If bar trivia and reading had a child together, the result might be a crossword puzzle. Combining the competitive thrill of getting the right answer with the armchaired pleasure of wordplay, crossword puzzles are, for many of us, a cherished daily routine. And for a small number of very clever wordsmiths, they are a calling.

Jeff Chen, a Bay Area native who’s lived in Seattle for about 25 years (he moved here for a relationship that didn’t work out “but Seattle worked out,” he said), is a master crossword constructor. He’s had more than 125 puzzles published in The New York Times — the gold standard of crosswords — as well as many more in the Los Angeles Times, The Wall Street Journal and others. Chen’s most recent NYT puzzle is a monumental one: the annual Super Mega, a 50-by-50-square monster that was part of the paper’s yearly Puzzle Mania section in December.

“There are very few people who can create a crossword this good, and he’s one,” said New York Times puzzle editor Will Shortz, in a phone interview last month, of Chen’s Super Mega effort. He praised Chen’s ability to produce “first-class puzzles” and noted his high standards for words and clues: “He does not like substandard fill at all — uninteresting obscurities and crosswordese, those short answers with lots of vowels that appear often in crosswords. He wants as many answers as possible to be positive, to be really interesting, colorful, juicy vocabulary. He really works his grids to make them as lively as possible.”

You’d think that Chen, whose background is in mechanical engineering and technology (he co-founded the pharmaceutical company Acucela, which went public on the Tokyo Stock Exchange in 2014), would be a lifelong crossword fan, but he isn’t. He only began solving puzzles back in the early 2000s, when he first met his wife, Jill Denny.

“I just started out of curiosity,” he said. “She’s a really good solver. We would have dates on Sundays where both of us would have a copy of the Sunday New York Times crossword in parallel. She could be done in 20, 25 minutes and she would patiently sit there drinking her coffee, nibbling on something, while an hour or two or three hours would pass. Since then I’ve improved quite a bit. But I’m still certainly not one of the top-speed solvers.”

He was inspired to take the step from solving to constructing after seeing the documentary “Word Play,” which features Shortz and many crossword constructors including the late Merl Reagle, whose lively puzzles ran in The Seattle Times on Sundays for many years. “I thought, I want to take a shot at it and see how hard it was,” Chen remembered. “As it turned out, it’s very easy to make a terrible puzzle.”

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But he loved the challenge of it — finding that balance of a technically sound puzzle with artistic elements — so to work he went, only to find his early submissions to the NYT politely rejected. Shortz’s trademark rejection phrase, Chen said, is “the theme didn’t excite me” (translation, according to Chen: “This is boring as hell”). But he kept trying — more than 20 times, he said, over about two years — and noted that he was starting to get more encouragement from Shortz’s rejections, phrases like, “This is getting closer.”

Finally, Denny suggested a theme — playing on the names of body parts — and the two of them fleshed it out together. It was accepted and ran in the paper on Monday, July 5, 2010. (Fun fact: The answer to clue 6 across, “___ of the D’Urbervilles,” is the name of Chen and Denny’s daughter, who arrived several years after the puzzle’s birth.) Shortz said that it’s not at all uncommon to have multiple rejections — “Some people submit for years before getting an acceptance” — and that these days, he’s getting more than 200 submissions per week for the seven puzzle slots. 

Since then, Chen’s immersed himself in the world of crosswords. He creates about five puzzles per month: a simple weekday puzzle might take five or six hours, a Sunday puzzle (NYT puzzles get more complex as the week goes on, with the Sunday one being of moderate difficulty but much larger) maybe five to 10, but possibly as many as 50. The Super Mega puzzle, the largest one he’s done, was weeks of effort. “It nearly killed me,” he said, laughing.

All start with a theme, some clever bit of wordplay that allows for multiple clues and answers, and that might be reflected in the grid’s creative shape. “Everything has to be built around your theme entries,” he said, “so it’s important to spend enough time making sure that the theme is interesting, fun, entertaining, amusing — some sort of combination of elements that produces an ‘aha’ moment.” For example, one Chen puzzle from 2011 had an elegant yin yang grid design; another from 2016, featured “storms” of letters forming words in circles. Though he uses a couple of different crossword software programs, “there’s still a tremendous amount of manual work that goes into layout and fill.”

The NYT has an elaborate list of requirements for crosswords; constructors must ensure that their grids are symmetrical, that there are no words shorter than three letters, and that their clues are clever, witty, and reflect a diversity of cultural references. The paper’s crossword culture has changed significantly since Shortz began his position in 1993; previous crossword editor Eugene Maleska, Chen said, “took pride in making things obscure.” That’s what Shortz means when he says “crosswordese”; Maleska, Chen said, was famous for allowing the word OREO, but only with the clue “Mountain: Comb. form.” In Shortz’s era, he’s worked to eliminate that kind of obscurity, making the puzzles more playful and bringing more pop culture into the mix.

Chen is unusual among crossword constructors in that the majority of his NYT puzzles are done in collaboration. As the longtime editor of the website xwordinfo.com, a resource for aficionados of the NYT crosswords, he’s frequently approached by new constructors asking for advice — and frequently ends up jointly creating a puzzle with them.

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“These days, 90% of all my work is with other people,” Chen said. “I just find it fun to try to help other people achieve their dreams. As long as people are polite and they’re willing to listen to feedback, I’m happy to work with just about anybody.”

Christina Iverson, who lives in Ames, Iowa, is one of those people who wrote to Chen for advice and ended up collaborating; they’ve now created six puzzles together, though they’ve never actually met in person. “I think he’s really good at helping new constructors hone their ideas and elevate their themes to the next level,” she said. “He’s really generous with his time and with his resources … And I think he feels that new constructors have new interesting ideas and he wants to help them bring those ideas to the world.” Now a NYT-published crossword constructor on her own (she created the Sunday, Dec. 26 puzzle), she’s now mentoring new constructors herself. “I was very much inspired by him.”

Chen, who has a new book of puzzles coming out in the next few months from Rockridge Press (he’s also the author of two books of bridge-inspired crosswords and two middle-school novels), said that he’s seen a “huge increase” in traffic to his website since the pandemic began, as well as in the number of people contacting him. “They’re just looking for something to do,” he said, noting that he tries to reply to as many requests as he can. “If I can help somebody pass the time a little more pleasantly during this time, I’m happy to do so.”