How a Crossword Puzzle Pro Landed His Dream Job

Sam Ezersky, associate puzzles editor for the New York Times, says his passion began at an early age.

Sam Ezersky pauses on the Hoboken waterfront to revisit the Super Mega puzzle he constructed for the December 15 edition of the New York TimesPhoto by Matt Furman

Sam Ezersky was six years old, thumbing through a magazine, when he came across a simple word puzzle. Captivated by the way the words came together, he sought out more puzzles. His mother and stepfather encouraged his interest. Soon he was peeking over their shoulders, contributing answers as they worked on their own puzzles.

A crossword-puzzle book by Will Shortz, the longtime crossword editor of the New York Times, fueled his fascination. He viewed the puzzles not just as a solver, but as a potential constructor. “This was the turning point,” says Ezersky, now 24 and a resident of Jersey City. “I thought I would love to have a puzzle published by the New York Times.”

At 14, Ezersky started sending puzzles to Shortz, who rejected a bunch, but encouraged him to keep trying. And Ezersky did. At 16, he sold his first puzzle to the Los Angeles Times and at 17, in collaboration with another puzzler, he sold a puzzle to Shortz. “It was the greatest state of euphoria that I’d ever felt,” says Ezersky.

A few years later, during Ezersky’s third year at the University of Virginia, his idol, Shortz, was giving the keynote speech to graduates. “I reached out to him,” says Ezersky. “We got together and chatted about puzzles for hours.” 

The following year, Ezersky spent his winter break as an intern for Shortz and, after graduation, started working as associate puzzle editor for the Times. “This is my dream job, my passion,” says Ezersky. “When I submitted my first puzzle to the Times, I never thought that I could make a career out of it.”

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Ezersky, Shortz and a third editor, Joel Fagliano, read every one of the approximately 600 monthly puzzle submissions and offer personalized feedback. “We reject ones with answers that are too obscure or themes that aren’t interesting,” says Ezersky. “The goal is to give the solver a sense of accomplishment and enjoyment.” 

In preparing a puzzle for publication, the editors alter about 50 percent of the clues, rarely changing the words in the grid, and match the puzzle’s difficulty to the day of the week, Monday being the easiest and Saturday the most difficult. Sunday is not the hardest, just the largest. 

Ezersky still occasionally submits his own puzzles to the Times; one was published in the Sunday, February 16, magazine section. When he constructs a puzzle, he devises a theme with answers that form the backbone of the grid. Then he drops in the black squares and fills in the words for the rest of the grid. The clues come last.  

Ezersky solves puzzles from other publications whenever he finds the time. For several years, he competed at the American Crossword Puzzle Tournament, a speed-solving competition in Stamford, Connecticut. In 2016, he finished first in the under-25 group, and 28th overall.

When he’s not working with puzzles, Ezersky enjoys spending time in neighboring Hoboken walking along the waterfront and watching sports in the bars filled with young people—like the ones crossword puzzles are starting to attract.

“These days, crosswords are less of a nerdy hobby,” says Ezersky. “We’re catering to a bigger and more diverse audience who can solve digitally in an app or on a computer, as well as on paper.”  

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