By the time he was 14, David Steinberg had been constructing crossword puzzles for two years. He thought they were pretty good, so he began sending them to New York Times puzzle editor Will Shortz.
Attempts one through 16 received a hard no.
"Then the 17th one came back as a 'maybe,' instead of a 'no,'" Steinberg said. "It was a code-related puzzle, it had kind of a coded message, and he wanted the message to be related to code somehow. I had to rethink the theme a little bit."
Steinberg reworked the puzzle, and it ran in the New York Times the week he finished middle school (Shortz had also published his first puzzle at the age of 14). In 2013, he was the most prolific puzzle constructor at the Times.
Now, newly graduated from Stanford University with a degree in psychology, Steinberg has moved to Kansas City — a major boon to the metro crossword puzzle community.
A month and a half ago, Steinberg took a position as puzzle and games editor at Kansas City publishing house Andrews McMeel Universal, where he’s working on creating new games (though he can’t say what they are).
"I think crossword tournaments are a great way to bring constructors, solvers, and other enthusiasts together," Steinberg said, citing KCUR's two-year-old crossword tournament.
And if anyone can grow the community, it's Steinberg. Even as a teenager he was bringing people together through crosswords.
He had the idea to digitize the Times' crossword archives — the Pre-Shortzian Puzzle Project.
"I had always been curious about the old Times crosswords," Steinberg said. "I knew the Times crosswords had started in February of 1942, but the only ones I could see online were from the Shortz-era, from November 1993 to present."
At the height of the project, and while he was still in high school, he managed a team of 60 volunteers. He met Bernice Gordon through the project and Shortz when Steinberg was 16 and she was 99. Until her death in 2015, she reigned as the oldest Times puzzle contributor.
Steinberg traveled to her home in Pennsylvania and they constructed a puzzle together. He discovered that Gordon still liked to use the traditional crossword books. He preferred to use websites to find words with just the right number of letters, or pattern of letters for his clues.
However the words are nailed down, he said, making the grid is the hardest part. He starts with a theme for most puzzles. Once he has that, he makes three to five symmetrical theme entries, which he lays out on the grid. Then he places the black squares.
"I'd say the biggest challenge is filling in the rest of the answer words," he said. The one he constructed with Gordon was age-themed. "The revealer across the center was 'age difference,'" Steinberg said. "So, half the theme entries added -age to a common phrase and half of them removed -age."
He was in deep with crosswords. But, he wondered if he could study crosswords and support himself with that work. That seemed unlikely, so he tried computer science; it wasn’t as much fun as he thought it would be.
Each time Steinberg consciously searched for his "passion," he again found crossword puzzles.
For a couple of summers during college, Shortz hired him to sort through Times puzzle submissions; he spent one of those summers sleeping on Shortz's couch.
Constructing puzzles gives Steinberg a satisfaction that nothing else does. Mainly that's in coming up with a really good theme or a clue that no one’s done before.
Just recently, here in Kansas City, he had one he was pleased with.
The clue was: One concerned with inequalities in education?
"The question mark indicates that some sort of word play trickery is going on," Steinberg said.
The answer was "math teacher."
David Steinberg spoke with KCUR on a recent edition of Central Standard. Listen to the conversation here.