Yale student is a world-class word-bender

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Caleb Madison had his first New York Times crossword puzzle published at age 15. Before coming to Yale, he also created new entries for the Oxford English Dictionary. (Photo by Michael Marsland)

If wordplay were an Olympic sport, rising Yale sophomore Caleb Madison would be packing his bags for London. Indeed, during its coverage of the Olympic games this summer, NBC will profile Madison, whose verbal feats include constructing crossword puzzles for the New York Times and defining new words like “bromance” and “facepalm” for the Oxford English Dictionary (OED).

Crossword puzzles are in the DNA of this New York word prodigy, who grew up in a family where, led by his grandmother, three generations would gather together on Sundays to tackle the Sunday Times magazine puzzle.

What really ignited his passion for playing with words, he recounts, was seeing the movie “Wordplay” when he was in 8th grade. “I was hooked,” he says, after watching the 2006 documentary about the American Crossword Puzzle Tournament (ACPT), a sort of roller derby of competitive crossword solvers, a league that includes former presidential rivals Bob Dole and Bill Clinton.

Madison was so inspired by the movie that he decided to hang out at the next ACPT, hosted by New York Times puzzle editor Will Shortz. The tournament proved to be a watershed for Madison, who managed to convince Shortz — once described as “The Errol Flynn of crosswords” — to offer him an internship at The New York Times.

In 2008, at the age of 15, Madison became not only the youngest crossword puzzle contributor to the Times in Shortz’s tenure, but the youngest in 30 years. Since his debut, Madison has constructed more than two dozen Times puzzles, four of them for the Sunday magazine.

It should be noted that, though Madison was the youngest of Shortz’s protégées to be published in the Times, he was not the first Eli to be mentored by the renowned puzzle-master. Recent Yale graduate Oliver Hill ’12 also arrived at Yale as a freshman with several New York Times puzzles already under his belt. See story.

In another testament to Madison’s word-bending talent, Shortz recommended him as the teacher of a crossword construction class called “Get a Clue,” run by the Jewish Association of Services for the Aged. At the end of the term, the puzzle constructed by teacher and students of “Get a Clue” — familiar to the acronym-loving culture of word players as the “JASA Crossword Class” — is published in The New York Times, an event eagerly anticipated by the publication’s regulars. See the puzzle Madison and his class created.

Puzzle solvers in the crossword blogosphere pronounce Madison a “whiz” and “young phenom,” pointing to such challenging clues as: “It may be combed for hairs” (10 letters, answer at bottom) or the ingenuity of his cryptically themed puzzles. An example of the latter was the puzzle Madison constructed on Woody Allen’s 75th birthday. In the corners of the grid were the director’s first and last name and the two-word title of one of his movies, “Match Point.” Elsewhere in the puzzle, Madison managed to fit in the titles of nine other movies the comedian has made in his long career as a filmmaker.

In the summer between his junior and senior year of high school, Madison added “lexicographer” to his résumé, when he landed an internship at the OED, the self-described “definitive record of the English language.”

As Madison explains it, defining a new word, or more precisely, “proposing a new word as an entry in the OED” is a long, formal process, which begins with a search through at least three databases — seven or more are recommended — for the proposed word, known by OED staff at this stage of its emergence into the language as the “lemma.” The researcher, notes Madison, traces the word to its first recorded use and dates the frequency of citations as the word works its way into the vernacular. In addition to proposing a definition, the researcher also has to provide at least three quotations with the word, including its first known use.

It was his work with the OED that brought Madison to the attention of NBC, which was shooting a short documentary on the history of the definitive English dictionary as part of its coverage of the 2012 Olympics, which kick off in London on July 27. Noting that Madison was one of the youngest contributors to the venerable lexicon, NBC staffer Janelle Gonzalez wrote in an email, ”Caleb was referred to us because of his great personality and friendly demeanor.”

Madison is also known as a quick wit, a talent he hones at Yale as a member of the improv group The Viola Question and the comedy club Just the Tip. Now, having twice tried out his stand-up routine on fellow students, he is testing the waters of major league comedy. This summer he will be serving two internships: at the comedy club Stand-Up New York and on the set of the TV show “Louie.”  Next year, he promises, he will return to the Yale stage doing stand-up with Just the Tip.

Asked what he is seriously considering for a future career, Madison, a likely English major, replies with a playful grin and a shrug: “That’s what I’m at Yale to find out.”

Answer: crime scene

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Dorie Baker: dorie.baker@yale.edu, 203-432-1345