Cookie Duncan ’24 Cracks the Grid

The New York Times receives around 200 crossword puzzle submissions weekly, but it can only accept seven—one for each day of the week. This means submitters have a less than 4% chance of having their puzzles published. It takes some crossword constructors many years and countless rejections to make it into the Gray Lady, the paragon for all puzzlers. Kathleen (Cookie) Duncan ’24 did it in seven tries.

Duncan’s puzzle, published on Thursday, April 24, 2025, relies on a cheeky theme—“genre-bending”—that asks solvers to twist the lengthy names of niche book and film genres across multiple clues. (For example, use the 35-Across clue, “Lady Bird and Stand By Me,” and the boxes of 38-Down to spell out COMING OF AGE.) Duncan, an English language and literature and government double major who lived in Albright House, got the idea for the puzzle when she was reading her hometown library catalog and came across the term “genre-bending” in a book’s descriptive copy.

A native of Dedham, Massachusetts, Duncan became a serious crossword solver in December 2022, during the winter break of her junior year.

“In the ongoing, never-ending battle to not be on social media as much as perhaps one is inclined to be, I started using The New York Times Games app as a thing to do when I wanted to be on my phone,” she recalls.

The crossword helped her stay connected to her parents during the spring semester of 2023, while she studied abroad in Bath, England. She would send them screenshots of particularly difficult clues—usually sports trivia or pop culture references before her time—and rely on their help to maintain her solving streak. Once she returned to the States, Duncan would unpack the daily puzzle with housemates and friends.

“There would be discussion of it, but censored discussion, because what if someone hadn’t done it yet?” she says. “Sitting around in the common room, we would be doing it at the same time, but we couldn’t quite say what we had just entered. We’d just be like, ‘Oh, 42-Down is so hard today.’”

Duncan began reading Wordplay, the Times’s daily crossword column, and its comments, which led her down the rabbit hole into the realm of die-hard crossword enthusiasts. Soon she was learning solving tips and construction basics from users on the subreddit r/crossword and the Discord server Crosscord.

If you didn’t know that your daily crossword was usually created by a bevy of freelancers and hobbyists—heck, if you thought Will Shortz single-handedly made every crossword for The New York Times—you wouldn’t be alone. Crossword construction is a robust niche once you dig deep enough, but it does require excavation.

Puzzle builders use specialized software that can package each crossword in whichever file format their outlet of choice prefers. (The Times is hardly the only name in the game—Duncan has also submitted to The Atlantic, USA Today, and the Los Angeles Times. Apple News+ has published two of her puzzles: one in September 2025 and another in January 2026.) And there are norms to learn: For instance, submitting the same puzzle to multiple outlets at once is a no-no.

Duncan got serious about crafting crosswords in the fall of her senior year, and she submitted her winning puzzle to The New York Times in August 2024, just months after graduating. That November, she got an email from Times puzzle editor Tracy Bennett, who said the Games team liked the genre-bending theme, but they would need to see some substantial edits from Duncan in order to green-light the puzzle.

Duncan was undeterred by the caveat-ridden reply. “I was like, ‘Why would I mind?’”

New York Times Games editors don’t receive any demographic information from submitters, so when Bennett worked on Duncan’s puzzle, she had no way of knowing that it had been constructed by a then–22-year-old puzzle-making autodidact. When informed for the sake of this article, she described Duncan’s feat as “really impressive.”

Perhaps no one knows the freelance crosswording game better than Bennett, who joined The New York Times in 2020 based largely on her work as a freelance puzzle constructor and editor. Bennett co-founded Inkubator, a website dedicated to publishing puzzles by women and nonbinary constructors, and has had puzzles published everywhere from Bust magazine to The Chronicle of Higher Education. She had her first crossword published in The New York Times in 2013, after she had been constructing for about a year under the guidance of a mentor, professional crossword constructor Victor Fleming. Even with a mentor, it took a dozen or so attempts before Bennett had a puzzle accepted. “There were many rejections,” she says.

Duncan, who currently works as a library assistant at the Dedham Public Library—the same place where she got the inspiration for her New York Times debut—is thrilled with her crossword success, though wary of the pressures that come with monetizing any hobby. (Major publications pay for crosswords. The Times pays between $500 and $750 for a standard-size puzzle and up to $2,250 for Sunday crosswords.)

“I’d say it’s the same amount of fun, but now that I know that it’s not just a pipe dream to get published—and I know that if I work hard enough, it actually can happen—that’s in my head a bit more than when I was just like, ‘Let’s do this for fun and see if anything happens,’” Duncan says.

She has no intention of giving up crossword creation, but she says she might take up coloring pages too, to alleviate the pressure.

As far as The New York Times is concerned, Duncan is now a trusted member of its freelance pool. She’s already had a second crossword accepted, though its publication date has yet to be announced.

“We think of people as being in the community of our New York Times crossword puzzle constructors, and she’s solidly in there,” Bennett says. “She’s got good ideas, she’s creative, she seems to take feedback really well and grow fast. She’s just ideal.”

Lena Wilson ’16 is a writer based in Brooklyn, New York, where she lives with her wife and their two senior dogs. She majored in film studies and lived in Talbot House at Smith.

This article appears in the winter 2026 issue of the Smith Quarterly.