For 21 years, Allan Calhamer walked a mail route in La Grange Park, the town where he had grown up and graduated from high school, where he had chosen to settle down and raise his two daughters. He was a tall, soft, abstracted man, who examined the world through thick, scholarly glasses, and went home at night to study history. No one noticed those distinguishing details under the blue uniform, the patch that read “Letter Carrier.” Suburban mailman is a job that guarantees anonymity, and that’s exactly what Calhamer found on the sidewalks of his hometown.

Outside La Grange Park, though, Calhamer wasn’t anonymous. As a young man—one of the brightest young men the town ever produced—Calhamer had gone away to Harvard. In the early fifties, while still an undergraduate, he invented the board game Diplomacy. A thinking man’s version of Risk, Diplomacy invites players to take the role of a great power in pre–World War I Europe, and negotiate, cajole, wheedle, and backstab their way to continental domination. Since it was published in 1959, the game has sold more than 300,000 copies. John F. Kennedy played it in the White House. Henry Kissinger played it to hone the skills that would make him secretary of state. As simple to learn as chess and as difficult to master as mergers and acquisitions, Diplomacy has an obsessive following, from the local club Windy City Weasels to an international tournament circuit and webzines that publish articles such as “Rethinking Russia’s Opening Strategy” and “The Belgian Gambit.”

Diplomacy was a pioneering war game—“one of the early signs of organized gaming,” according to Derk Solko of the Web site Board Game Geek. But it never made Calhamer rich—he once bought a Mercury Monarch with the royalties—and it led him astray from the career path most Harvard men follow. After inventing the game, he drifted through an aborted stint at Harvard Law, a few months in the foreign service, a career as a systems analyst. In the late sixties, living on welfare in New York City, he took a job as a guard at the Statue of Liberty.

“It might have been bad in a sense,” Calhamer, 77, says today of Diplomacy. “It might have been a distraction to my conniving my way up.”

For one great achievement, was it worth it?

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Illustration: Sean McCabe

Diplomacy’s origins go back to Calhamer’s boyhood in La Grange Park. Bookish and ungainly, he spent his days indoors, playing chess and All-Star Baseball, a game that used a spinner to simulate major-league contests. World War II broke out when Calhamer was eight, and he avidly followed the news with his parents.

“His mother encouraged him to have a big imagination, and he was always inventing board games,” remembers Gordon Leavitt, a childhood playmate. Calhamer loved military history: “Allan had a toy rifle, and he learned the manual of arms from World War I. He was really hep on that.”

One day, rummaging in the Calhamers’ attic, the boys discovered an old geography book. Calhamer was fascinated by the exotic, bygone countries on the maps: Austria-Hungary, Serbia, the Ottoman Empire. “That was the seed of the game,” Leavitt says.

After graduating from Lyons Township High School, Calhamer and Leavitt both won scholarships to Harvard. In the late forties, the college was still all-male, and Calhamer fell in with a group whose social lives revolved around board games. He played on the chess team and conceived a three-dimensional version of tic-tac-toe.

“None of us were outgoing socially, none of us were dating at the time, so instead of going out, we played games,” says Stuart Dreyfus, later an engineering professor at the University of California–Berkeley.

Dreyfus remembers Calhamer as a brilliant iconoclast who broke every principle of campus conformity. In liberal Cambridge, Massachusetts, he was a young Republican. At the same time, he dabbled in modern art, dipping eggbeaters into buckets of paint and splattering canvases.

Calhamer was a history major, and a class in 19th-century Europe furnished the final inspiration for Diplomacy. The professor had written a book called Origins of the World War. Reading it, Calhamer recalled the atlas in his family’s attic. “That brought everything together,” Calhamer says now. “I thought, What a board game that would make.”

Excitedly, he traced a map of Europe, circa 1900, and recruited six game-playing friends. The rules were simple: Each country starts with three “supply centers” and three pieces, except for Russia, which has four. The object: Occupy half the centers on the board. No country was strong enough to do that on its own, so players had to form alliances. But only one country could win, so eventually, someone had to turn on an ally.

Diplomacy was a brilliant simulation of international relations. The most vulnerable countries were the centrally located Germany, Austria, and Italy. As in real life, they often banded together against the surrounding powers. But the game also featured a cunning look at interpersonal relations. Playing the other players was as important as playing the pieces.

“It’s about getting people to do what you want them to do, and convincing them it’s to their benefit,” says Doug Kent, who runs the magazine Diplomacy World. Critics of Diplomacy consider it a cynical exercise in deception. “I call it the Friendship Wrecker,” says Solko, of Board Game Geek.

Even Calhamer admits Diplomacy wasn’t a dorm-room hit. It was hard to gather seven guys to represent France, England, Germany, Italy, Austria, Russia, and Turkey. And his introverted pals were not natural politicians.

“Only his best friends condescended to play,” says Dreyfus, who never enjoyed the game because, he says, “I’m completely honest.”

After college, Calhamer was classified 4-F, or ineligible for military service, because of diabetes. So he tried Harvard Law School. Law students loved the game, gathering in Calhamer’s attic apartment to practice dealmaking.

“Lawyers like Diplomacy because they’re into power,” says Leavitt. “Double-crossing people comes naturally to them. Allan had the wrong kind of personality to become a lawyer. He wasn’t aggressive enough. He’s more scholarly.”

Calhamer dropped out of law school after a year and a half. Trying to put his interest in diplomacy to work, he took the foreign service exam, but that yielded only a three-month temporary assignment in Africa. When he returned to the United States, Calhamer felt encouraged enough by his classmates’ interest in Diplomacy to make 500 copies, which he sold through toy stores in New York, Chicago, and Boston. It looked as though the game might finally be his ticket. The board game colossus Avalon Hill bought the rights, giving Calhamer a five-percent royalty payment on each sale, and Diplomacy became an international smash.

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Photograph: Megan Lovejoy

“The Kennedys are said to play it at the White House, and I understand the Western Alliance is demanding early assurances that Jack sometimes wins,” a columnist at the London Evening Standard reported.

Sylvania, the defense contractor, was so impressed it offered Calhamer a job in operations research, hoping he would develop a program based on his game. But Calhamer never took to corporate life: Deep down, he saw himself as a game inventor, harboring the hope that Diplomacy would rescue him from a desk job.

Despite its success, Diplomacy’s royalties were never enough to provide Calhamer with a living. He left Sylvania after six years and ended up on welfare while he looked for a computer-programming job in New York. While “drifting around hither and yon,” he met his wife-to-be, Hilda, a Dominican immigrant. That’ll focus any guy on work. Calhamer ran out and got a job at the Statue of Liberty. When he took Hilda to La Grange Park, she fell in love with the quiet, arbored suburb. So Calhamer brought her to his home and settled down to life as a postal worker.

“That proved to be pretty worthwhile,” he says. “It doesn’t sound like a high-level job, but it was completely reliable, and it paid. I was pretty good at sorting mail. You have to be accurate.”

In any case, Calhamer’s claim to fame was secure. He wouldn’t always be a mailman. He would always be the inventor of Diplomacy. The game has outlasted its imitators—most military strategy games were unwieldy monstrosities with thick rule books and hundreds of pieces—and transcended the war-game genre it helped create. Games magazine named Diplomacy to its Hall of Fame, along with such rainy-day classics as Monopoly, Scrabble, Clue, Yahtzee, and Sorry! On a visit to the State Department in Washington, Calhamer was a celebrity, sought out by generals and undersecretaries. In the sixties and seventies, he competed in Diplomacy tournaments, although he wasn’t one of the more successful players, says Edi Birsan, a veteran gamer from the San Francisco area.

“He doesn’t take into account the personalities of the players,” says Birsan, noting that game inventors rarely master their own creations. “His personality is such that he’s not an aggressive communicator.”

(“I think I play it fairly well,” Calhamer says, pointing to several tournament victories. “I try to offer deals that are good for both sides and are self-regulating.”)

It’s not surprising to hear the inventor of Diplomacy called a poor diplomat. It could be that Calhamer incorporated something he lacked in life into the fantasy world of the game. The inventor of Monopoly, after all, was stone broke.

Gordon Leavitt, now a retired actuary in New York, seems disappointed at how things turned out for the neighbor kid who was so fascinated with armies, maps, and World War I.

“He should have been a history professor,” says Leavitt, who nonetheless nominated Calhamer for the Lyons Township High School Hall of Fame. He never heard back. “They didn’t understand what he’d done. They’re used to corporate vice presidents. ‘Game inventor? What’s that?’ If somebody had written a book that’s still in print 50 years later, that’d be quite an accomplishment. That’s what Allan did. He invented something that’s still being used 50 years later.”

Dreyfus is less surprised by his classmate’s path. Calhamer was never interested in money, power, or public approval. A better businessman might have gotten rich off Diplomacy. As it is, Calhamer’s old age is made comfortable by a family inheritance.

“He did that consciously,” Dreyfus says. “I think he wanted his own time. I don’t think he wanted to work for any immediate boss.”

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Before the Harvard class of 1953 gathered for its golden reunion, a questionnaire went out to every member. Asked his most important professional achievement, Calhamer responded, “Invention of the game Diplomacy.” Asked what he would have done differently with his life, he gave an answer you probably won’t often hear from a Harvard man: “I probably would have done everything differently.”

Calhamer missed out on the material rewards of an Ivy League education—the partnership, the private club, the summer house, the sailboat. The unconventional mind that created a landmark board game was never suited for a conventional career. But Diplomacy clubs will still be meeting after his classmates’ lawsuits and lectures are forgotten. He may have some regrets about the course of his life, but he has a legacy. Asked which life he would have preferred, Calhamer taps a copy of his game.

“It’s better to have this,” he says. “It makes you feel like you did something.”