, one of the best students in the school. All three plan to go to college.

They could all be inspired by the path of John Filippelli, a 2006 alumnus of Oxford, who, back in his days of growing up in Greenwich as an undistinguished student, would never have imagined graduating from Fordham University or working as he now does for CBS News. Anchors now rely on him to help report on a complex world—a world that was introduced to him by Socrates, and by teachers who stared him in the eyes in a small classroom in a place up the coast that almost nobody knows.

Go, Socrates!

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