‘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 – or “cruciverbalists”, in the parlance – 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 fulfilment, 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.”

Londoners will love Aisling Bea’s This Way Up. We might roll our eyes a little

---

Ryan Tubridy: With sturdy self-belief, our best-paid broadcaster hits his summer groove

---

The Movie Quiz: Anthony Hopkins has played Hannibal how many times?

---

A one-day music festival in Meath to renew the soul: Next week’s live and online events

---

Shortz’s stature in the crossword world is difficult to overstate. Observers, like the Kremlinologists of yore, speak of the “Shortzian” and “pre-Shortzian” eras. Even his critics, particularly younger and female crossworders, who believe the Times puzzle is too white and male, acknowledge his “visionary leadership”.

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.

In a 2006 documentary, Wordplay, the comedian Jon Stewart says: "When you imagine Crossword Guy" – Shortz – "you imagine he's 13 to 14in tall, doesn't care to go more than 5ft without his inhaler. And yet he's a giant man. He's the Errol Flynn of crossword-puzzling. Meeting him in person, I definitely thought, 'Well, I was planning on taking your lunch money, but now I believe you could best me, in a physical joust, if you will.' So I backed off immediately."

Meeting Shortz on a recent Friday, I discover that Stewart has exaggerated, but only slightly: Shortz, 68, is of medium height and build, although, like Flynn, he has a moustache. And later, when I face him in table tennis, I feel like a mouse who has suddenly found himself getting a free ride in the talons of a hawk.

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 artefacts 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.

Letters

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.

Shortz has guest-starred in numerous television shows and movies, including The Simpsons. The creators of Batman Forever asked him to write riddles for the Riddler

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 weaponised, 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."

Changing language

Shortz is something of a man about town. He has guest-starred in numerous television shows and movies, including an episode of The Simpsons. The creators of the 1995 film Batman Forever asked him to write riddles for the Riddler.

Then, in 2004, the Japanese logic game sudoku arrived in Britain. It was a juggernaut. Soon every British newspaper was printing sudokus along with crosswords. US publishers braced for impact. Shortz's book editor called, and said: "I need three volumes of sudoku, and I need them in two weeks." He enlisted a friend in the Netherlands who wrote computer programmes. Using a math algorithm, they met the deadline.

The first volume sold 1.2 million copies. “It was a lot of money.” He laughs. “The books are still selling, though the craze has died down.”

“[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 clear-cut 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 Defence Initiative) no longer elicits the recognition it did during the Reagan administration. Similarly, the ice bucket challenge – as a clue for ALS, the illness that the activity raised money to fight – feels like ancient history. Shortz doesn’t like clues about illness, anyway: “Crosswords are supposed to entertain people and lift them up. It’s no fun to think about disease.” That clue became “Vice-President Gore, and others”: Als.

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. But the misstep seemed to validate a common charge: that the cultural blindspots of crossword editors, who are mostly white and male, are reflected in the crosswords that they choose and the clues that they accept or reject.

Shortz offers to take me to see his table-tennis club. As we walk to the door, he accidentally kicks over a pile of priceless rare books, but he seems untroubled

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

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, or be forced aside by the Times. Of the four people who have held his position, he has already had the longest tenure.

“I have outlasted them all,” he says.

“Would your departure incite a power struggle?” I ask.

Shortz looks tickled at the possibility. But he gives a diplomatic answer praising his colleague Joel Fagliano.

One rising star of the crossword world is Erik Agard, a former champion who became USA Today'scrossword 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 revolutionise 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.

Table tennis

After we’ve talked for a while, Shortz offers to take me to see his table-tennis club. As we walk to the door, he accidentally kicks over a pile of priceless rare books, but he seems untroubled.

We hop in his car – a recently acquired sporty white Alfa Romeo – and drive to the club, which is only a few minutes away. He has neglected his seatbelt, causing the car to emit an insistent pinging noise, so I briefly steer while he puts it on.

Shortz opened the Westchester Table Tennis Center in 2011. He plays for an hour or more every evening. He hasn’t missed a day, he says, in eight and a half years. (He remembers the exact day.)

Shortz attempts to teach me table tennis – no sportsman calls it ping-pong, a term associated, scornfully, with 'garage players'

“You get some of the same satisfaction from a tough table-tennis game as you get from solving a tough puzzle,” he says. “You block out everything else in the world.”

I had pictured a dusty church basement with a few rickety playing tables jostling for space with broken pews; instead we're greeted by a modern, bright gymnasium with dozens of tables. About 15 people of diverse ages and ethnicities, almost all men, are milling around. The club has three full-time pros, including the former national table tennis coach of Barbados, a former member of the Ghanaian national team and the six-time champion of Togo.

Shortz attempts to teach me table tennis – no sportsman calls it ping-pong, a term associated, scornfully, with “garage players” – but after I sufficiently embarrass myself I bow out. He starts playing with a young man close to a third his age.

The game quickly escalates in intensity and violence. The ball ricochets between them at unsettling speed, cutting ever-wider arcs through the air. To the small plastic ball hurtling across the table, the other side of the court must appear something like an aircraft carrier to an approaching fighter jet: a distant speck of landing strip, dauntingly tiny and far away, yet looming closer at terrifying speed.

Shortz’s earlier manner – amiable, unhurried, slightly dishevelled – has been replaced by intense and total focus. When a point is scored, or a ball goes off-side, he resumes playing immediately, with no pause for breath, and with redoubled fervour.

He only reluctantly calls the game short when he remembers that he has offered to drop me at the train station. My train leaves in 12 minutes.

As we walk out, I ask, “Who was winning?”

“Oh,” Shortz says, “that was just –” He gestures vaguely. “We weren’t keeping score.”

Then a sly, Cheshire smile spreads under his moustache. "But I was."– Guardian