Puzzle Master

Sam Ezersky (Engr ’17) remembers being 5 or 6 years old and sitting in a Hair Cuttery, bored, waiting for family members to get their haircuts. He picked up a magazine and started flipping through, and inside found a Fill-It-In, a kind of puzzle that gives the reader a word bank to complete a grid. Ezersky was fascinated. He remembers another day soon after: His mom pulled him around their neighborhood in Northern Virginia in a little wagon, encouraging him to look around, take it all in. Instead, he was immersed in a book of puzzles. It wasn’t about finishing all the puzzles, he says, “I was more interested in how [the puzzles] worked.”

Not all puzzles were the same. As a 12-year-old, Ezersky watched his stepfather complete crosswords in the Washington Post. “At first I didn’t like crosswords,” Ezersky says, “because you actually had to know stuff. And I felt like I didn’t know anything.”

But a turning point came when he was 15, and his mother got him a book of New York Times puzzlemaster Will Shortz’s (Law ’77) best crosswords. “They blew the other crosswords out of the water,” Ezersky says. “I wanted to be one of those people one day, creating things like that.”

It was in March of 2012 when Ezersky, then 17, had his first crossword published in the Los Angeles Times. “My first puzzle being accepted was just insane to me,” he says. “I’d never really told too many people about my hobby.” But once he got the news, “I outed myself.” On July 28, 2012, in collaboration with puzzle creator Victor Fleming, he had his first puzzle published in the New York Times, becoming the sixteenth-youngest crossword publisher since the paper began keeping track in 1942.

Will Shortz receives 75 to 100 crossword submissions a week. “Competition is stiff,” Shortz says. “I look for something that is fresh, interesting and consistently done.”

When it comes to Ezersky’s puzzles, Shortz starts listing answers that impressed him:

• ‘Makes a mess’ [clue: Is guilty of disorderly conduct?] “That’s a fresh answer; it probably has never appeared in a puzzle.”
• ‘Boy soprano’ [clue: Kid getting into treble]
• ‘Alaskan King Crab,’ [One with long, luscious legs]
• ‘PC help.’ [clue: Geek squad service]

“It’s very hard to find fresh vocabulary in answers of six or fewer letters because there’s not much that hasn’t already been done,” adds Shortz.

Like with any skill, crossword creation takes trial, error and many hours spent alone. “I think of a sort of theme that I can execute,” says Ezersky. “I try to make it the most novel idea I can think of, something that will really excite Will. Then I go about designing a grid. I put the longer theme answers first, and then black squares around them, going for the best fill possible. I’ve always got something I could be working on; the gears are always turning.” However, it doesn’t take precedence over academics, he says. “It’s a distraction, but it doesn’t hinder my performance. If anything it enriches my vocabulary.”

But puzzle creation is not a completely solitary endeavor. Both Ezersky and Shortz, who met for the first time at a tournament, talk about the community, the people they meet along the way, as being one of their favorite aspects of the craft. “With crosswords what you have is a common way of thinking,” says Shortz. “The people tend to be well rounded, with flexible minds and good senses of humor, where you can talk about anything.”

“It’s a huge part of me,” says Ezersky, who plans to double major in mechanical engineering and economics, and who volunteers through UVA’s Madison House, helping kids at a local elementary school read and complete their homework. “Crosswords aren’t my life, but it’s a huge passion for me.” 

So far, he’s had five puzzles in the New York Times, and he’s still going strong. The most satisfying part of the process? Finishing. “I love test solving, or sending a puzzle to one of my colleagues. It’s looking back on the process and thinking, ‘It’s taken me this many days, and I finally got it.’”