On Sunday, June 9, The New York Times published its 25,415th daily crossword since the newspaper debuted its first in 1942. Times puzzle editor Will Shortz mentioned that this particular crossword had been in the works for more than a decade—but as the puzzle-obsessed internet immediately pointed out, it could have been much longer. The clues included a Waltons actor who had been dead for 40 years; inelegant acronyms or abbreviations showed up as answers 11 times, including the nearly unforgivable double abbreviation MTST (the clue: “____ Helens”). “Cringeworthy,” one person wrote on Twitter. “This puzzle feels like it was sitting in a box … for decades,” wrote another.
Other offenses in the puzzle riled for different reasons, which Rebecca Falcon, a 30-year-old crossword constructor, enumerated at length on Twitter. It used PATERNO without acknowledging that the football coach has been criticized for his response to Penn State’s child-abuse scandal, and answers mentioned only four women, two fictional and two dead. One of the names, ROXANE, could have been clued as a reference to best-selling (and living) author Roxane Gay but instead defaulted to a character from the 19th-century play Cyrano de Bergerac. Another puzzle-maker, who writes The Washington Post‘s Sunday crosswords, showed how easy it would have been to replace PATERNO with the phrase AM RADIO. “The message here and all too often from the Times,” Falcon wrote, “is that to be relevant enough for mainstream crossword inclusion is to be male.”
The crossworld—a loose collection of people who analyze puzzles the way others do hip hop lyrics or fantasy novels—kibitzes about every major puzzle published in newspapers and digital subscription services, but most of its critiques aim squarely at The New York Times. It’s obvious why. Even if you’ve never solved a crossword, you know the Times‘ reputation as the gold standard of cruciverbalism. It has the biggest audience and casts the longest shadow. More than 500,000 customers pay up to $40 a year for stand-alone crossword subscriptions, and millions solve the crossword each month on the Times website. It’s where every crossword constructor wants to be published. But because the culture is changing, puzzles are changing too—and though those changes didn’t start at the Times, constructors are going to make sure they take root there.
The New York Times was decades late to the crossword craze. Puzzlemania had struck in the 1920s, inspiring songs like “Cross-Word Mamma, You Puzzle Me (But Papa’s Gonna Figure You Out),” but the Gray Lady’s concession to popularity vaulted the pastime into higher-browed territory. Margaret Farrar, the puzzle’s inaugural editor, imposed Times-ian rigor on what was then considered a thoughtless amusement, codifying most of the rules you know today: The grids are nearly always square; words must be three letters or longer; black squares must be arranged symmetrically so that the grid’s pattern looks the same upside down; every letter should be “checked,” meaning it appears in both a word reading across and one reading down, giving you two chances to figure it out.
Since Farrar’s retirement in 1969, only three other editors have overseen the institution, each infusing the crossword with their own distinct philosophy. Never was that more starkly felt than when Shortz joined the paper in 1993. As a student at Indiana University, Shortz turned his love of puzzles into a self-created college major in “enigmatology.” When he came to the Times after a stint at Games magazine, he was determined to spread that love. “What I tried to do is modernize the puzzle to the language,” he says. “To have the puzzle reflect life.”
The previous editor, Eugene Maleska, famously hated contemporary pop culture, and puzzles under his watch habitually relied on obscure terms from zoology and botany. (UNAU—a sloth—was a favorite.) Shortz did away with such crosswordese and began publishing colloquial phrasings, brand names, and movie references. “The crossword is in a newspaper,” he says. “A smart, cultured, well-read person should be aware of everything.” Within a month, INDIGO GIRLS, MUPPET, and BENCH PRESS made appearances. “I was 35 years younger than Eugene, so there was immediately a change in tone,” he says. “A lot of older solvers were upset.”
Maleska purists grumbled—the only thing that goes better with a crossword than morning coffee, after all, is a complaint—but the puzzle drew in new solvers and expanded its cultural cachet. A 2006 documentary, Wordplay, visits some of the Times crossword’s celebrity obsessives: Jon Stewart, Bill Clinton, and the same Indigo Girls whom Shortz had included in a puzzle his first month on the job.
More importantly, Wordplay showed legendary constructor Merl Reagle designing a puzzle on the fly. Seeing that dance of squares and science proved to be the moment of conception for a new generation of constructors. “I was 15 when it came out, and it was a paradigm-shifting film for me,” says Anna Shechtman, who spent a year after college as Shortz’s assistant and today writes puzzles for The New Yorker. “I’d never even thought about solving puzzles, but I wanted to start constructing after seeing it.”
Those inspired by Wordplay had the good fortune to embrace a calling that was more accessible than ever before. Shortz had arrived at the Times just as web browsers were bringing people online in great numbers. As it did with so many other interests, the internet provided a framework for crossword fandom, a tribal sprawl that transcended location and circumstance. But it also provided a framework for pedagogy: Veteran and aspiring constructors discussed their craft on forums and listservs, with the established mentoring those just starting out. Fueled by discourse and community, this trifle for passing the time on the train or in a waiting room began to take on a new urgency.
The Internet didn’t only allow for congregation, it also created new routes for publication. In the late ’90s, a crush of websites began running puzzles online: Billboard, the Discovery Channel, sports leagues like the PGA Tour and Major League Baseball, digital-only publications like Slate. By the mid-2000s, alternative weekly newspapers started publishing puzzles from young constructors. Drug and sex references might not have flown in the Times, but they were fair game for the San Francisco Bay Guardian or the Chicago Reader.
A twentysomething named Ben Tausig was behind many of these puzzles. By the time he’d turned 25, he was able to quit his job at a museum thanks to his successful syndicated puzzle, Inkwell.
He went on to edit the crossword for the A.V. Club, a sister publication of the satirical newspaper The Onion, and then, in 2012, after the A.V. Club dropped its puzzle, raised money to revive what was called the American Values Club Crossword, aka AVCX. Tausig, now 38, says that at AVCX they “started making a serious effort around inclusion.”
A long-percolating discussion in the construction community was beginning to boil over, emboldened by an assessment of some numbers at The New York Times. Under the first two editors to succeed Margaret Farrar, women wrote or cowrote more than a third of the paper’s crosswords. Under Shortz, that number has dwindled to 20 percent, according to XWord Info, a blog that tracks every crossword published under Shortz. Last year, women wrote or cowrote 16 percent of the Times‘ daily puzzles. A similar dearth of women exists at most other major publications with well-regarded puzzles: Los Angeles Times, The Wall Street Journal.
“It’s one of those times where it feels so right to call something structural or systemic,” says Shechtman. “It’s not that any individual editor or outlet is insidiously excluding people.” Still, it’s hard to ignore that, at each of those outlets, the editor is a man in his sixties or seventies. (At the Journal, puzzle editor Mike Shenk has frequently published his own puzzles under female pseudonyms; the paper announced in January that it would be ending that practice.)
Nor is gender the only point of criticism. On January 1 of this year, BEANER appeared in the New York Times puzzle. While the clue itself was innocuous—“Pitch to the head, informally”—many wondered how Shortz had green-lit a word known as a racist slur. Shortz issued an apology the same day, claiming neither he nor his assistant had ever heard the word used in such a way.
Tausig and his partners began seeking out constructors from communities that were underrepresented in the cruciverbalist ranks and offering to mentor them with an eye toward getting them into AVCX. About half of its puzzle-makers are now women, and some of its young constructors are popular at The New York Times. Deb Amlen, who wrote puzzles for feminist magazine Bust and was one of Tausig’s early recruits, today runs the Times‘ daily crossword column.
Another AVCX star, 25-year-old Erik Agard, is regarded as one of the most talented constructors of his generation. Tall and lanky, with his hair worn in an enormous Afro—his Twitter bio reads “gene maleska but statuesquer”—Agard wrote or cowrote 10 Times puzzles in the first half of 2019. Like Tausig, Agard has emerged as an advocate for other underrepresented constructors. “I wouldn’t be doing this without Erik,” says Laura Braunstein, a frequent AVCX contributor. “When I was starting he said, ‘Why don’t we collaborate on something?’ That was the first time my name was on a New York Times crossword.”
Last year, Braunstein and another constructor started the Inkubator, a subscription puzzle series that features only puzzle-makers who identify as women. Two other series—Queer Qrosswords and Women of Letters—also make representation their aim. For Queer Qrosswords founder Nate Cardin, a 36-year-old constructor in Los Angeles, the project was born of the desire to see yourself in the puzzles you solve. “I kept feeling like I was an intruder,” he says. “Even in major publications it would have clues like ‘Husband’s spouse’: WIFE. ‘Towels his and ____’: HERS. I always felt that I had to put part of myself aside and pretend that I was straight in order to solve these as efficiently as possible.”
Rebecca Falcon, who called out the Times’ use of PATERNO, has poured her own frustrations into puzzles she publishes online, including one called “#BelieveWomen” that included as theme entries seven men accused of sexual misconduct. (Turns out LOUIS CK and HARVEY WEINSTEIN make pretty great answers.) “It’s just a crossword puzzle,” says Falcon, “but at the same time it’s so much more than that—it’s a sign of resistance.”
Click here for a printable version. If you’d rather solve on a computer or an app like Across Lite or Standalone, download the .PUZ file here.
Answers to the puzzle can be found at: WIRED.com/puzzlesolution
People don’t make crosswords solely as a political act, of course. They do it because they love puzzles. And once you’ve become proficient as a solver, construction represents a puzzle all its own. If you’ve ever felt the mental Legos snap into place when you’ve thought your way through a particularly confounding clue, you can imagine the satisfaction that comes from arranging dozens or even hundreds of words into a tightly packed grid. That’s when engineering becomes art.
“Every puzzle should have the mark of its creator,” says K. Austin Collins, a mainstay of AVCX and The New York Times. “That’s what people say when they want diversity.” His Times debut was a 2014 puzzle that marked the first time ANITA HILL and JAVASCRIPT ever appeared in a grid, and his 11 puzzles since have at times felt like an ever-evolving record of pop culture: BOOTYLICIOUS. KOBE BRYANT. COMMITMENTPHOBE. REDDITOR. Collins’ word fill reflects the worldview of a film-obsessed, 31-year-old, gay, black constructor—but also the worldview of any plugged-in young person, period.
When I first pitched this story to my editors, they approved it on the condition that I actually make a puzzle to go with it. At WIRED, we refer to this kind of outcome as “getting green-lit off a cliff”—an especially fitting metaphor given the vulnerability of the project. I’m used to having my writing read by others, but crosswords have always been intensely personal for me, and turning that into a solvable work of its own somehow felt like boiling down my essence and pouring it into the 225 tiny squares in a 15-by-15 grid. Not to mention the whole can-I-actually-do-this part: While I’ve made dozens of half-starts at constructing crosswords, that also means that, well, I’ve made dozens of half-starts at constructing crosswords.
To make a puzzle for WIRED, though, I had some help. My previous attempts that ended with worn-down erasers and crumpled-up pieces of graph paper had relied on whatever vocabulary and recall I brought to them. In recent years, puzzle-construction software and word-lookup websites have turned writing crosswords from a purely organic intellectual exercise—you, your brain, and maybe some reference books—into something with a dash of the digital. Tools like Crossfire or Crossword Compiler are able to suggest entries that hew to the constraints of your grid; even better, since constructors can upload their own curated word lists to the software, those entries can be both contemporary and personal. As a result, these tools have become standard. “I’d say all the top constructors now use computer assistance,” Shortz says.
The first element to building a good crossword, as any constructor will tell you, is coming up with a unifying concept. This can be as jaw-droppingly intricate as designing a grid in which the pattern of black squares looks like the spiral shape of the Guggenheim Museum—as Elizabeth Gorski famously did to celebrate the building’s 50th anniversary for a 2009 Times Sunday puzzle—or it can be as simple as including a handful of entries that share the same wordplay twist.
I wanted a theme that felt at home in WIRED, so I brainstormed words and phrases that might lead to something. My first breakthrough was that SATOSHI NAKAMOTO, the pseudonym of the person who first conceptualized bitcoin in 2008, was 15 letters long—perfect to stretch across the crossword grid. Maybe there was a twisty connection to be made with the idea of “blockchain.” Maybe I could use a black square to interrupt, or block, well-known chains! BEST[square]BUY, maybe, or OLIVE[square]GARDEN. Maybe I could … realize that the idea was both contrived and made the grid feel like sponcon. After a quick break for unlimited sadness and breadsticks, I pressed on.
(ALERT: If you haven’t solved the puzzle in this story, now’s your chance—a major hint and spoilers follow.)
My next idea was to create a theme punning on famous tech CEOs’ names. I wrote down a tortured menu of CEO-inspired foods: EGGS BENIOFF, NADELLA SPREAD, PICHAI MELBA. Pun quality aside, my puzzle shared a problem with the tech industry: The only female CEO with immediate name recognition was YouTube’s Susan Wojcicki. WOJCICKI SOUR might have been a decent cocktail pun, but I didn’t want the answer for the only woman to sound even indirectly negative.
That tension ended one puzzle concept but led to another: I might be able to build a puzzle around the very concept of the gender disparity in executive boardrooms—which just happened to lend itself to a 15-letter phrase to stretch across the entirety of the grid. (That’s the big hint.) That I’d landed on the idea was no huge surprise; the effort to diversify the construction community had come up time and time again in interviews with constructors and editors.
Those conversations also made me keenly aware of the fill and clues I would put into the puzzle. The word GRACE could be anything from “a prayer before eating” to “Frankie’s partner on a Netflix comedy,” but it could also celebrate one of computer science’s most important researchers, Grace Hopper. I knew my own frame of reference would be in there—Pharcyde song titles, Star Wars—but by stretching a little bit I could add some valuable context.
The fewer black squares, the more “open” a grid is, and many constructors pride themselves on being able to stack groups of 11-, 12-, or even 15-letter entries atop one another. Not this rookie! My grid had a reasonable 76 entries, with only a couple of longer entries. This is where the beauty of software truly came in: I could prompt it to suggest candidates for those longer entries, or any other ones, simply by mousing over the entry in question.
It’s also where I found the software’s limitations. Crossfire’s word list, while large, is riddled with both Maleska-style obscurities and sizable holes. Entries like CAT TOY and HULU, let alone emergent terms like ENBY, were nowhere to be found. There was a joy at finding all those terms lurking in my brain—landing on CAT TOY when seeing C_T_OY—but there was also joy at thinking how gratifying it might be for a nonbinary solver to see ENBY in the puzzle. We all contain multitudes, and we all deserve to see as much of those multitudes as possible in things that give us pleasure.
The new generation of puzzle enthusiasts, like any indie scene, pale in number to The New York Times‘ or The Wall Street Journal‘s massive audiences. Ben Tausig puts the subscription numbers for American Values Club at “four or five thousand”; Inkubator hovers somewhere around a thousand. Yet they are a force. “In a way, they’re some of our fiercest competition,” Shortz says of these other outlets. “Not in the sense that they have hundreds of thousands of readers, but they compete in terms of quality and prestige.”
The fiercest competitor is one that Shortz didn’t name. The New Yorker, that august publication of arts and letters (which, like WIRED, is published by Condé Nast), began publishing a weekly puzzle in 2018. Its founding editors reached out to Anna Shechtman to help recruit a roster of constructors. “We wanted gender parity 50–50,” Shechtman says. “We also wanted constructors of color, queer constructors, and to make sure we had generational representation as well. We didn’t want just millennial constructors.”
Shechtman, who’s finishing her PhD in English literature and media studies at Yale, is one of a multicultural, accomplished septet of New Yorker constructors, which also includes Erik Agard and K. Austin Collins. For an example of what that can lead to, consider Agard’s puzzle that appeared on NewYorker.com on June 14. As you might expect from the publication, its 72 clues made references to novelists (Naguib Mahfouz and Celeste Ng), art (the location of the road depicted in the painting The Scream), and politics (US representative Ilhan Omar). The overwhelming impression the puzzle gave, however, was that this wasn’t your AP English teacher’s coffee-break diversion. Clues involved rappers 21 Savage and Megan Thee Stallion; WNBA superstar NNEKA OGWUMIKE showed up in the grid. It managed to be intellectual without being arcane, contemporary without being gimmicky. Of 19 proper names that appeared, 14 were women, most of them nonwhite.
As the revolution swirls outside its walls, even the Times is feeling fresher. “The average age of contributors when I started was in the low fifties,” Shortz estimates. “Now the average age is in the upper thirties.” In June, a Sunday puzzle from Agard called “Stoners’ Film Festival” included a number of entries with a particularly green shade of double entendre: PUFF PIECES, JOINT RESOLUTION, HIGH DRAMA. That same month, LESBIAN and MANSPLAINED both made their debuts. Some of the “mini” and “midi” puzzles that the paper sells through its Crosswords app are written by women, constructors of color, and those from the LGBTQ+ community, thanks in part to outreach by Shortz’s deputy editor, who’s 26. As Shortz himself says, “the themes are more interesting; the voice in the puzzles relates more to real life.” Which, in turn, means that the audience gets broader as well—but not that the kibitzing will ever stop. Even “Stoner’s Film Festival” had its detractors. “Should have been used for rolling paper,” one solver sniffed in a comment. “And to think I thought that things were starting to look up for Sundays.”
Some things never change.
PETER RUBIN (@provenself) is WIRED’s senior correspondent. He wrote about The Lion King’s virtual filmmaking in issue 27.06.
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