He’s Got a Clue: Teenage Crossword Whiz

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Usually, the old impart knowledge to the young. But every Sunday at John Jay College, 17-year-old Caleb Madison teaches the art of crossword puzzles to people three and four times his age.

“I’d say the age range is from 55 to 75,” Madison said. “A 40-year-old tried to come in the classroom once and we chased him out with our canes. We don’t tolerate those kinds of hoodlums.”

Madison was recommended to the “Sundays at JASA” program, which offers the class, by famed New York Times crossword puzzle editor Will Shortz. The Jewish Association of Services for the Aged, which coordinates the program, pays Madison $50 a class, called, “Get a Clue!”

High school junior Caleb Madison leads a class in crossword construction. Photo by Andrew Schwartz

Madison, an Upper West Sider and junior at Bard High School Early College, became interested in crossword puzzles after watching the 2006 documentary Wordplay, which focused on Shortz’s career. Intrigued, Madison decided to attend the American Crossword Puzzle Tournament, held annually at the Brooklyn Bridge Marriott. He met Shortz and inquired about an internship. Starting in the summer of 2007, Madison worked with Shortz for a year, learning the basics of crossword construction.

“Will Shortz is the hardest working man in puzzle-business,” Madison said. “He receives thousands of submissions each week, and not only reads, but responds to them all. Additionally, he has to edit, fact-check and typeset six regular and one Sunday puzzle a week, plus a second Sunday Magazine puzzle. I basically helped him keep up on correspondence, fact-check and edit clues, typeset grids and, occasionally, plan for tournaments.”

In May 2008, when he was just 15, Madison became the youngest person to have a crossword published in the Times since 1976. Since then, Madison has had nine more crosswords published in the paper, and the Times ran a crossword that was a joint production of Madison and his JASA class Feb. 18.

“The most difficult thing is getting adults from the mentality of solving puzzles to one of constructing puzzles,” said Madison. “It’s hard for some people to comprehend that someone did make this particular puzzle, that this puzzle is in itself a creative enterprise.”

Madison starts each semester-long unit by demonstrating the basics of putting together a crossword puzzle before moving on to constructing more complex puzzles and themes.

“A word theme is three or more answers that tie the puzzle together,” Madison said. “The class works toward more elegant themes because that’s what the New York Times will accept.”

The theme of the Feb. 18 puzzle was “Commercial Breaks.”

“We used four movies, each of which had the word ‘ad’ inserted in the title to make it something different,” Madison said. “For example, we had ‘Best in Shadow,’ instead of Best in Show and ‘Addressed to Kill’ instead of Dressed to Kill.”

The class, first introduced in October 2009, runs through May 23 and is still accepting new students. For more information, contact Sara Tornay at 212-273-5304 or stornay@jasa.org.

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