“I didn’t think it was possible to have a career in puzzles,” he recalls. His plan was to work as a lawyer for 10 years and make enough money to then focus on his love of puzzles and games. Not surprisingly, he killed the LSAT, especially the logic games section. “I approached it as a puzzle. I loved taking tests.”
Shortz was accepted to law school at the University of Virginia, in part, he believes, because of his unusual undergraduate background. “I think they liked my ingenuity and resourcefulness.”
But in the spring of his first year, he wrote his parents a letter, telling them he’d be dropping out at the end of the year. There was, Shortz quips, a “little longer pause than usual between my parents’ letters.” Eventually, his mom wrote back, suggesting that dropping out of law school was a terrible idea. “She wrote, ‘It’s your decision, and we’ll love you whatever you decide, but we recommend you get your degree and then do whatever you want,’” he says. “I realized she was right. Law school was good training and useful. Plus, it’s not a good thing to quit anything. So I continued.”
At that point, Shortz “felt released” and no longer felt compelled to study traditional law subjects because he didn’t plan to take a bar exam. Instead, he took courses in intellectual property and copyright protection, gaining knowledge he planned to apply to his puzzle career.
After graduating law school in 1977, Shortz joined Penny Press, a newsstand puzzle company he’d worked for in college. “In my third year of law school, I was the only student not interviewing for a traditional job. The career services office called me in and asked about my plans for the next year. When I said I was joining ‘Penny Press,’ they waited for the rest of the law firm name,” Shortz remembers with a laugh.
Before long, he became an editor at Penny Press and later moved to the New York Times, where he took the helm as the crosswords editor. Today, he works for the Times from his home in Pleasantville, New York, and broadcasts puzzle segments on National Public Radio. He’s authored dozens of puzzle books.
Although Shortz never took the bar or practiced law, he says he doesn’t regret going to law school. As his career has transitioned to a freelance basis, he draws on his legal knowledge for his business. Also, he says, law school enhanced his puzzle career, especially when phrases like “res ipsa loquitur” appear as crossword puzzle clues.
“Law school is terrific training for the mind,” Shortz says. “It teaches you how to approach a complex issue and break it up into parts. Law school made me a better puzzle solver.”