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Want to Know What the Future Holds? Look No Further Than the Nearest Crossword Puzzle

From Crosswords with Friends to the doozies in the “New York Times,” crossword puzzles are made by a band of freelance cruciverbalists whose constructions are founded on a deep-seated passion for the words we use—and strong opinions on the ones that are taboo.


The grid, full of restrictions and possibilities, has entranced graphic designers for hundreds of years. This story isn’t about them.There’s another kind of grid whose black-and-white beauty has bewitched a different group of equally meticulous problem solvers: the crossword puzzle.

It first ensnared David Steinberg when he was 12. He holed up in his bedroom to create a set of clues inspired by a board game (Clue, natch) and sent it off to the New York Times crossword editor, Will Shortz. The answer? “‘No’, as it deserved to be,” Steinberg recalls. But the rejection came with an encouraging note. Precociousness turned into perseverance, and Steinberg waded back into wordplay. “After my 17th submission, it was a ‘maybe,’” he says. “Finally, a different answer!” Eventually, the 14-year-old Steinberg became one of the youngest constructors to publish in the Times.

Unlike many other freelance creative gigs, the hallmark of the crosswords world is moments of encouragement, like a lukewarm note from a Times editor. Instead of vying for a tiny number of publishing slots while editors keep the doors locked and their emails unlisted, crossword puzzlers thrive on mentorship and collaboration.

Each week, 70-100 puzzle submissions are driven from the Times’ Manhattan office 30 miles north to Shortz’s Pleasantville home. For one summer, the door might have been answered by David Steinberg himself, grown from child prodigy to 19-year-old college sophomore, and living on Shortz’s couch during his Times internship. Every morning, Steinberg would pour out a bowl of Alpha-Bits (yes, you read that right) for breakfast and dig in to the submissions. As Shortz’s gatekeeper, Steinberg coded grids with check marks for “good” or “TDEME” for “Theme Doesn’t Excite Me Enough.” Exclamation points were best of all: language that was fresh and lively—the X-factor. Sometimes literally. One of Steinberg’s favorite puzzles used a Battleship game theme to scatter the grid with Xs, indicating how many hits it took to sink answers like DESTROYER or SUBMARINE.

Now 22, Steinberg has published 74 puzzles in the Times with answers like SASHAFIERCE and RAPBATTLE and swapped his major so he could edit for a local newspaper. His goal is to be one of the few cruciverbalists who work full time in the business, just like Shortz. At the Times’ rate of $300 for weekday puzzles and $1,000 for the weekend grids, most constructors are in the business for the laurels, not the paycheck. Jeff Chen, who’s published 78 Times puzzles and oversees a stats database called XWord Info, estimates that fewer than 10 constructors are full time. Instead of money, everyone chases that career-defining puzzle—their own “Battleship” grid, a one-song-glory puzzle that people will talk about for years to come.

Back in the day, crosswords were a hand-gridded, dictionary-fueled endeavor. Now, computer programs with built-in dictionaries are an industry norm. Constructors add lists of new words to their personal dictionary so the program’s algorithm can suggest it for a future puzzle. It’s a generous gesture for an expert to share their dictionary so a newbie doesn’t have to start at square one. As more software programs find a space in the industry, some publications are using the programs and the algorithm to auto-construct puzzle grids. Daily newspaper puzzles, though, are still bastions of the human hand.

XWord Info tracks a gold standard metric for constructors—the number of words they’ve debuted in the Times crossword. Elizabeth Gorski learned puzzling and code-cracking from her military cryptologist father. In the eight-person contingent of constructors who have pushed over 1,000 new words into the Times’ lexicon, Gorski ranks #3 with 1,514—from CLASSACT to MOTHERSOFINVENTION. “I want to incorporate new words to entertain solvers the way a chef adds new dishes to a menu,” Gorski explains.

Answers can be a barometer of the times. According to Chen, AMA used to point to the American Medical Association. Now, AMA points to the Reddit interview. Major themes can be subsumed from the data about the words our society is comfortable with, the ones we find unspeakable, and the inflection moments when that shifts. For example, for decades of the New York Times crossword, CHASTE was as much the watchword as it was at a local bible camp. THEPILL was called into action in 2013 and then used again with a doozy of a clue by XWord’s Chen: “Medical product with no conceivable use?” A sophomore at Brown University successfully inserted NUVA, for the birth control brand, into the lexicon in 2010. And, in October 2017, CONDOM burst onto the scene.

Clues are a reflection of societal norms and where they’re heading. “The industry is sometimes locked in the Mad Men era,” Gorski says. In a recent puzzle, Gorski clued AMAL as “Barrister/Activist Clooney” and was disappointed to see the editor update the clue to “Mrs. George Clooney.”

“I want to eliminate outdated, gendered ways of describing women and men,” she says. Gorski uses clues to literally redefine our cultural norms. NUN is a particular favorite. “I use “Convent manager” instead of the tired “Creature of habit,’” she says, noting that nuns have graduate degrees, and run schools and nursing homes. It’s hard not to picture Audrey Hepburn in a Givenchy lace mask in How to Steal a Million when Gorski confides that she and a band of likeminded constructors “meet in secret locations around the city… to avoid arrest.”

Once a year in late winter, a cadre comes together at the American Crossword Puzzle Tournament, run by Shortz at the Marriott Hotel in Stamford, Connecticut. Junkies for speed-solving puzzles pack the ballroom and shoulder into invite-only Jeopardy in the guest rooms. “Everyone makes puzzles and loves puzzles. You think: I have found my tribe,” says Brad Wilber, a reference librarian by day who’s also the crossword puzzle editor at the Chronicle of Higher Education. And attendees only want that tribe to grow. Perhaps as a part of the effort to mentor new voices, there’s a growing trend in collaborative constructing where an expert will pair off with a newer constructor. Working in teams comes naturally to many. “Be a partner and a critic at the same time,” advises Wilber. “Say, ‘I want as much of your work to survive the process as it can.’” 

Every constructor has their own puzzle point they want to get across, but at the end of the day, they’re working with one person in mind: the solver. “It’s the constructor’s job to set up the solver to ultimately triumph over the constructor,” says Chen. “You don’t want to create something that’s going to leave the solver defeated… It’s your fault if they don’t finish it correctly, not theirs.”

Emily Ludolph

Emily Ludolph writes about business, history, and culture. She has published in Quartz, Narratively, TED Online and Design Observer. She is the host of a live show and podcast called Dedicate It


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