JCHS senior Nathan Hasegawa with his April 14 puzzle in the New York Times.
JCHS senior Nathan Hasegawa with his April 14 puzzle in the New York Times.

JCHS senior can’t solve crosswords, but just had one published in New York Times

For their yearlong capstone projects, seniors at Jewish Community High School of the Bay in San Francisco have engaged in all manner of pursuits, from learning a new skill such as baking or photography, to training for a triathlon, to volunteering in a retirement community. Nathan Hasegawa decided to try to master the art of crossword puzzle construction.

The 17-year-old Oakland resident set an ambitious goal of getting one of his puzzles published in the New York Times, the most prestigious puzzle platform in the United States — something that fewer than 50 teenagers have done since 1994, according to the Times’ puzzle master Will Shortz. And he wanted to do it before he graduates in June.

Hasegawa accomplished his goal with more than a month to spare.

His Times-worthy puzzle appeared on April 14, a Wednesday, meaning Shortz and his team considered it moderately challenging. (Puzzles get harder as the week goes on). The clues include nods to both his Jewish heritage (12 down: “Observe Yom Kippur”) and his Japanese heritage (13 across: “Dish that may be eaten with either chopsticks or a spoon”). Hints about the puzzle’s unique theme are scattered throughout this article.

“It was a long-shot goal to get a puzzle published in the New York Times,” Hasegawa said sheepishly in a Zoom interview. “I thought it would happen at some point, but I did not think it would happen so soon.”

He only began constructing crossword puzzles last August, using various online tools and databases to create the grids and come up with the “fill,” or the intersecting words in the grid. Surprisingly, he is not a puzzle solver himself because he said he has mostly eschewed popular culture, which is the basis for many clues. But “you don’t need to be good at solving them to make them,” he explained. “They’re totally different skills. If I don’t know something, I can just look it up. That’s not cheating when you’re making the puzzle.”

His parents, Andrea and Steve, inspired him to take up puzzle construction. They are avid solvers of the Times’ popular Sunday puzzle going back to their law school days at the University of Chicago. Andrea tested out each of Nathan’s puzzles and had a good feeling about the one that was ultimately accepted.

“It was really in the style of a New York Times puzzle,” she said. “We felt like he sort of got the hang of it over the course of the year.”

Nathan as a Temple Sinai preschooler in 2008, showing early signs of his talent.
Nathan as a Temple Sinai preschooler in 2008, showing early signs of his talent.

While Nathan may be relatively new to puzzle construction, Andrea said he has been creating games and trivia contests for his family since he was in elementary school. “We taught the kids how to play spades and hearts, and he made up a game called ‘clubs,’” she remembered. “It took a while to figure out his rules, but it actually worked and was really fun.”

Joshua Buchin, a Judaic studies teacher at JCHS who shepherded Hasegawa through different stages of his capstone project, said the two discussed alternate goals in case the Times rejected all of his submissions. But he was not surprised that Hasegawa did what he set out to do.

“The same kind of dedication that he brought to his crossword puzzles, he brought to everything he did” at JCHS, Buchin said. “It was amazing to see the pride that he took in what he had created, and his humility as well.”

The technical specifications for a Times crossword puzzle are extensive, and each puzzle is considered a collaboration between the constructor and the editors. Hasegawa said the editors tweaked most of his clues and added some of their own. The Yom Kippur clue was all his, though.

“I actually really liked that clue, not only because it was an homage to my school,” he said. “It’s also something that might trip people up.” (Hint: The answer is not the obvious “fast.”)

Hasegawa has been a little overwhelmed by the plaudits that have been pouring in from family, friends and online commentators. (One commentator wrote: “Wow — super cool puzzle! Very impressive debut for the young constructor. Looking forward to more from him.”) He intends to donate the $500 he earned for the puzzle to the St. Anthony’s Foundation, where he volunteered regularly before the pandemic. The organization provides food and supplies to San Francisco residents in need.

With his capstone project completed, Hasegawa has turned his attention to his senior paper on the connections between Jewish secularism and nationalism before the Holocaust. Like Ahad Ha’am and the other thinkers he is writing about, Hasegawa is a dyed-in-the-wool secularist. “I have many concerns about Judaism and God,” he said, lambasting Jewish traditions such as the Passover seder as “more annoying” than meaningful to him at this point in his life.

In the fall, Hasegawa will enroll at Harvey Mudd College in Claremont, which is known for its STEM programs. He plans to study math and physics. As for his puzzle-constructing hobby, he already has several themes in mind that he wants to develop.

“I don’t think this will be the last time a puzzle of mine is published in the New York Times,” he predicted.

Andrew Esensten
Andrew Esensten

Andrew Esensten is the culture editor of J. Previously, he was a staff writer for the English-language edition of Haaretz based in Tel Aviv.