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Even if you don’t know Will Shortz’s face, you’ve likely spent many a Sunday morning with him -- and countless plane, train, and car rides too. As the crossword editor of the New York Times, he keeps millions of Americans guessing.

IT COULD HAPPEN TO YOU: You’re on a jet to Europe or a train to Boston, struggling with a crossword puzzle, when the pleasant-looking man with the brush mustache in the next seat leans over and introduces himself. “Hi,” he says. “I’m Will Shortz.”


Just the idea that Will Shortz might be looking over your shoulder is enough to make a puzzler break a sweat. That’s because among the millions of Americans who dote on puzzles, Shortz is king. He’s the veteran crossword editor of the New York Times, the first and only puzzle master of National Public Radio’s Weekend Edition Sunday, and the editor of hundreds of best-selling puzzle books. He’s a one-man brand, a living legend in the puzzle world, yet he can pass through a crowd -- or occupy the next seat -- unrecognized. Shortz likes it that way.

Aside from the occasional trip to a national or international puzzle event, Shortz is very much a homebody. His base of operation is a modest 80-year-old English Tudor-style house in the village of Pleasantville, New York, an hour’s drive north of Manhattan. His days are entirely devoted to puzzles: creating them, editing others’ creations, and solving them simply for the pure joy of it. Lately, he’s been spending his nights playing table tennis at a nearby club. The lifelong focus on puzzles and the more recent obsession with Ping-Pong are, he admits, of a piece. “If I get into something,” he says, “I really want to do it well.”

Shortz, 56, was raised on an Indiana Arabian horse farm and was the youngest of three children. When he was eight years old, his mother once kept him busy by giving him crossword puzzles to solve while her bridge club met. That was all it took. Before long, he was making up his own puzzles and demanding that his family and friends try to solve them. His sister, April Curtis, was in college at the time. “When I came home on weekends,” she recalls, “Will would greet me at the door with puzzles he’d made. After a while, they got too hard to do, and I refused. I never did much like puzzles.”

Shortz was just 14 years old when he sold his first creation to a youth magazine. By the age of 16, he was a regular contributor to a top puzzle publication. In school, he enjoyed taking exams, mostly because they challenged him in the same way puzzles did.

Shortz believes that the enjoyment of testing oneself is a common trait among puzzle fans, as is a strong desire to finish what they start. He explains that in real life, puzzlers are often frustrated by the inability to see things through from start to finish; yet with crossword puzzles, they can. And other forms of brainteasers are no exception. When Shortz was a child and his family would set aside a jigsaw puzzle for the night, he would stay up to work on it. “I couldn’t sleep until it was finished,” he says.

When the whiz kid went to college at Indiana University, he was allowed to structure his own curriculum. He put together courses with such titles as Mathematical Puzzles and Twentieth-Century American Word Puzzles and became the only person ever to earn a degree in enigmatology, the study of puzzles. He then enrolled at the University of Virginia School of Law on the assumption that he couldn’t support himself on his puzzle sales alone. He quickly decided he would never practice law. But true to form, he finished what he’d begun and got the degree anyway.

After graduation, Shortz found a job at Games magazine, where he became the editor within a year. During his 15 years there, he had his first encounters with celebrity puzzlers, interviewing famous faces such as Stephen Sondheim, Merv Griffin, and, most memorably, Bill Clinton, who was running for president at the time of their interview. Shortz remembers that Clinton clicked a timer on his watch and began working a crossword puzzle Shortz had brought along. Clinton’s phone rang, he clicked off the watch and answered, and then clicked the watch back on and finished the puzzle as he continued his phone conversation. It was a puzzle of medium New York Times–like difficulty, Shortz recalls, and Clinton completed it in just six minutes and 54 seconds.

But those aren’t Shortz’s only brushes with fame. In puzzling circles, Shortz is something of a celebrity himself, thanks in large part to his founding in 1978 of the annual American Crossword Puzzle Tournament, which he continues to direct to this day and which was featured in the hit documentary Wordplay. Later, Shortz founded the World Puzzle Championship, and he is currently a director of the U.S. team.

In 1987, Shortz was offered the chance to take his talents to the air on National Public Radio. Every Sunday for the last 22 years, he has created a puzzle to present. “Since it’s Sunday,” he says, “I envision the typical listener -- there are almost four million of them -- as half awake or driving to church, so my puzzle can’t be too complicated and can’t require writing.” For example, the question might be, What comes between Thursday and Wednesday alphabetically? (The answer, of course, is Tuesday.)

In 1993, Shortz got the chance of a lifetime when the New York Times -- the gold standard of puzzle periodicals -- conducted a search to find a new puzzles editor. “I ran a competition with four or five candidates,” says Jack Rosenthal, who was then the editor of the Times Magazine, where the puzzles appeared. “The thing that set Will apart was his idea for adding new kinds of puzzles to the puzzle page.” Indeed, with Shortz at the helm, the Times’ puzzles became much more topical, with current events and pop culture added to the list of subjects covered. He also decided to make the puzzles get gradually more difficult throughout the week.

After a decade and a half on the job, Shortz has his routine down pat. First, he chooses which puzzles will be published from the hundreds sent in by freelance constructors -- “cruciverbalists,” as they’re known. Approximately one out of every 10 puzzles submitted makes it to print, but not before Shortz rewrites about half of the clues, which total 32,000 in a year. He checks the accuracy of each clue and solution, and he discards the esoteric words that puzzle-makers too often fall back on. As many as four people go over each puzzle after he finishes it, but inevitably, a handful of errors still manage to creep in every year.

Shortz -- a perfectionist to a fault -- is bothered tremendously by this fact. That’s because to him, puzzles are much more than just time-wasters. He touts them as problem-solving exercises that can replace brain cells lost in the aging process and as low-cost diversions in hard economic times like these. When extolling the virtues of puzzles, Shortz likes to quote the late Margaret Farrar, the Times’ first crossword-puzzle editor: “You can’t worry about where your next rent check is coming from when you’re trying to solve one across and one down.”