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Teenage Crossword Puzzle Maven Goes Digital

How a 17-year-old New York Times-published puzzler is changing the game

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It may surprise you to learn that this Saturday’s New York Times crossword puzzle—the most difficult puzzle of the week and a wicked mental undertaking—was built by a 17-year-old who lives with his parents in the Los Angeles suburb of Rancho Palos Verdes. But David Steinberg, a friendly, articulate high school junior, is in fact a crossword puzzle veteran, having had his first puzzle published by the Times when he was 14—making him the second-youngest person to enjoy such an honor.

The New York Times crossword, edited by Will Shortz, is popularly regarded as the crème de la crème of mainstream puzzles. And while solvers toil through Steinberg’s Saturday grid over a cup (or three) of coffee, the teenager will be in Brooklyn at the 37th American Crossword Puzzle Tournament, or ACPT, speaking about his newest brainchild: a collaborative online database of New York Times crossword puzzles published between 1942 and 1993, when Shortz began as editor (puzzles published since then are already available online). Steinberg calls it the Pre-Shortzian Puzzle Project.

At 12, Steinberg was inspired to try his hand at constructing puzzles after watching Wordplay, a documentary about the world of crossword puzzles that features the ACPT and Merl Reagle, a godfather cruciverbalist who builds puzzles by hand. “He made the process look very easy,” Steinberg said. “I went and I got out a piece of graph paper and tried constructing my first crossword puzzle.”

Steinberg submitted it to Shortz at the Times but the puzzle was promptly rejected. Still, Shortz encouraged Steinberg to keep trying while providing the young teen with feedback. By submission 17, Steinberg had hooked the crossword editor. The puzzle, which required solvers to crack a code in the middle entry, was published on Thursday, June 16, 2011. “That was super exciting for me,” Steinberg said of becoming the second-youngest Times-published crossword constructor under Shortz’s editorship.

Since then Steinberg has published a total of 25 puzzles in the New York Times, including 15 in 2013, the most of any constructor last year. He’s also been published 12 times by the Los Angeles Times, as well as in various other outlets, including Newsday, which is edited by Stan Newman. (Newman and Shortz are the editorial advisors on the Pre-Shortzian Puzzle Project.)

Steinberg estimates that he’s published 95 puzzles in all, not including the 25 he published in a book of his own. “I kind of lost count after a while,” Steinberg said. “There are so many different markets.”

In October 2012, the Orange County Register wrote an article about Steinberg and surprised him a few weeks later with a job offer: a crossword puzzle editorship. “It was completely unexpected,” he said. “Now that was really exciting.”

He gladly accepted the position, adding another superlative to his résumé: youngest-ever crossword editor, at 15 years old.

By the time Steinberg published his first puzzle in the summer of 2011, he’d switched from building them on paper to using computer software. “I originally decided to construct by hand because I thought that computer software was kind of cheating, and maybe it produced inferior results,” Steinberg said. “I soon discovered that I was wrong and that computer software was the industry standard.”

Now, Steinberg has gone all-in with computers. The Pre-Shortzian puzzle project began as part of a ninth-grade science research project, when Steinberg began plugging in, letter by letter, New York Times crossword puzzles published before the Shortz era, converting them into an analyzable, digital format. But to finish the job alone—50 years of puzzles—would be monumentally time consuming. So he opened up the project to the crossword community, a fervent, opinionated, and brainy bunch. So far 40 people, called “litzers” after the crossword software maker Lit Soft, which produces Across Lite, an industry standard, have volunteered their time, along with a group of proofreaders. Once a puzzle is converted, the information is uploaded onto xwordinfo.com, a crossword database.

Steinberg says that the litzers are almost done converting Pre-Shortzian puzzles from 1993 through 1949, and just under seven years of puzzles remain. And because the New York Times published only one puzzle per week until 1950, the project’s completion is likely imminent (as of today the website lists that 15463 out of 16225 puzzles have been “litzed”).

Steinberg will present an update on the Pre-Shortzian Puzzle Project this Saturday at the ACPT, along with research about the intersection of gender and crosswords. He was recently awarded a $25,000 Davidson Fellows Scholarship in the “Outside the Box” category—pun unintended—which goes towards college tuition.

Picking a major, however, may be Steinberg’s biggest challenge yet. “Of course if there was a crossword puzzle major, I’d be pursuing that,” Steinberg said. “There are so many other wonderful fields out there. I particularly like computer science because it involves a lot of puzzle-related fields, and also I’m interested in the Classics—Latin and Greek—that kind of thing. It connects with puzzles in a different way.”

Jonathan Zalman constructs a monthly crossword puzzle for The New Inquiry. Follow him on Twitter @ZalmanJ

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Teenage Crossword Puzzle Maven Goes Digital

How a 17-year-old New York Times-published puzzler is changing the game

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