BEHIND THE SCENES

The Crossword King

Tap to read how Will Shortz makes the New York Times puzzle.

New York Times Crossword

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“Albertan,” says Will Shortz, crossword editor at The New York Times.

Long pause.

“Could do ‘Resident of Edmonton.’”

Long pause.

“It’s a little easy, though,” says Joel Fagliano, the Times’ digital puzzle editor: “I was thinking ‘Neighbor of a Montanan.’ Nobody ever goes across the border for this kind of clue. Is that fair?”

“For Thursday it is,” says Shortz.

The two men are working from a small office in Shortz’s Tudor-style home, in a leafy suburb 25 miles north of Manhattan. Shortz is in a swivel chair, Fagliano at a computer. They spend three to four days a week editing together and are currently in the middle of a Thursday crossword (Times puzzles get tougher as the week goes on). This one will appear in a few weeks, reaching 400,000 crossword subscribers.

Shortz (left) has edited NYT crosswords for the past quarter-century.

With such a prominent audience and more than 75 years of crossword history, the New York Times Crossword app has fundamentally changed how solvers engage with their daily puzzle. And yet the process of making it is thoroughly timeless.

“How has the app changed my job? Not at all. A good crossword is a good crossword,” Shortz says. “But from the solver’s standpoint, things have changed a lot.”

The fastest time for a Monday puzzle (the easiest) in the newspaper is about a minute and a half. In the app? A minute and twelve seconds. That’s because it’s faster to type than write. And there’s no hunting for the clues.

The app highlights the specific clue when you select the answer you want to focus on. It keeps track of your time. It tells you when you’ve successfully completed, say, 47 crosswords in a row. And it gives you access to all 13,000 puzzles Shortz has edited since 1993, when he was hired by the Times.

Solving in the app is typically faster than solving on paper.

Start from the beginning and work your way forward. Or select one of the dozens of “puzzle packs” curated by Fagliano and organized by often novel themes: Americana, Back to School, Turkey Trot, Wordplay. Or you can play the hugely popular 5-by-5-grid Daily Mini puzzle written by Fagliano.

And for when you get stuck, there are “hint” and “reveal” functions. “It’s basically cheating,” says Shortz. “But it doesn’t matter, because it’s your puzzle.”

Memorable puzzle-making is as much about cleverness as it is about accuracy.

The editing process is not stuffy. Shortz often reads a clue, submitted by a writer, and then engages in what can best be described as thinking out loud.

Certain clues reveal a generational difference between Shortz and Fagliano that helps keep clues fresh, but not so fresh they’ll seem archaic in a year.

Shortz: “Elsie. ‘Famous cow.’”

Fagliano: “There’s a character on Westworld named Elsie.”

Shortz: “Is she significant? What can we say about her? ‘Westworld woman’? That’s pretty vague. How about ‘Woman’s name that sounds like two letters of the alphabet’?”

Fagliano: “Let’s do that.”

Shortz gets all wrapped up in words.

Even if the app hasn’t changed the puzzlemaker’s job, the digital age has affected it profoundly. “I have a fantastic reference library,” Shortz says. “But now you can check virtually anything online, and we do.” Anyway, memorable puzzle making is as much about cleverness as it is about accuracy.

Shortz: “Styx. ‘Mythical river.’ That clue is fine, but it’s not fun.”

Reporter who can’t help himself: “What about the band?”

Shortz: “Is Styx around anymore? Obviously they’re not having hits. But are they still touring? Could say they were big in the ’70s and ’80s.”

Fagliano: “‘Come Sail Away’ band? ‘Mr. Roboto’ band? They had the song ‘Lady.’ I don’t recognize this number-one hit they had. ‘Babe’?”

Shortz: “You know ‘Babe’!”

Fagliano pulls up “Babe” on YouTube. The pair listens in silence way past the point it becomes awkward.

Shortz: Let’s go with ‘Band with Top 10 hits “Lady” and “Babe.”’ First of all, they’re both short. And second, they’re both people.”

Someone once said that if you ever get tired of writing, then you’re tired of life. I feel the same way about puzzles.

—Will Shortz

Crosswords the old-fashioned way.

It’s this kind of playfulness that keeps Shortz making puzzles, even after editing 13,000 crosswords, hosting 20 annual tournaments, and developing the Times app.

“I’m as excited about them as I ever have been,” he says. “I’ll never get tired of them. Someone once said that if you ever get tired of writing, then you’re tired of life. I feel the same way about puzzles.”

Shortz moves his attention back to his work. “Look at this clue we were editing earlier. Yacht. ‘Pleasure boat’ seemed too easy for a Thursday. So Joel suggested ‘Vessel with 1 percent occupancy.’”

Shortz taps his pencil on a clipboard. “Ha!”

    New York Times Crossword

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