2009 Winner Takes Home First Place in 21st Westchester Crossword Puzzle Tournament

man in front of a crossword puzzle
Jeffrey Schwartz, winner of the 21st Westchester Crossword Puzzle Tournament, standing in front of his winning board. Schwartz last won the tournament in 2009. (Pleasantville Press/Kamari Stewart)

Three rows of tables filled up the front half of the room in Westchester Table Tennis Center. Bowls of pretzel rods sat on each table, along with a piece of paper flipped over, and a pencil at its left.

Fifteen minutes sat on the clock.

“You may begin…now,” a voice said into the microphone.

The sound of flipping pages filled the room and all that could be heard was graphite furiously scratching away.

The 21st Westchester Crossword Puzzle Tournament hosted by Will Shortz, owner of the Westchester Table Tennis Club and Crossword Editor for the New York Times, was held on Friday, Oct. 19.

Will Shortz always knew that he wanted to “have a career in puzzles,” he said. He holds the world’s only college degree in puzzles — a degree in Enigmatology from Indiana University. Shortz has been the crossword editor for the New York Times for 25 years.

A hand shot into the air. There was still 12:18 left on the clock. A referee came around to collect their paper and note the time remaining. Within 20 seconds, more hands were in the sky.

Once the timer went off, Shortz announced that there would be a short break before the next round. The room erupted like a classroom after the SAT.

Will Shortz is the head and host of the Westchester Crossword Puzzle Tournament. Shortz has been the crossword editor for the New York Times for 25 years. (Pleasantville Press/Kamari Stewart)

Many of the contestants at this year’s tournament are friends who travel together and compete in crossword tournaments in the area, according to Elizabeth Brody, the chair for the tournament and board member for the Pleasantville Fund for Learning (PFFL). This year, only seven contestants were Pleasantville locals, including the mayor’s daughter and winner of the “Local” trophy, Caroline Scherer.

The Pleasantville Fund for Learning is a non-profit organization that provides grants to teachers for things that aren’t covered in their initial budget.

The tournament has served as a fundraiser for the PFFL almost every year since its inception, according to Shortz. While the turnout varies from year to year — this year hosting about 45 contestants and raising over $1000 — Brody said the tournament is “more nostalgic than moneymaking.”

With three rounds, the finalists of each round would go on to compete in the “playoff round” where they were tasked with completing a crossword on a whiteboard at the front of the room for all to see. This year’s finalists were Jeffrey Schwartz, a 2009 winner; Glen Ryan, a 2005 winner; and Nancy Taubenslag.

With all on eyes on them and a mere 29-second difference between first and second place, Jeffrey Schwartz was declared the winner of the 21st Westchester Crossword Puzzle Tournament after completing a perfect puzzle in two minutes and six seconds.

Schwartz, an Assistant Professor of Engineering Technology at Queensborough Community College, has been competing in the Westchester Crossword Puzzle Tournament since around 2003.

“I never thought I’d win again after 2009,” Schwartz said, beaming with pride.