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The Puzzlemaster’s Dilemma

Will Shortz’s crosswords are about to make him a word-nerd movie star. But Sudoku is making him rich.

Photo-montage by Caroline Shepard  

This is a great puzzle,” says Will Shortz.

The crossword editor for the New York Times is giving me an advance peek at the Sunday puzzle he will publish a week later. “See, now this grid is jam-packed with fresh uses of language,” Shortz says, sitting in his home office amid stacks of reference books like Brands and Companies 1995 and The Encyclopedia of American Cars. “MRPEANUT, great answer. GIJOE, great! Only five letters, yet it has a J in the middle—very pretty.” Shortz has only one complaint about the puzzle: It uses the abbreviation nle for “NL East,” which he thinks is too obscure. It only took him a few minutes to deftly scribble in a new tangle of words. AAMES, of “Willie Aames,” turns into AIMAT; AMMO becomes OLIO; and NLE becomes ULA—a “diminutive suffix,” such as at the end of “spatula.”

Me, I didn’t know ula was a word. But Shortz’s fan base generally does—the millions of word freaks who revere him as the nation’s master of linguistic play. In his thirteen years at the Times, Shortz has revolutionized the paper’s immensely popular crossword. Twenty-five percent of the people who pick up The New York Times Magazine on Sundays flip to Shortz’s puzzle first. This week, his reputation as a word-nerd hero will be cemented with the premiere of Wordplay (see David Edelstein’s review), a documentary that profiles Shortz fans as diverse as Bill Clinton, Jon Stewart, and Yankees pitcher Mike Mussina. They regard his puzzle as the last true showcase for elegant language, sparkling wit, and groan-inducing puns.

Yet here’s the weird thing: If you pump Shortz’s name into Amazon these days, you won’t find his many crossword books at the top of the list. You’ll find something else—his books of Sudoku, the arriviste number puzzle that became a smash hit last year. Sudoku is the complete antithesis of the crossword: You fill in a nine-by-nine grid with the numbers one through nine so that no digit repeats in any column or row—nor can there be any repeats in any of the nine three-by-three boxes that make up the whole grid. It may sound complicated, but you can play it even if you’re completely illiterate—hell, even if you’re innumerate, since Sudoku doesn’t even require math. It is the ultimate puzzle for a postliterate world.

And it is making Will Shortz a mountain of cash. St. Martin’s, his longtime crossword publisher, began issuing his Sudoku books last year; it is now a 50-book series that has sold a mind-bending 5 million copies. Across the board, Sudoku has sold so prodigiously that it has pushed nearly every crossword book off the best-seller charts of Nielsen’s BookScan. At the end of May 2005, before the Sudoku storm arrived, a crossword volume was No. 1 on the charts for adult “games” books, and six of the other 49 titles were crosswords. One year later, Sudoku had wiped the slate clean: Forty of the top 50—including the top spot—were Sudoku books, and more than a third of those were Shortz’s.

All of which raises an interesting question: Has Will Shortz’s moment in the sun arrived—just as the crossword is being eclipsed?

Shortz is a slender, mustachioed man with a perennially impish grin—almost precisely what you’d expect a philosopher of puzzles to look like. “Puzzle people like to put things in order and to complete things,” he tells me. “Of the natural problems we face every day, very few have concrete solutions. We just jump in the middle and muddle through. But with a puzzle, you have that feeling of completion, which is very satisfying. You have not a solution but the perfect solution.”

Shortz loves things that work cleverly. He has decorated his Jazz Age mansion in Pleasantville, New York—headquarters for his puzzle empire—with antique furniture that was designed in reaction to the industrial age. “It’s all handmade, without using any nails,” he points out as he takes me on a tour.

Crosswords hold much the same appeal for him. They too are handmade: “Constructors,” word aficionados from all walks of life, craft the puzzles in their spare time and mail them to Shortz, praying he’ll publish them. He receives about 75 submissions a week but has exacting standards: A puzzle must be “jam-packed”— his favorite phrase—with unusual, new, or unexpected words. Though everyone assumes the killer Saturday and extra-large Sunday puzzles are the hardest to make (since the Times puzzles escalate in difficulty during the week), Shortz argues that Monday is difficult, too, because finding a fresh combination of well-known words is fiendishly hard as well.

Sitting at his computer, Shortz pulls up one of his favorite puzzles, by Brendan Quigley, a 32-year-old rock musician in Boston whose work Shortz frequently publishes. Quigley is famous for being the first constructor in the nation to use a new piece of slang or a brand name. This puzzle uses QUIZNOS—the submarine-sandwich chain—in the most challenging position possible, the bottom right-hand corner. NASDAQ and PEZ connect with the tricky final Q and Z. “Brendan’s grids are just packed with fresh uses,” Shortz says.