Language, Logic, and Storytelling: Behind the Scenes at ‘The New York Times Crossword’ With Editorial Director Everdeen Mason

An anchor of word games across history, The New York Times Crossword is filled with eccentricities and livelihood. In a conversation with its Editorial Director, we are guided through the puzzle’s past, present, and future.

From+paper+to+digital%2C+The+New+York+Times+Crossword+has+evolved+throughout+the+years.+Nonetheless%2C+its+core+values+stay+close+to+the+first+ever+puzzle%2C+published+in+1942. / Flickr

From paper to digital, The New York Times Crossword has evolved throughout the years. Nonetheless, its core values stay close to the first ever puzzle, published in 1942.

“Keep the crosswords coming,” Former U.S. President Bill Clinton wrote in a 2002 letter to Will Shortz. “Even when I can’t finish them, they’re the only part of The Times that guarantees good feeling!”

William F. Shortz is the editor of the renowned New York Times Crossword, a position he has proudly held since 1993. Today, the letter sits in a frame outside his home office.

Since its inception on February 15th, 1942, the New York Times Crossword has been a sign of continuity throughout the last century, overseeing rapid societal changes and subtly weaving them into its black and white tiles. From constructing his first puzzle to editing thousands of guest submissions, the long-standing editor emphasizes one virtue for the Crossword: timelessness.

Where It Started

After the world’s first crossword in 1913 surged in popularity among readers, the New York Times initially refused to follow suit. Some columnists denounced the puzzle as a “primitive sort of mental exercise” and even a “sinful waste” of time, while others simply projected its decline and eventual disappearance.

This ideal was quickly reversed. Less than a year after the devastating 1941 bombing of Pearl Harbor, editor Lester Markel, along with the support of crossword pioneer Margaret Farrar, proposed the first New York Times Crossword as a form of World War II relief to American readers.

Albeit the last major newspaper in the world to implement a daily crossword puzzle, the Times caught up rapidly. With Margaret Farrar as its first editor, the Crossword drew in passion everywhere, from serving as a war distraction to becoming an essential cornerstone of American culture. 

Since then, only three other editors have oversaw the Crossword: Will Weng (1969–77), Eugene Maleska (1977–93), and Will Shortz (1993–present) — all of whom together have sparked a revolution. Each editor has added their own quirks and humor in the themes of the puzzle, in effect ensuring a wave of continuous creativity and innovation. Shortz, in particular, directed the first American Crossword Puzzle Tournament, facilitated the creation of the digital NYTimes Crossword, and coordinated Wordplay, a 2006 crossword documentary.

Today, the New York Times prides its crossword as the most famous in the world, with over 500,000 regular subscribers. Every day, a team of editors release a new puzzle that progressively gets more difficult throughout the week. A regular weekday puzzle is 15 by 15 squares, and typically has around 60 clues and answers. The Sunday crossword, on the other hand, is the biggest, measuring 21 by 21 squares and having almost 120 clues and answers. Contrary to popular belief, Sunday crosswords are only around midweek difficulty (around the same as a Thursday). Instead, Saturday claims the most puzzling spot.

Where It Is Now

To learn more about what goes on backstage in the newsroom, I interviewed Everdeen Mason, the Editorial Director at the New York Times Games. Aside from the Crossword, the Games editorial team also handles games like Spelling Bee, Wordle, Vertex, and more.

Here is the entrance to the New York Times skyscraper in Times Square, where millions of writers and puzzlemakers convene to put together stories of worldwide influence. (Spencer Sembrat / Unsplash)

“There is no ‘typical’ day at the Games,” said Mason. “Every day is chaotically busy, and we consistently spend the most hands-on time editing the Crossword.” 

The Times gets around 150-200 crossword submissions per week through a digital portal. After a team of editors sort through all submissions, reject many, and send some to a ‘pending’ folder, the whole newsroom gathers for review. 

Each submission is reviewed holistically, where the team takes into account every detail: the overarching theme, the “cleverness” of clues and answers, the setup of the puzzle grid itself, and more. Once a submission is approved, it is scheduled into a queue far down the line for editing and eventual publication.

There are four key stages to Crossword editing. The first edit for pending submissions is typically done by Joel Fagliano, who also creates the Mini Crossword daily. Since Fagliano is currently on parental leave, many other staff members have edited these submissions and even made Mini Crosswords, including Mason herself.

Afterwards, the puzzle travels to Will Shortz for a second edit. A fact checker then edits it a third time, all before sending it back to the original puzzlemaker and other testers for the final seal of approval. 

This year, Mason has organized a major change in the editorial process: going entirely digital. “Before this transition, the crosswords were paper files at Will’s home,” she explained. “Making the editing process digital not only reduces time and improves accessibility for the team, but allows for more input and transparency as a whole.”

Now that the team has followed in the footsteps of the digital age, these transitions have brought both convenience and criticism to the Crossword. From puzzle design programs to word databases, many constructors have found the creation process becoming much easier. Meanwhile, others have voiced concerns about the use of algorithms in traditionally paper puzzles like the Crossword, saying that it defeats the original “by the people, for the people” culture.

“As someone who works closely with audience strategy, I think that information architecture is a lot more widespread and all-encompassing than we may expect. Of course, algorithms are constantly trying to replicate how people are interested in things, which is an inevitable product of technological innovation and corporate greed,” Mason said. 

Ultimately, however, the Crossword’s lifeblood is made up of the people: its constructors, editors, and players. Looking beyond its digital transformation, each step of the process is still carefully examined by an individual — only with computer keys instead of a pen. Even if the puzzle’s purpose has long shifted from war relief, many of its original values still ring true today.

“Every crossword tells a story,” continued Mason. “Each one is made by a person who is trying to say something and reflect their world. Solving a crossword puzzle is like having a conversation with the constructor, especially if they choose strange themes that you can eventually ‘tease’ out.” 

Despite being the most time-consuming and editorial-heavy part of the New York Times Games, all of the work pays off when the Crossword finally gets to the reader. Editors and players view the Crossword as two sides of the same coin, where one side is a complex backdrop and the other showcases the performance in all its splendor.

“My grandmother has been solving the Crossword for years, ever since paper puzzles were the mainstream,” said Declan Hilfers ’22. “When I asked her why the Crossword has kept her playing all these years, she said, ‘Thankfully crosswords aren’t as complicated as life. Personally, I enjoy the satisfaction that comes from solving a crossword puzzle, and perhaps adding a new word to my vocabulary, like japes from this week.’ I think sometimes that’s the best way to sum it up.”

Where It’s Going

Although the New York Times Crossword remains timeless for many, it is gradually starting to take on a new theme as well: relevance.

“When I try to solve crossword puzzles, especially ones from the 2000s, I can almost never solve them entirely without looking certain parts up,” said Sarah Cheng ’24. “I feel like there’s a perception that crosswords are somewhat exclusively for older people, and I can see how that’s true when clues often allude to entertainment from the 1970s or 80s I’ve never even heard of.”

At the end of the day, crossword constructors and editors need to think about their real-world impact. What themes are worth knowing and validating to players? What are people sensitive to? Is a player going to be glad when they finally figure out an answer?

The Crossword community is incredibly vocal and reliant on diverse artistic expression. “Aside from coordinating across the newsroom, one of my other key responsibilities is to advocate for the team and their creative freedom,” Everdeen Mason (pictured at top), the Editorial Director at the New York Times Games, said, during a Zoom interview that I conducted with her. (Charlotte Zhou)

“We need to have a more modern, universal view,” said Mason. “Everyone starts at a different point on the puzzle, whether it be trivia, etymology, history, or pop culture. In my tenure, I hope to add more variety to the Crossword and to make it more fair, where everyone can unlock at least part of the puzzle — after all, if clues and answers only cater to one audience, then they lose their meaning of telling a story and being a collaborative experience.”

In fact, the Crossword newsroom has recently implemented a ‘Yellow Flag List’ in the editorial process. During individual and group review, if an editor sees something archaic or problematic in a puzzle that is not accessible to a wide range of players, the team must address and revise it. 

In a form of entertainment that utilizes the power of language and logic as much as the Crossword does, every clue and answer forces their players to think about words, meanings, and applications. Instead of allowing the Crossword to become a cultural barrier to some, Mason and her team are focusing on expanding the unity of words for all. 

“Things change all the time, so the future is still uncertain,” she laughed. “As of right now, what I’m mainly concerned with is getting the team through the end of the year without Joel here.”

“But in the long term, I hope the Crossword takes on a different personality.”

“Every crossword tells a story,” continued Mason. “Each one is made by a person who is trying to say something and reflect their world. Solving a crossword puzzle is like having a conversation with the constructor, especially if they choose strange themes that you can eventually ‘tease’ out.”