Late in Amber Dermont’s first novel, “The Starboard Sea,” families gather for parents’ weekend at a New England boarding school. It’s the fall of 1987; Black Monday has gutted portfolios around the world; and a hurricane recently ripped out a couple of giant elms that once loomed over the campus.

“We’ve got to fill up the holes,” the headmaster says at a reception, and a parent ceremoniously flips a $20 into one of the craters, sparking a trend only The Donald could love. “As parents joined and left the party, a spirit of giving developed and more bills were added until both holes were covered in a fresh turf of green money,” Dermont writes. “No one bothered to collect the donations.”

“The Starboard Sea” offers a revealing glimpse into the world of the 1 percent. It reminds us how greed and pride lead to moral bankruptcy, how money and privilege insulate the rich from risk. At the same time, it’s also a portrait of teenage love, the exquisite pain of grief and regret, and the exhilarating world of competitive sailing.

The narrative follows Jason Prosper, the son of a wealthy Manhattan banker, through his senior year at Bellingham Academy, a school of last resort for misfit trust-funders who’ve been expelled from elite institutions. Or, as Jason puts it, “Bellingham Academy: everything you always wanted in a prep school and less.”

When he gets to the campus, Jason is mourning the suicide of his best friend and former sailing teammate, Cal, but it’s not long before he develops an intimate relationship with ­Aidan, an enchanting bohemian classmate who has Fred Astaire’s tap shoes “suspended in midstep” above her shelves and a golden fleck of broken glass lodged in her eye. But just when it looks as if Aidan might ease Jason’s pain, she turns up dead the morning after that hurricane. It’s ruled a suicide, but Jason’s not buying it, and he sets out to uncover the truth.

A graduate of the Tabor Academy, a selective Massachusetts prep school that hugs Buzzards Bay, Dermont draws the tony campus life in “The Starboard Sea” with an insider’s hand. The headmaster’s voice ricochets around the chapel like a “well-served squash ball,” and Jason complains that going to Bellingham was “almost as bad as ending up at Choate.” On a cold morning, one of Jason’s classmates is mocked for offering a friend his scarf — “the slightest kindness a sign of weakness.”

Dermont is a seasoned sailor, and readers in Annapolis will get a charge out of her exact, salty depictions of rigging, knots and nautical gear. She also writes vividly about the strategy of sailing. Jason evinces a Gretzkylike approach to reading the wind: “It’s not enough to know where the wind is,” he says. “You also have to anticipate where it’s going to be.” Later in the novel, he describes how a sailor can use seiche — the way water pools and rolls on a lake — to edge out opponents in a race. “It’s like the way water moves in a bathtub when you stretch back or move your legs.”

One of the most refreshing aspects of the novel is Dermont’s candid treatment of race. Through the character of Chester Baldwin, a black student who chose Bellingham for its top-ranked tennis team, she reminds us that money can’t buy pedigree. “My dad, he’s built his life around the idea that there’s this thing called justice,” Chester says after suffering a brutal, racially motivated attack from his classmates. “I know better. If I told [the administration], nothing would happen to Tazewell’s crew. But my life would be ruined.”

Jason has been compared to Nick Carraway for his sober narration and keen sensitivity to the decadence of his peers, and in more than a few instances “The Starboard Sea” feels like a distant cousin of “The Great Gatsby.” But never do the two resemble each other more than when Jason’s mother, concerned over her elder son’s reckless pursuit of wealth, offers Jason this gem: “Your brother knows the price of everything and the value of nothing.”

As long as we remain the status-obsessed, money-hungry society we are, words like those will always bite.

Wilwol is a writer living in Washington.
Michael Dirda will be back next week.


By Amber Dermont

St. Martin’s.
310 pp. $24.99