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The Crossword Puzzle Master

Determination and a good vocabulary made Will Shortz a full time crossword puzzle professional.

A Peculiar Talent

Awful! Worse! Wham! Damn! Will Shortz is at it again, volubly criticizing himself as he wins yet another game at a table tennis club in Westchester County, New York. Five years ago, he was mediocre. Today he's one of the country's top Ping-Pong players in the over-50 category.

Shortz's unique, twist-of-the-wrist slamming seems a far cry from his even more unusual day job as the crossword puzzle editor of The New York Times. But in his view, "the two games are heads and tails of the same coin. Both are confined to a small space. Both involve strategy and guile. Both drive you obsessively to excel."

The Indiana kid started out as a straitlaced Hoosier, a bookworm who got his thrills from words. "I was a nerd back then," he admits, "but that's hardly a put-down. I say it with pride." What other kid lapped up books with titles like Language on Vacation: An Olio of Orthographical Oddities? "This is the classic work on logology, the study of wordplay," Shortz explains. "And I devoured it."

At 14, he wrote the author, Dmitri Borgmann. "I asked if he thought I could make a living as a puzzle maker. He wrote me a very nice, long reply saying, basically, no."

That didn't stop Shortz. Encouraged by his mother, a children's author, he sold puzzles to a kids' magazine and kept on selling them while attending Indiana University, where he made an epochal decision. "The university allows students to create their own major," Shortz says. "And ransacking a dictionary, I found just the word I wanted for my thesis: enigmatology, the study of puzzles."

The enigmatologist graduated cum laude and went on to law school, but his heart just wasn't in it. "I started law school with the idea that I'd practice law for ten years, make a lot of money, and then retire to do puzzles," he says. "But then I thought, Why should I spend ten years of my life doing something I don't love?"

Follow Your Bliss

Leaping off the legal career track, Shortz landed a low-paying job at a crossword puzzle publication before becoming an associate editor at Games magazine. As he points out in Wordplay, the 2006 documentary about him, "I never got into crosswords to make money. I always thought if I could do what I wanted to do, I would live a life of genteel poverty, but I would be happy."

Genteel poverty ended for Shortz in 1993 when, after having risen to the post of editor at Games, he fielded an offer from the Times to edit the paper's crossword puzzle.

The Times crosswords were then rather stodgy affairs, filled with classical references and formal phrases. Under Shortz, puzzles began to draw on names of rock groups and companies like Exxon—"sounds and sights that people encounter in everyday life." The editor became famous for unexpected linkages of new words and old ones. The answer to the clue "digital monitor" was "manicurist," and "hard drive" led to the solution "Tiger's tee shot."

All this has added up to celebrityhood for the man who wears the nerd label so proudly. His legions of puzzle groupies include President Bill Clinton, TV host Jon Stewart, Yankees pitcher Mike Mussina and the folk rockers Indigo Girls. Two years ago, the website gawker.com named him No. 1 Hottie at The New York Times in the "Love Him for His Brain" category.

A confirmed bachelor, Shortz, 55, can be found after work, as often as six nights a week, looping and lobbing. Question his schedule and he replies, "Seems logical to me. I can see myself doing the same things at 90, maybe drooling and confined to a wheelchair, but still turning out puzzle clues and slamming away."

Then he excuses himself to attend to business: Awful! Worse! Wham! Damn! The magnificent obsessive is back on the grid again.
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