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The crossword wizard is at a crossroads.

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David Steinberg

David Steinberg has had 101 crosswords published in the New York Times, making him the most prolific crossword constructor, age 25 years or younger, the vaunted publication has ever had. He’s the subject of this week’s cover story.

Christopher Neely here, wondering how quickly you can complete a crossword puzzle. 

If you asked me a few months ago, I would have said probably a week, or a weekend if I was feeling extra brainy. Today, I can confidently say a day, sometimes a few hours if it’s an easy puzzle. The change in my ability isn’t the product of some Matrix-esque upload of textbooks and dictionaries to my brain. Well, not exactly. 

It’s that, for the last two months, I’ve been spending time with David Steinberg, the 25-year-old, Pacific Grove resident who clocks anywhere between 3 and 10 minutes to complete any crossword, which he usually accomplishes with a pen and zero mistakes. 

Steinberg is, by all accounts, a prodigy in the world of crosswords, though his specialty is more construction than solving. Longtime and legendary New York Times crossword editor Will Shortz published Steinberg’s first Times crossword when he was only 14 years old—a record at the time. It was the 17th crossword Steinberg had sent to Shortz. Today, Steinberg has had 101 crosswords published by the Times, which Shortz tells me makes him, “far and away the most prolific crossword constructor [25 years or younger] the New York Times has ever had.” 

Steinberg, who is the subject of the cover story in this week’s print edition of the Weekly, was 12 years old when he submitted his very first crossword to the Times. Since then, he has competed in and won at the American Crossword Puzzle Tournament, secured a job at 15 years old editing the daily crossword for the Orange County Register, published a book of his original crosswords, and started a global effort to digitize all 16,200 crossword puzzles published in the New York Times before the Shortz era began in 1993. Steinberg used crosswords to help him gain admission to Harvard, Yale, Princeton, Pomona, and his eventual choice, Stanford. He was also invited in consecutive summers to join Shortz at his New York home for internships in crossword editing—summers which taught Steinberg a lot, including that Shortz’s favorite cereal is Alpha-Bits. (Although, Shortz tells me that, at some point, Post changed the recipe, thus killing his Alpha-Bits flame.)

Today, Steinberg occupies an esteemed position in the crossword world. He is editor of the Andrews McMeel Universal crossword puzzle, which publishes daily in vaunted publications such as the Philadelphia Inquirer, Dallas Morning News, Miami Herald, San Francisco Examiner and Boston Globe. Puzzles offer a narrow career path, but Steinberg, at only 25, has earned a seat among the rare few—you can likely count them on one hand—who earn a comfortable living deciding which crosswords millions of American solvers see everyday. 

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Although he wields an inhuman ability with word-themed puzzles, Steinberg is undoubtedly human, and crosswords have dominated more than half of this young human’s life. 

As we spent more time together over the last two months and pushed beyond the flashiness of his crosswording skills, Steinberg began to open up. He feels lucky to be doing what he loves, but he acknowledges crosswords have consumed his life, at the sacrifice, he now realizes, of much else. We talked about his lament over missing out on experiences as a kid and young adult because of crosswords. We talked about issues he has had finding a social life, his struggles in the dating world, and the alienation he felt during his school years when he realized he was the only person his age interested in crosswords. 

The last two years have forced the young crossword genius to rethink his path. Steinberg admits he is frustrated, though, as with many of us, he is unsure where pandemic frustration ends and life frustration begins. The crossword wizard is at a crossroads. 

For more on that, you’ll have to read the story—on newsstands now. As always, write back with your feedback, and please let me know how quickly you are able to complete the original crossword puzzle Steinberg provided for the piece (newsstand version only). I’m dying to know your times. Oh, and here’s a helpful tip I learned from the crossword wizard that revolutionized my game: instead of going in linear order by clues, try to tackle one section of the grid at a time.

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Christopher Neely covers a mixed beat that includes the environment, water politics, and Monterey County's Board of Supervisors. He began at the Weekly in 2021 after five years on the City Hall beat in Austin, TX.

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