At only 17 years old, Owen Bergstein—a Boston University Academy senior—won his division at the annual American Crossword Puzzle Tournament.

Student Life

This BU Academy Senior Is Paving the Way for Young People in the Puzzle World

Owen Bergstein recently won his skill division at the annual American Crossword Puzzle Tournament

Hot summer days may bring back memories of operating a lemonade stand or washing a neighbor’s car for a little extra spending money. But for 17-year-old Owen Bergstein, a rising senior at Boston University Academy, his summers have looked quite different: he’s spent them peddling miniature magazines, complete with hand-drawn comics and crossword puzzles. 

While others may have abandoned their “business” at the end of summer, Bergstein has continued to pursue his love of crosswords. The young crossword constructor’s audience has expanded from neighbors, friends, and family to readers of the New York Times, the Los Angeles Times, and USA Today. And this spring, he competed at the American Crossword Puzzle Tournament in Stamford, Conn. With a record 889 contestants, Bergstein finished 19th overall in New England and 135th nationwide, one of 175 contestants who solved all seven crossword puzzles with no mistakes.

“I have always seen words as units for word play,” Bergstein says. “My family had a subscription to the New York Times. When we would get the print edition delivered, I would rush to the puzzle page. At first, I was only able to solve the Monday puzzles, then I could solve the Tuesday puzzles, and so on. I haven’t stopped since.”

Puzzles have always been a part of his life, he says. Road trips were spent playing anagram license plate games, and he remembers hearing how his mother constructed crosswords to send to the New York Times in the 1990s. His interest in crosswords never wavered, and now, years later, he is still pursuing his passion. “I probably solve a few thousand puzzles a year,” he says. “I’m also always creating a puzzle. I’ve probably constructed the grids for about 400 to 500 puzzles, and drafted the clues for about 100 to 200.”

Bergstein specializes in themeless puzzles, drawing inspiration for clues from pop culture, queer culture—even ideas that come to him in his sleep. He’ll put on a podcast—or a series of podcasts—and spend hours crafting puzzles, throwing most of them out until he feels an attachment to it. It isn’t unusual for him to spend 12 hours at a clip working on a puzzle, he says. The longest he has spent on a single puzzle? About 40 hours, he estimates—spread over multiple sittings and with a collaborator.

“Many mainstream publications have puzzles aimed at people probably four decades older than me, and puzzles traditionally have been made by mostly cisgender, heterosexual white men,” Bergstein notes. “My idea is to make puzzles that speak to people who aren’t that typical audience. I always want to make sure my puzzles can speak to everyone, while still being mine.” 

He began submitting his crosswords for publication in late 2022, and after “a lot of rejection,” he says, his first crossword was published in February 2024 in The Puzzle Society’s The Modern Crossword (since discontinued). From there, his dedication to crafting thoughtful puzzles has landed him spots in numerous publications, including, in a December 2024 debut, the New York Times, which marked Bergstein’s 10th published puzzle that year. 

While he’s focused more on the creative process of puzzling, recent competition victories have made him take tournaments a bit more seriously. In April he attended this year’s American Crossword Puzzle Tournament. It was his second time at the tournament, and he regards those weekends as some of the best of his life. Bergstein didn’t win last year, but was content to simply “nerd out” with other crossword connoisseurs, he says. He went into this year’s competition with similar expectations—and was stunned when he netted a divisional win. 

Bergstein doesn’t just compete in tournaments. One of his puzzles was selected for the 2024 Boswords Crossword Tournament, and as a Boston-based constructor, he was invited to be a judge. And while he says it was bizarre to see competitors take three minutes to solve a puzzle that took him hours to construct, the experience is among his career highlights. 

“We would collect papers from contestants and bring them to the judges’ room, and one of the contestants wrote a note at the bottom of the crossword,” he says. “You might be expecting, ‘Hey nice puzzle,’ but the note was filling us in on the news. I will never forget it, because that’s how I learned that Joe Biden had dropped out of the presidential race—someone wrote that in a note on my puzzle.” 

Despite his accomplishments, Bergstein says his proudest moment has been the release of his blog “Dissonant Grids,” an artistic take on crosswords featuring unpleasant and cathartic puzzles. After an analysis of his first puzzle, “Healing?”—which dealt with themes of grief—from professional crossword constructor Will Nediger, Bergstein’s idol, he says he finally felt seen as a creator.

As a queer youth in a field dominated by those much older than him, he says his passion for puzzles can be a lonely pursuit at times. But vast online forums and chat platforms like Discord have helped him to learn, grow his community, and even collaborate with constructors he admires. He hopes to see more young people in the puzzle world, and he thinks ventures like the New York Times’ Wordle or Connections are a step in the right direction. 

“I have such a long list of goals for the future. I would love to edit somewhere at some point—it’s the number-one thing on my bucket list,” Bergstein says. “I’d also love to expand the blog and bring on guest constructors. I just want to learn as much as possible and always have crosswords as a side project.”