The Classmates: Privilege, Chaos, and the End of an Era

by Geoffrey Douglas

Fifty years ago, in the fall of 1957, two thirteen-year-old boys were enrolled at an elite, boys-only New England boarding school. One of them, descended from wealth and eminence, would go on to Yale, then to a career as a navy officer and Vietnam war hero, and finally to the U.S. Senate, from where he would fall just short of the White House. The other was a scholarship student, a misfit giant of a boy from a Pennsylvania farm town who would suffer shameful debasements at the hands of his classmates, then go on to a solitary and largely anonymous life as a salesman of encyclopedias and trailer parts--before dying, alone, twelve months after his classmate's narrow loss on Election Day 2004.

It is around these two figures, John Kerry and a boy known here only as Arthur, the bookends of a class of one hundred boys, that Geoffrey Douglas--himself a member of that boarding-school class--builds this remarkable memoir. His portrait of their lives and the lives of five others in that class--two more Vietnam veterans with vastly divergent stories, a federal judge, a gay New York artist who struggled for years to find his place in the world, and Douglas himself--offers a memorable look back to a generation caught between the expectations of their fathers and the sometimes terrifying pulls of a society driven by war, defiance, and self-doubt.

The class of 1962 was not so different from any other, with its share of swaggerers and shining stars, outcasts and scholarship students. Its distinction was in its at the precise threshold of the cultural and political upheavals of the late 1960s. The world these boys had been trained to enter and to lead, a world very similar to their fathers', would be exploded and recast almost at the moment of their entrance--forcing choices whose consequences were sometimes lifelong. Douglas's chronicle of those times and choices is both a capsule history of an era and a literary tour de force.

Genres: Current Affairs, Memoir

256 pages, Hardcover

First published January 1, 2008

About the author

Geoffrey Douglas is the author of six books --five of nonfiction and one novel--and more than 100 magazine pieces, many of them widely anthologized. A former reporter, editor, columnist, and adjunct professor of creative writing at the University of Massachusetts, he has been a fellow at the Bread Loaf Writers Conference and a writer-in-residence at several schools and universities.
His most recent work, "Love in a Dark Place" (2025), described by Kirkus Reviews as "a moving, unflinching novel about human depravity and the way love can coexist in its menacing presence," is set in 1980s Atlantic City, where Douglas worked at the time as editor of an investigative weekly.
Other books include two widely-reviewed memoirs -- "Class" (1992) and “The Classmates" (2008) -- as well as "The Game of Their Lives “ (1996), an account of the 1950 U.S. World Cup soccer team and the immigrant men who composed it, adapted as a 2005 movie of the same name. His fifth book, “The Grifter, The Poet, and The Runaway Train: Stories From a Yankee Writer’s Notebook" (2019), is a compilation of his stories in Yankee, written over 20 years.

Reviews

[Jim · Rating 3 out of 5]

A well-written and short to-the-point book (published in 2008). It's a story about boys enrolled in an elite New England boarding school (needless to say, it was boys-only at the time). What made it most interesting was that it was about the class of 1962, who would face the upheavals of the 1960s, especially the Vietnam War. Author Geoffrey Douglas was among the students and he recounts what life was like at the school and what happened to some of his classmates afterwards. He himself didn't graduate from the school and his life took many twists and turns before he became a published writer and an adjunct professor of writing.
Douglas did not go into the military, but others did. One was an outsider of the class (as Douglas himself was), who went on to Yale and then became a Navy officer, commanding a swift boat in Vietnam. Much later, this former classmate ran for President of the United States (in 2004) winning 59,000,000 votes. This was, of course, John Kerry. Douglas was able to interview Kerry for this book but, unsurprisingly, he failed to make a real connection with Kerry. The man was stiff and aloof, still having those same qualities he had had as a boy and which contributed to his defeat in the election.
Douglas writes about several of his classmates. One went on to become a judge and have a seemingly perfect life. Another felt he could not live up to the great expectations placed upon him and became an artist (and came out as gay, something he would never have done as a student). And, most sadly, there was the scholarship student, a big socially awkward Pennsylvania farm boy. "Arthur" did not fit in at all with the other students, who had elitist and privileged backgrounds. He would suffer shameful debasements at the hands of his classmates and go on to lead a solitary life selling trailer parts. He would die a year after his classmate's loss on Election Day 2004.
"The Wall Street Journal" calls this a " perceptive piece of social history" and I agree. It was of most interest to me as a person who grew up during the 60s. When I graduated from high school, it was 1970 and the drawdown of US forces in Vietnam was underway. I had little fear of having to go to Southeast Asia and I went on to college and to have a career as a teacher, a very different story from that of John Kerry and so many others who were just a little older...

[James Henderson · Rating 4 out of 5]

I enjoy reading memoirs, and my enjoyment is increased if, as in this case, the memoir is contemporaneous with part of my life. While I did not go to an elite private school in New England like this author, I was in high school just a few years later experiencing some of the small and large events in my own place and way.
This memoir was triggered, in the spring of 2004, by the presidential bid of fellow alum Kerry, and its impact on some of his former classmates at St. Paul's school more than forty years earlier. The author recalls the frantic e-mail exchanges that eventually prompted him to meet with a few of his former classmates, including Kerry. He discovered that St. Paul’s alumni had endured a broad range of experiences since graduating, and he eloquently chronicles those experiences. The narrative frequently returns to Arthur, a class clown mercilessly ridiculed at school who suddenly died while the e-mail reunion was in full swing. The book is filled with the emotions unleashed by a group of middle-aged men’s miraculous reconnection. Douglas describes meetings between himself and several other graduates, including Chad Floyd, a successful architect and Vietnam vet whose wife was crippled by depression, and Philip Heckscher, a Harlem high-school teacher who took a long time coming to terms with his homosexuality. While the discussion about John Kerry is the least interesting in the book it matters little, because the reunion he inadvertently sparked opens a gateway for Douglas to muse on his own life journey, one that began with his leaving St. Paul's a year before graduation, and such larger concepts as identity, loss, expectation, failure and idealism. This memoir brought back my own memories of not too dissimilar events and interactions with my fellow high school classmates, some of whom I reconnected with last fall at our high school reunion. Douglas' memoir is among the best I have read.

[Nancy · Rating 4 out of 5]

I really enjoyed The Classmates. These boys were in prep school and most graduated just before the 1960s before the race riots and Vietnam and the assassinations of John and Robert Kennedy and Martin Luther King.
They entered a world very unlike the one they had grown up in and for which they were largely unprepared.
One of the classmates in this New England all-boys boarding school was John Kerry, but Kerry does not figure very much in the book until a chapter at almost the very end of the book.
Douglas describes some of the boys he went to school with and follows some of them through their adult lives. He records personalities and ambitions and life choices. It cannot help but make you think of the classmates from your own school, and many sound very familiar.
The chapter on Kerry is far from boring, and holds clues to Kerry's personality and why he lost his bid for president against George W. Bush. A very satisfying read.

[Christina · Rating 3 out of 5]

the theme of privileged kids being prepared for a world that disappeared reminded me of one of my all-time favorites - "the education of henry adams." interesting parallel between the two, given that the adams book was written more than a century before. Classmates is overly sentimental in parts and I think Douglas was unkind to John Kerry, in part because Kerry wouldn't give him what he wanted. Interesting and enjoyable overall.

[Kristine · Rating 3 out of 5]

Geoffrey Douglas was a classmate of John Kerry at boarding school in the late 1950’s. When Kerry was running for president in 2004 “the form” got in touch again and stayed in touch, and the story proceeds from the fact that they graduated from a privileged educational position just in time for the 1960’s to ignite. Their personal histories are thus part of a historical moment, not just their personal histories, I get that; but the story dragged through his efforts to get in touch with these people and write his self-important book about them. By the end it seemed just
meanspirited covered with an elaborate shrug: John Kerry never really cooperated with him, dammit, and he’d done him the huge favor of writing a book about him even though he lost the election.

[Scott · Rating 5 out of 5]

Igby Goes Down meets Old School. I didn't go to a private school, but this guy and I both left Columbia, and both drank at the Gold Rail bar. I know this guy and his friends. Great book.

[Shannon Warfield Hayes]

It's slow ...

[Meredith · Rating 3 out of 5]

Preferred Tobias Wolff's Old School, but still an interesting read, especially with the John Kerry connection.

[David · Rating 3 out of 5]

I thought this was a sad and empty book. And maybe one that would have been better written by a classmate.

[Karen · Rating 5 out of 5]

This was a book that I could not put down. Heartfelt and insightful. I could so indentify with the story as Geoffrey went to a New England boarding school, not unlike St. Paul’s. His experiences are from the 1970s, but the themes are the same. There was great loneliness, humor, exclusion, inclusion, inspiring teachers and learning to be responsible (too much is given, much is expected) and the universal quest in trying to find one's place in the world. The life experience at a boarding school seems to be amplified when you are away from your family support system and you are much on your own. Geoffrey was 8 years old when he was sent away to school – it forever changed him, for better or worse.