On Aug. 23, 2022, Trey Mendez had his first crossword puzzle published in The New York Times. Like many creative types, crossword constructors — cruciverbalists, if you’re feeling dapper and Latinate — tend toward the autobiographical, and the theme of Mendez’s puzzle was no exception.

As a self-described “New Yorker with a mailing address in California who currently lives in Zagreb, Croatia,” his puzzle’s long, marquee answers were phrases about air travel whose first and last two letters were state abbreviations, as though the answers were linking those two states in flight. FLYING TIME, which starts with Florida and ends with Maine, thus was clued as “Duration of air travel from Miami to Bangor?”; VAPOR TRAIL as “What follows a plane going from Richmond to Chicago?”; and so on, out toward the horizon.

This crossword theme was appropriate not just for Mendez’s jet-setting modus vivendi but as a stand-in for the puzzle’s trajectory from inkling to ink. Mendez was the first mentee to be published from the Times’ Diverse Crossword Constructor Fellowship, a program launched in early 2022 with the aim, as the Times’ announcement put it, of “creat[ing] grids that reflect a range of cultural reference points.”

Everdeen Mason, the inaugural editorial director for games at the Times and the brains and bureaucratic brawn behind the fellowship, laid out the cohort’s first-class itinerary for me: Mendez and the other four fellows were matched with Times games editors for one-on-one mentorship, attended Times-produced seminars on subjects like crossword theme development and clue writing, and were ushered into a Slack workspace where they could pepper the editorial team with cruciverbal questions. All five fellows emerged from the three-month process with publication-worthy puzzles on file, and the Times will release one a month until they run out, then, per Mason, do it all over again. In his notes on the Times’ Wordplay blog, Mendez thanked the mentor he happened to be paired with, puzzlemaster and longtime crossword editor Will Shortz.

Target Audience

The Times’ program is one recent attempt to support word lovers on every leg of their journey toward becoming published crossword constructors. As a crossword constructor myself, I can attest it’s often a turbulent ride, from noting a quirk of language — that the word CONTINENTAL, say, is bookended by the abbreviations for Colorado and Alabama — to brainstorming a set of similar examples to building a fillable and varied grid to writing clever and relevant clues pitched to the right difficulty.

And beyond just the daunting task of assembling a salable puzzle, there’s the slings and arrows of cultural discouragement: crosswords that feel at best like they were written for an older, whiter audience and at worst let in insensitive language like slurs or off-key, even inaccurate clues. Propping up those puzzles is a loud minority of solvers that take to online comments sections to whinge about pop culture, tut-tut at the idea that the language in puzzles could carry political baggage and wax nostalgic for when the puzzle felt more like a buttoned-up vocabulary test than a bedazzled time capsule of current usage and slang.

Then there’s pricey, graphically outdated construction software and buyable “wordlists” that boast a ranked set of words to give a grid maximum pizzazz, neither of which are necessarily intuitive for the crossword neophyte.

Power of Collaboration

Happily, alongside efforts like the Times’ fellowship, a supportive and innovative “crossworld” has flowered. Open-source and user-friendlier alternatives to the pay-to-play tools of the trade are starting to circulate, including a project by computational chemist Brooke Husic and data scientist Enrique Henestroza Anguiano called Spread the Word(List), an idea spurred by Husic noticing “free access to a relatively clean wordlist was a major bottleneck for her mentees.”

Erica Hsiung Wojcik, a professor of psychology at Skidmore College, developed the free Expanded Crossword Name Database, tired of the fact that, as she put it, many crosswords “tend to reference a narrow band of cultural knowledge and experiences that speak to a certain type of solver who knows a lot about the history of baseball and Italian food and nothing about popular music from the 2000s or Sichuan cuisine.” If a crossword, by its nature, is going to feature vowel-heavy, stalwart three-letter answers, reasoned Wojcik, why not make those recurring characters novelist YAA Gyasi, for example, rather than Mel OTT or Bobby ORR?

And while the archetypal solving or constructing session might seem like a lonely pursuit, this new generation of puzzle lovers prizes collaboration. On a Discord server dedicated to crosswords, newbies and veterans alike bat theme ideas back and forth and, like a present-day haiku contest, write comments that have either 15 or 21 letters (the standard crossword is 15x15 squares; bigger puzzles like the Times’ Sunday crossword are frequently 21x21). To the new guard, culture is nothing to shy away from, unless it risks alienating solvers: They’ll hunt down the real-life versions of crosswords that appear in film and TV (recently getting to the bottom of what puzzle Tony was solving in an early episode of The Sopranos, a collective effort that even involved phoning an archivist in Newark); they’ll debate whether references to Harry Potter need to disappear given J.K. Rowling’s history of transphobia; they’ll also, in a bid to inject new life into another grid mainstay, add to a crowdsourced spreadsheet listing over 200 clues for the word OREO. Why settle for “Dunkable cookie” when you could go with “Cookie split by Ross and Rachel in the first Friends episode?”

Over at Twitch, the video game live-streaming giant, new solvers and tournament-winning speed demons stream themselves polishing off a crossword — some of whom challenge themselves by looking only at the Down clues, ignoring the Acrosses — as digital cheerleaders shout punny encouragement (and occasionally a spoiler, though that’s verboten) in the chat. And a Facebook group called the Crossword Puzzle Collaboration Dictionary, created at the suggestion of Times blogger Deb Amlen and run by two young full-time puzzlers, Erik Agard and Will Nediger, matches would-be constructors from underrepresented groups with mentors. 

Providing a Platform

Accompanying these construction aids and digital agorae or public spaces is a proliferation of alternative and indie crossword venues. There’s The Inkubator, a subscription service that lists among its goals “provid[ing] a venue for women to exhibit and get paid for high-quality puzzles, especially (but not exclusively) puzzles that may not have a chance at mainstream publications due to feminist, political or provocative content.” There’s Queer Qrosswords, the project of constructors “fed up with the heavily cis/straight nature of most mainstream crosswords” and who, in lieu of payment, ask subscribers to make a $10+ donation to an LGBTQ+ charity of their choice; to date, its two puzzle packs have raised over $60,000 for LGBTQ+ organizations. And there’s the revived USA Today puzzle, helmed by Agard, widely recognized as one of the main forces behind these recent strides toward inclusivity.

Agard has a knack for reimagining stale crossword fill for the modern day. In his hands, the common crossword answer ONT — normally clued as the abbreviation for Ontario — is recast as ON T, as in taking testosterone, and so becomes one of the few crossword entries geared toward the trans community. Kameron Austin Collins, a film critic and constructor for The New Yorker, similarly pointed to TOP SURGERY as a quintessential Agard answer: “politically persuasive,” “inferable” (because solvers who don’t know the phrase should be able to piece it together from its constituent parts) and “powerful” (because solvers who do know the answer might finally feel like the crossword was made for them too).

On the very same day as Trey Mendez’s Times debut, Agard’s crossword in The New Yorker featured DIGITAL BLACKFACE (“Modern-day form of minstrelsy”) stacked on top of ANISHINAABEMOWIN (“Language in which ‘boozhoo’ is a greeting”). If the first is a neologic concept or newly coined phrase prominent in modern discourse on online ethics, the second, another word for the Ojibwe language, ought to be much more prominent in contemporary life, including crosswords.

Part of the bid of the inclusive crossword grid is a hope the solver will develop the same broad-based curiosity after solving that the constructor had before the puzzle was in the world, as they were building the grid and writing the clues. Part of the crossword’s power is lucky juxtaposition, seeding connections and semantic rhymes that feel unbidden yet natural when words are placed side-by-side in the black-and-white grid.

As a constructor, it’s those moments of serendipity that give the crossword an almost spiritual linguistic aura. Researching clues is a lot like researching an article, and while sifting across dozens of browser tabs and searches, I googled Trey Mendez, only to find the debut crossword constructor shares his name with the current mayor of Brownsville, Texas. I’d recognized the name, I realized, because he’d been in the news for coming out against Title 42 (immigration expulsion rule) and for glad-handing with billionaire Elon Musk, who located a SpaceX facility in nearby Boca Chica. On the one hand, a creator of a language game and a newsworthy mayor were linked through a trick of homography; on the other, the doubling was a reminder that crosswords have their politics too, however seemingly miniature. There’s work left to be done, but the new guard of crossworders is off to a flying start.

This post was adapted from an article written by Natan Last with illustrations by Aysha Tengiz, in the Winter-Spring 2023 issue of The Henry Ford Magazine.