From his daily crossword puzzles in The New York Times to his appearance on the Simpsons, it’s hard to picture a puzzle-making company rejecting Will Shortz for a summer internship given his cultural ubiquity today. But that’s exactly what happened, he told the crowd in Marshall Auditorium on Feb. 10, during a talk that was part of the annual Speaker’s Committee series. After applying to several firms, only one offered him an internship, thus setting off a chain of events.
By the time he was a law student at the University of Virginia, Shortz managed to collect enough courage to inform his parents that he was going to drop out—though he buried the lede in the middle of a lengthy letter. His parents, however, managed to convince him to graduate law school, though he never took the bar exam. Instead of utilizing his law degree, he went straight into pursuing his passion of puzzle making.
“I always wanted to have a career in puzzles, but I didn’t think there was any money there,” he told the audience. “I thought I’d just be the creepy old guy living in my mother’s attic selling my puzzles for $10 a pop.”
Shortz began his talk, however, by noting that the audience had another puzzle master in their midst. Swarthmore senior Anna Shechtman, who was present Friday night, recently sold one of her puzzles to The New York Times. Shortz explained that what made Shechtman’s puzzle so unique from the 75 to 80 puzzles he receives daily was that it used Greek letters to help spell out the longest answer: “it’s all Greek to me.”
According to Shortz, a great crossword puzzle consists of a mixture of creativity and aesthetics. He noted that a visually unappealing puzzle can really discourage the reader. Some common puzzle-making mistakes are simpler, however.
“Here’s a rule you would think would be obvious for anyone creating a crossword puzzle for a newspaper, but I can’t tell you how many submissions I get that break this rule,” Shortz said. “Every answer has to be a real word or phrase. You can’t just make stuff up.”
To cap his talk, Shortz divided up the audience into the “Black Squirrels” and the “Grey Squirrels” for a puzzle contest which included a number of different games. Some games utilized wordplay (puns, rhymes, etc.) while others were more trivia-based. Thanks to an impressive fifty-five point answer streak by Joe Horowitz ’14, the Grey Squirrels soundly defeated the Black Squirrels, 75 to 25.