How the New York Times Crossword Became Too Big to Fail

Despite decades worth of missteps and competition from a growing indie scene, the Times puzzle is slow to change.

by | January 22, 2021

Will Shortz has been at the helm of the New York Times Crossword for nearly as long as I’ve been alive. Since 1993, the world’s most famous word nerd has meticulously turned his love for crosswords into an empire — the Times’ standalone crossword subscription, which he edits, crossed 600,000 paid subscribers in 2019. There is nothing else like the Times Crossword, but besides its monopolizing influence, the most enduring narrative about the daily puzzle, and Shortz’s editorship, is its long history of missteps on matters of race, gender, and sexuality. In the last decade, ILLEGAL has been used to describe someone ”caught by border patrol,” THUGS has been the answer to the clue “gangsta rap characters,” and an anti-Hispanic slur was used as an answer to “pitch to the head, informally.” The word NOOSE, used 69 times since Shortz took over as editor, has been clued as everything from “it may be left hanging” in 2013 by Jeff Chen, the blogger at the helm of crossword site xwordinfo, to “end of a hangman’s rope” this past April. In June, as police brutally suppressed Black Lives Matter protests around the world, TASE was included in a puzzle along with the clue: “Stun, in a way.” It was the 32nd time the word has appeared under Shortz’s editorship.

Every word that makes it into a crossword puzzle is a carefully curated choice, greenlit by both author and editor. The history of missteps is well-documented, and constant calls for more diversity in Times crossword clues, words, constructors, and editorial leadership have soundtracked the sections’s meteoric rise for years. But change has been incremental. One white, male editor became three white, male editors as Joel Fagliano and Sam Ezersky joined Shortz at the helm as assistant and associate puzzle editors, respectively, in 2014 and 2017, with Fagliano now serving as digital puzzle editor.

For years, the slow pace of change was tolerated, but the puzzle making community’s collective patience ended on March 27 of last year when the “Letter to the Executive Director of Puzzles at the New York Times” was published. Now signed by nearly 600 constructors and solvers, it detailed the discrimination and bias of the Times Crossword and was pegged to two major developments in the crossworld. First was the publication of Natan Last’s The Hidden Bigotry of Crosswords for The Atlantic, which described “the systematic erasure of minority voices in puzzles written by women, people of color, and queer constructors.” 

The second issue was the story of crossword test solver Claire Muscat’s experience of systemic sexism at the Times, which led to her resignation. According to the letter, Muscat had been told “her ‘primary role’ was to be a female censor” and that “she was hired to check for content that might be offensive to female solvers [and] asked not to offer advice or feedback outside of that identity-based purview.” After the letter was published, constructor Elizabeth C. Gorski, who had published over 200 puzzles at the Times, also spoke out about the sexism she encountered that led her to quit submitting puzzles in 2015. “I no longer could support a newspaper that, year after year, failed to publish women constructors in equal numbers with male constructors. During my tenure at the NYT, gender parity was never reached. It still has not been achieved. Far from it.”

After laying out the issues with the Times Crossword, the letter made three specific demands: constructors should receive access to the proofs of puzzles before they go to print; women and non-binary people should comprise at least half of Shortz’s test solving team; and the Times must make a public commitment to adding diversity to its editorial staff. Almost immediately, constructors were given access to proofs before their puzzles were published. In June, the Times began the search for new crossword editors and by September, Wyna Liu and Tracy Bennett — two female constructors with deep ties to the indie crossword community — were named as associate puzzle editors. Late last year, Everdeen Mason, a Black woman, joined the Times as editorial director of Games, a section that includes the crossword. For those with just a passing interest, it may be difficult to grasp how seismic the shift could be, but for many in the community, the letter felt like a turning point.

No crossword puzzle, no matter how niche the hobby itself may seem, exists in a vacuum. To fully understand how much these three demands would transform the Times Crossword, you have to know just how broken it was allowed to stay for so long. The puzzle hasn’t always been a money-making machine despite all of its cringe-worthy missteps. How it became too big to fail — and what can be done to finally fix it — begins with how The New York Times came to dominate the crossworld. 

The first mention of crossword puzzles in the New York Times appears in 1924, when the publisher described the crossword as a “sinful waste” of time and energy. Five years later, the Times declared that “the cross-word puzzle, it would seem, has gone the way of all fads” in a piece titled “All About the Insidious Game of Anagrams,” another game they were not a fan of. It would take the bombing of Pearl Harbor on December 7, 1941, to change their minds. On December 18, Sunday editor Lester Markel sent a letter to publisher Arthur Hays Sulzberger suggesting that, in the context of America’s entry into World War II, the Times “ought to proceed with the puzzle” not just as an antidote to the overwhelming despair of reading the news, but also a way for people to occupy themselves as they huddled in bomb shelters. Attached to his memo was a note from Margaret Petherbridge Farrar, a pioneer in the crossword industry. “I don’t think I have to sell you on the increased demand for this type of pastime in an increasingly worried world,” she wrote. “You can’t think of your troubles while solving a crossword.”

On February 15, 1942, the first-ever Times crossword was published under Farrar’s watchful eye. As the Times became the last major metropolitan daily newspaper in the country to offer a crossword puzzle, she became the first, and only, head puzzle editor at the publication. For 27 years, she edited every puzzle and worked to increase the number of female constructors — 35% of constructors during Farrar’s tenure were women, according to Shortz’ estimates. Under her leadership, Farrar helped establish the Times Crossword as one of the nation’s best before being forced out by the publication’s mandatory retirement age of 70. Her replacement was the Metro desk’s Will Weng, picked for the job solely because he was the only person in the newsroom who knew anything about puzzles other than Farrar. It was under Weng that “a sense of humor and playfulness” made its way into the grid — playfulness that would soon be snuffed out by his successor.

In 1977, former school superintendent Eugene T. Maleska took over and turned the crossword into an intellectual litmus test stuffed with references to Latin and opera. It was during the Maleska era that an ideological rift began to form between the old guard and a new wave of constructors and solvers, a rift that exploded in 1988’s “oreo war” fight over how to clue the word OREO. The old guard preferred “mountain: prefix,” which referred to “oreortyx,” or mountain quail. The newer generation? They just wanted it to be “cookie.” It was in that same year that Shortz, then the senior editor of Games magazine, called the crosswords published under Maleska “stiff, pedantic, humorless, and old-fashioned.” 

When Maleska passed away in 1993, the stodgy legacy of the old guard ended and, with the announcement of Shortz as his replacement, a new era began. Even before taking over at the Times, he was a crossword legend in the making. Born to Arabian horse farmers in Indiana in 1952, crosswords were Shortz’ lifelong passion. He sold his first puzzle at the age of 14 and became a regular contributor to Dell puzzle publications by 16. In college, he designed his own major in enigmatology, or the study of puzzles, becoming the only person in the world to be an academically accredited puzzle maker. In 1978, a year after Maleska took over the Times Crossword, Shortz began working for Games magazine and founded the American Crossword Puzzle Tournament, a Super Bowl for word nerds.

Under Shortz, the Times Crossword flourished, bringing more pop culture and fun to the black-and-white grids. He, too, has become a pop culture icon, appearing as himself in episodes of The Simpsons and How I Met Your Mother. In 2006, the crossword documentary Wordplay cemented his status as a celebrity — it featured everyone from Jon Stewart and Bill Clinton to the Indigo Girls praising his work. But with this celebrity status came protection from criticism. Beyond the well-documented pattern of bad decisions under his editorship, the Shortz era has also been defined by an archaic obstacle course of challenges for constructors that have put walls around the pastime. 

Before last year’s open letter finally forced the Times Crossword to change its ways, submitting a puzzle meant sending it by postal service to Shortz, who has worked from home in Pleasantville for decades instead of commuting to the office. Shortz is not the only high-profile editor to have the freedom to work from home, but for interns at the crossword department, this habit often meant sleeping on Shortz’s couch. According to constructor Nate Cardin, “at least three of Shortz’s interns have lived at his home in Westchester while working for him.” For constructors whose puzzles were accepted, it was standard practice — before the open letter forced the cessation of the practice— for a puzzle to have up to half of the clues changed during edits. These edited clues would appear in the paper without the constructor’s input or approval. For any constructor wanting to diversify into their grid, the lack of dialogue with the editor meant that it could be released under their byline with something offensive or racist they had no part in writing.

Not only did the opaque editing process serve no real purpose, it also created an unnecessarily long timeline between submission and publication, especially for new constructors. For Yacob Yonas, a puzzle maker who was included in 2019’s Black History Year Midi Pack at the Times, “the feedback loop is so long that it burns people out. For somebody who’s new and upcoming, why do they want to submit it somewhere where they’re going to wait three months to get a no?”

The problem with the Times Crossword goes far beyond just this archaic process: Any scenario where three white men decide what is culturally relevant is a recipe for disaster. Shortz deemed himself an “arbiter of what’s significant” in a 2018 episode of Real Sports with Bryant Gumbel, a quote has come to encapsulate the problems with the Times Crossword’s homogenous leadership. “The only way to live up to that title for anybody — [and] I don’t think it is possible to [do so] — is to have a foot in every sphere of significance,” Sid Sivakumar, the puzzle constructor behind Sid’s Grids, told Study Hall. Sivakumar has taken to calling this “lexical gatekeeping”: the fact that the lexicon of the editor informs what goes into the grid and what is left out.

Lexical gatekeeping is by no means limited to the Times. Any crossword that requires an editor will ultimately rely on the editor’s vocabulary, and arguments over cultural relevance are going to happen at every crossword department. The problem arises when the editorship does not reflect a diverse array of perspectives, and it is compounded when “relevance” is determined by whether or not something is “mainstream.”

To their credit, diversity in the Times’ roster of crossword constructors has improved, but change has been incremental. There was a Black History Year Midi pack (“Midi” refers to medium-sized, 9×9 grid puzzles) featuring constructors of color, and in 2020, they kicked off Women’s History Month with a week of all-female constructors, but featured only one who was non-white. “It was very noticeable to me that it was six white women. It wasn’t progress to me,” New Yorker constructor and film critic Kameron Austin Collins told Study Hall. “You could have found seven women constructors to do seven different puzzles in a week. That’s not something that the Times couldn’t have done for some time now.” For Sivakumar, these small instances of diversity in both clues and constructors are “no better than a network sitcom that has all-white actors and has maybe one or two token Asian or Black or Hispanic actors.”

One financial incentive for the Times’ lexical gatekeeping is its efforts to be timeless, allowing puzzles to be reproduced years later. Beyond its subscription service, the Times Crossword has built a market of standalone crossword books syndicated from years past. As writer Oset Babür noted in an interview with constructor Paolo Pasco: “Shortz prefers evergreen crosswords that won’t go stale if he decides to include them in future puzzle books.” There is a solid financial logic in keeping puzzles as general as possible to repackage later, but in practice, to generalize a puzzle is to privilege references familiar to an older, whiter audience. Collins argues this isn’t the only way to conceive of widespread knowledge:“For people on the margins, in order to survive in any kind of mainstream culture, you do have to know white culture to a degree, but you also value other cultures and see other cultures as constitutive of general knowledge.” 

Over hours of interviews with half a dozen Black, South Asian, and queer constructors, every person talked about not feeling represented as a minority when they first encountered the Times Crossword. For Alex Briñas, an emerging constructor on the scene, it began with a feeling that she wasn’t smart enough for the puzzle, but she soon realized the problem wasn’t her — as a queer woman of color, the clues were designed for a target audience far removed from her world. Beyond a lack of relevant text, there were the racist clues: one on New Year’s Day 2019 came up in every conversation I had. In that puzzle, the word BEANER, used as a slur against Hispanic people, was clued as “Pitch to the head, informally,” a reference to baseball players being hit in the head with a baseball. The backlash was so immediate and intense that Shortz issued an apology the same day, saying that he and his assistant editor, Joel Fagliano, had never heard the word used as anything but a baseball term. “Maybe we live in rarefied circles,” Shortz wondered, before explaining that any “benign meaning of a word is fair game for a crossword,” even if it happens to also be used as a slur. “Perhaps I need to rethink this opinion, if enough solvers are bothered.”

Even by our modern Notes app apology standards, it was weak. The problem wasn’t only that Shortz admitted to living in a “rarified circle” and only committed to rethinking his opinions if “enough solvers are bothered” — it’s that this wasn’t even the first time he’d apologized for an anti-Hispanic slur making it into a puzzle. In 2012, after “one caught by border patrol” was clued by Shortz himself as ILLEGAL, he issued an apology but, just as he would seven years later, he fell back on the same defense. “I had no idea that use of the word ‘ILLEGAL’ in this sense (as a noun) was controversial.” In 2014, after calls for more gender diversity at the Times to rectify the drop in female constructors during the Shortz era, he responded with indifference, saying: “I don’t think it matters. Men like to do some things more than women, and women like to do some things more than men. I say let’s celebrate our differences and move on.” Six years after these sexist comments, not much has changed in terms of both constructors and the content of puzzles. According to an ongoing tally by puzzle solver Matt Gritzmacher, only 25% of the puzzles published by the Times in 2020 have been by women, non-binary, or gender non-conforming constructors. In a report by The Pudding on the clues and answers in Times crosswords in 2020, only 36% were about women, and only 28% were about minority racial groups. 

It’s no wonder that so many constructors whose introduction to crosswords was through Shortz and the Times have felt alienated. But while some may set the crosswords down and move on, others have taken the lack of diversity at the Times as a challenge. After Nate Cardin became fed up by the “super-hetero-patriarchal” words and clues in the Times crosswords, he put out a call to other queer constructors asking to make their own puzzles. This was the origin of Queer Qrosswords, a series of puzzle packs made by LGBTQIA+ constructors, that has raised over $45,000 for LGBTQ+ charities since 2018. 

With the project, Cardin joined an indie crossword scene that has been growing for years into an exciting, incredibly diverse antidote to the Times. A year before Queer Qrosswords launched, Deb Amlen linked up with Amy Reynaldo and Patti Varol to start Women of Letters, a puzzle pack that raised money for women-centric charities, and in 2019, inspired by Women of Letters, Laura Braunstein launched The Inkubator, a subscription service that publishes three puzzles a month by cisgender, transgender, and women-aligned constructors. 

Among the most notable projects in this realm are the Indie 500 crossword tournament, which began in 2015, and Ben Tausig’s American Values Club Crossword (AVCX), a reincarnation of the canceled Onion AV Club crossword, which has been has been fully independent since their 2012 Kickstarter helped raise $26,000 for the project. For many constructors, AVCX is a gold standard both for their high-quality puzzles and for their business model, which is transparent about the fact that most of the money goes into the pockets of constructors. The indie scene has become a thriving incubator for a new generation of crossword makers poised to diversify the industry, and nowhere is that more apparent than with the rise of Erik Agard. 

It was a 2013 profile in the Washington Post that introduced Agard to readers far removed from the crossword crowd. At the time, the biracial, 19-years-old African American studies major had already become a celebrity in the crossword scene for his lightning-fast puzzle solving skills, a fact that made the shy teenager uneasy. He was declared “the future of speed solving” by Michael Sharp, who runs the influential Rex Parker crossword blog, and in the years that followed, Agard racked up a list of achievements that rivaled Shortz’s reputation in the 1970s as a wunderkind. He co-organized the Indie 500 tournament in 2015 and won the Lollapuzzoola crossword tournament in 2016. In 2018, he won Shortz’s long-running American Crossword Puzzle Tournament, won more than $66,000 across three Jeopardy! Games, and appeared on Bryant Gumbel’s “Real Sports” program (the same episode that featured Shortz declaring himself the “arbiter of what’s significant”). A year later, Agard was named the USA Today’s new puzzle editor, cementing his status as a leader of the new guard for the crossword industry.

Beyond his skills as a crossword solver and constructor, Agard is also well-known in the indie community for his mission to mentor as many constructors from diverse backgrounds as possible. New constructors I spoke with, including Yacob Yonas and Alex Briñas, cited Agard’s help as the reason they had started constructing. It was Agard who created the Crossword Puzzle Collaboration Directory, a Facebook group made to rectify inequalities “for women, people of color, and folks from other groups underrepresented in the puzzle world.” (As helpful as that group has been, it still places the burden of fixing diversity problems on constructors willing to offer their help, which lets systems like the Times maintain their unnecessarily high walls to puzzle publishing.) In 2019, some of Agard’s work as a mentor came to fruition at the Times with their Black History Year Midi Pack. Beyond just turning Black history into a set of puzzles, it also served as an unintentional snapshot of the range of Black talent in crossword construction. Alongside newcomers like Yonas and stars like Agard was Jan Buckner Walker, a veteran constructor who has been on a steady, decades-long mission to diversify both the crossword and the audiences who solve it.

The effort began in 2003, when Walker launched Kids Across, Parents Down in the Washington PostThe project turned crosswords from a single-solver, solitary pursuit into a group exercise, and it was endorsed by Shortz himself, who, she recalls, told her it was a gateway to the love of words, the love of language, the love of wordplay. Walker shared her excitement that it brings people to crosswords “with more confidence, more joy.” For Walker, it was just the beginning. Six years later, she launched Kids Across, Teachers Down to bring the crossword to the classroom. 

While these two projects helped to bring crosswords to a young audience, her biggest contribution to the crossworld may have been the launch of a crossword section for both Essence and Ebony. Speaking of her time creating crosswords for Essence, Walker recalled the challenge of getting young, Black readers interested in a word game that, at other outlets, would generally only cater to them during Black History Month in February. “I’d hear from young people saying, ‘I’ve never had a crossword that was about me, that celebrated me, or interested me at all.’” Some devotees of her Kids Across, Parents Down projects were thrilled to find out she was a Black woman at events. “They’re like, ‘Oh, my God. You’re Black! Come, kids, come over here.’…For Black people, that’s a huge shot in the arm.” 

Her contributions to the crossword community have helped pave the way for a new generation of forward-thinking editors who, in the past few years, have risen through the ranks at major publications around the country. One such person is David Steinberg, a prodigy who became the youngest crossword editor of a major newspaper ever at the age 15, when he started working for the Orange County Register’s 24 affiliated newspapers. By the end of 2018, when he was just 22 years old, Steinberg was named editor of Universal Crossword, a syndicate of the Andrews McMeel Universal media corporation, and began the Universal Crossword Equal Representation Project (UCERP), a program that matches mentors with new constructors who are women, people of color, and members of the LGBTQIA+ community. The result was immediate. In June of 2019, 40% of the Universal Crossword puzzles published were written or co-written by women, compared to an average of 19% per month from January to May of that year. 

Outside of the Times Crossword orbit, a shift is occurring in the pastime’s perception and audience. In the last year, Agard has turned the USA Today crossword into a radical and exciting destination for crossword solvers. Most constructors are women, and many are Black, Indigenous, and people of color. Puzzles are full of references to Black culture, notable women, and queer culture. As Sivakumar noted: “It’s not simply the fact that [Agard] has tapped into a diverse group of constructors to make the puzzle for USA Today. It’s also that his clueing style espouses cultural diversity and cultural sensitivity. He’s bringing a totally different and fresh style of clueing that we haven’t seen from mainstream venues in a long time.”

In tandem with Agard’s transformation of USA Today, constructors I spoke with universally pointed to The New Yorker’s crop of crossword editors as a new gold standard for diversity. Since launching the crossword in 2018 with a once-a-week puzzle, it has surged in popularity; in 2019, they added a second weekly puzzle and hired Liz Maynes-Aminzade as puzzle and games editor, the first female puzzle editor at a major publication since Farrar at the Times. In 2020, they added Partner Mode, a third weekly puzzle, and three new editors, adding to a powerhouse group of constructors that now includes Collins, Agard, Wyna Liu, Elizabeth C. Gorski, Natan Last, and Anna Shechtman, a former intern of Shortz who was one of several authors of the open letter to the Times that rocked the crossword community in April. It was also Shechtman who helped recruit the new roster of constructors at The New Yorker. As she told WIRED in 2019, the goal was gender parity and diversity. “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.”

Publications like the USA Today and The New Yorker, as well as a thriving indie scene, have become a roadmap for a more equitable crossword industry. When talking to constructors about how to modernize and diversify the community, one of the most pertinent points came from Sivakumar, who has become an outspoken critic of the scene’s issues. With the recent explosion of indie publishing, it has become clearer than ever that you no longer need a high-profile editor to make good puzzles — you probably never did — but he believes that going it alone also doesn’t feel like the best way forward for the crossword industry. Indie constructors have shown how adept they are at writing clues, editing grids, and publishing entirely on their own, which doesn’t bode well for a system that puts all the power in the hands of editors who deems themselves the arbiter of significance. But much like the ongoing discussion over the Substackification of journalism, having a second set of eyes on your work will always be helpful.

The problem in crossword construction isn’t editing: it’s that white, male superstar editors like Shortz decide what is culturally relevant. Just like the downfall of “Dude-itors” (not coincidentally also white men) who used to be as famous as the publications they ran, the reckoning over who gets to control what goes into a Times crossword is overdue. Words matter and, as Sivakumar reminded me, people can and do learn new things from crosswords: “Everything that we’re familiar with was only shared with us through some media. So why should crossword puzzles be any different? It’s just another medium with which to share things with people.”

This clamor for a more diverse Times Crossword has been years in the making, guided largely by indie constructors. But by speaking out, they risk alienating the the most powerful employer in the business. For many, like Collins and Cardin, keeping a foot in the door at the Times is essential. “It is the gateway puzzle. It is the cultural institution puzzle,” said Collins. “No other puzzle is going to come close to that kind of cultural relevance, and I don’t want all of us who are interesting and different to flee from that space.” A shoutout from the Times’ Wordplay column landed Sivakumar a bunch of new followers on his mailing list, and validation from the Times can boost many other small constructors. “Sometimes [indie constructors] do have a symbiotic relationship with mainstream publishing, and we’re very happy for that. We’re not adversaries in any way,” he noted. The indie puzzle scene has bloomed in part from constructors appearing on the Times, but by relying in part on that exposure, it means constructors can only rock the boat so much.

Perhaps most importantly, it’s unclear that the Times Crossword wants to change at all given their financial dominance. Despite all the missteps, the archaic editorial process, and the lack of diversity, Shortz has built an empire. They’ve introduced more games, created Mini and Midi packs, and patted themselves on the back for having a week’s worth of female constructors for Women’s History Month, a band-aid for the fact that the proportion of female constructors has decreased significantly in the Shortz era and pales in comparison to other publications. As Gritzmacher’s meticulous spreadsheet reveals, the 25% of Times puzzles by women, non-binary, or gender non-conforming constructors in 2020 looks paltry compared to the New Yorker’s 50% and USA Today’s 69%.

In the wake of the letter to the Executive Director, the Times has made commitments to diversify and, months after promising more female and non-binary puzzle solvers, they announced two new associate puzzle editors in September: Inkubator co-founder Tracy Bennett and New Yorker constructor Wyna Liu, who counts Agard as one of her mentors. In December, they announced that Everdeen Mason would be their first-ever editorial director of the Games section.  The push for diversity in editorship is appreciated and, according to stats from Gritzmacher’s spreadsheet, more non-male constructors are having puzzles published. But it’s too soon to tell whether this will be a small blip or a meaningful change. Beyond the pledge for gender diversity and “expanding and diversifying the editorial team,” the Times still hasn’t publicly addressed the lack of constructors of color or committed to more racial diversity in the words and clues of puzzles. All the while, their subscription base has grown to astronomical levels. As Agard noted in a recent Time interview, “the bar is on the floor” when it comes to diversifying crossword puzzles.

Publications like USA Today and The New Yorker and projects like the American Values Club Crossword, Queer Qrosswords, and The Inkubator — who announced a partnership with Marie Claire in September to publish crosswords in their print issue — are providing a roadmap for a culturally rich crossword world, but roadmaps are only useful if an industry chooses to follow them. As Cardin pointed out: “If you have all this privilege, what good is it unless you use it to kind of disrupt the system?” It’s a question that applies not just to the crossword industry, but also to the entire media ecosystem. If an editor is too big to fail because they are more talented at making money for their company than at creating a culturally relevant product, the biggest loser is the consumer. The Times Crossword is taking steps towards fixing their bad habits, but it took a public call-out and years of criticism to effect change. The fact is, when you’re at the helm of the Times Crossword, you both build the system and decide how much to change it. With that much power in one institution’s hands, what other options do marginalized constructors have besides asking to be seen and hoping to be heard?

Subscribe to Study Hall for Opportunity, knowledge, and community

$532.50 is the average payment via the Study Hall marketplace, where freelance opportunities from top publications are posted. Members also get access to a media digest newsletter, community networking spaces, paywalled content about the media industry from a worker's perspective, and a database of 1000 commissioning editor contacts at publications around the world. Click here to learn more.