“The Life of the World’s Most Powerful Crossword Editor”

From a story on theguardian.com by Oliver Conroy headlined “‘I’ve outlasted them  all’: the spectacular life of the world’s most powerful crossword editor”:

Every day thousands of people vie to outsmart one man: Will Shortz, the New York Times’s crossword editor of almost three decades.

Crossword fanatics…must get their fix, and they prefer to get it from a man whose puzzle is considered the gold standard. Depending on a puzzler’s skill and temperament, and on the day of the week (Monday puzzles are easiest, Saturdays hardest), that puzzler may race to the finish, surging with triumphant dopamine, or shatter a coffee mug against a wall.

“I think humans have a natural desire to fill empty spaces,” Shortz tells me, as we sit in his Tudor-style house north of New York City. “It gives us a sense of fulfillment, to complete a grid.”

He adds: “When we start filling in the last squares, it brings a rush of adrenaline and dopamine. It’s a great feeling, like a little drug.”…

If it’s lonely at the top, Shortz doesn’t look it. He’s as busy and energetic as ever. In addition to editing the Times crossword, he does a weekly radio crossword on NPR, directs the American Crossword Puzzle Tournament and founded and owns the United States’s largest table tennis club….

Shortz’s aura is meticulous yet occasionally chaotic; it is embodied in his charming, slightly cluttered house, which doubles as the home of what could be called the Shortz Collection: more than 25,000 puzzle books and magazines, including one from 1533, and various puzzle-related artifacts and trophies. The shelves of his library, long full, are supplemented by towers of paper two and three stacks deep. Forced to retreat from the library, Shortz uses a small adjacent room as his office.

While Shortz shows me the first copy of the first edition of the first-ever published crossword book, his intern, Owen, a student at Princeton, shuffles around in the background. Although countless people do crosswords, far fewer construct them. Ambitious journeymen seek apprenticeships with master puzzlers.

At the Times and other publications, contributors submit crosswords, and are paid if theirs are chosen. (The Times offers the industry’s highest rates – up to $750 for a weekday puzzle, and up to $2,250 for a Sunday – and authors are credited.) Every day Shortz and his colleagues choose submissions, factcheck and tweak them, then send them to test solvers. After editing, about half the clues in a typical puzzle are the author’s and half are Shortz’s.

Shortz, who was born in Indiana in 1952 and raised on a horse farm, has made puzzles since he was eight or nine. His interest in wordplay and competition was influenced by his mother, a writer of children’s stories and articles with a knack for winning corporate writing prizes. By writing limericks, short stories and, on one occasion, the name for a new line of chewing gum, she won their family money, appliances and two cars.

At 14, Shortz sold his first puzzle. At 16, he began contributing to puzzle magazines. In college, where he did a self-designed major, he earned the world’s first degree in enigmatology, the study of puzzles. He also did a law degree, but never took the bar, because he went immediately into a career in puzzles.

In 1993, after a successful run as the editor of Games magazine, Shortz became the Times’s crossword editor. Today, the section has a staff of five; when Shortz started, it was just him. “The first couple of months were bumpy,” he says.

He quickly learned that you can’t please everyone. He got 25 to 50 letters a week, mostly from the displeased. In the documentary Wordplay, Shortz reads some hostile correspondence: “This is both idiotic and completely unfair …” “You should be hanged by your cojones …” “Frogs hop, sir, but toads do not. They waddle.”

Today he gets less hate mail. People vent on online forums or post puzzle reviews on blogs. Crossword bloggers, whose considerable vocabularies are easily weaponized, can be “unsparing”, in the words of the crossword constructor Anna Shechtman, a former assistant to Shortz whose high-meets-low crosswords for the New Yorker embrace pop culture and feminist intellectuals. The more common approach, however, seems to be damnation by faint praise. “I got absolutely zapped by a couple of proper nouns I’d never heard of,” one recent review says, “but otherwise, it was all perfectly fine. Highly competent. A very plain and inoffensive Sunday.”…

“[People] like to be challenged,” Shortz says. “Think of it this way: we’re faced with challenges every day in life. Most of them don’t have clearcut solutions. Human-made puzzles have perfect solutions.”

A crossword editor is a cultural arbiter. When words and phrases lose currency, an editor may make the painful decision to put them to pasture. For example: SDI (Strategic Defense Initiative) no longer elicits the recognition it did during the Reagan administration.

Language is also political. In 2018, Shortz ran a puzzle containing a word, beaner, which is sometimes a slur against Mexican Americans. (The clue was: “Pitch to the head, informally.”) He apologized, saying that he was unaware of the word’s connotations, and also noting that he considers the specific usage of a word when evaluating offensiveness….

Shortz says. “Traditionally crossword constructing has skewed white and male – not just at the Times, but everywhere.” Thirty percent of the crosswords the Times published last year were by women, he says, but only 20% of submissions were from female constructors. He adds that the crossword section’s staff is half female and includes people of color.

Shortz, who recently passed the milestone of having edited more than 10,000 Times crosswords, says he has no intention of retiring – ever. For a new editor to take power will require that Shortz either die (at the hands of a rival, one imagines, or an irate crossword fan), or be forced aside by the Times. Of the four people who have held his position, he has already had the longest tenure….

One rising star of the crossword world is Erik Agard, a former champion who became USA Today’s crossword editor after the previous editor was accused of plagiarism. Agard is regarded as something like the Picasso of crosswords. Like Schechtman, Agard has made no secret of his desire to revolutionize them with more “inclusive” and cutting-edge clues – meaning ones less tailored to a reader whose presumed cultural knowledge is middle-aged, straight and white….

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