![]() Today, almost all constructors use software to make crossword puzzles. I think the person who hired me saw the coming changes in publishing and that it would be helpful to have someone who was a little computer-savvy and could adapt to the digital world. I was the youngest crossword editor in the Times’ history. I think I was hired partly because of my youth. I was thirty-six years younger than Maleska. ![]() Maleska, passed away in 1993, and they were looking for a new editor. Unlikely bedfellows! You took over as crossword editor at the Times in 1993. That’s how I made my first professional-quality crosswords. My junior year, I found a professor in the English department who liked crosswords and was willing to work with me, so every couple of weeks I took a crossword that I had made into his office as he sat and solved it and critiqued it. ![]() I assume a lot of your studies were about the history of puzzles and making puzzles? You went to Indiana University, where you designed your own major in enigmatology. And not surprisingly, puzzle-maker was not there. I remember adding up my figures, turning the page, and looking to see puzzle-maker on that list of professions. I remember a questionnaire I took in grade school where you would fill out all the things you like and don’t like, and then find what profession you’re best suited for. In the eighth grade, when asked to write a paper on what I wanted to do with my life, I wrote on becoming a professional puzzle-maker. I sold my first one, when I was fourteen, to my national Sunday-school magazine. I started making puzzles when I was eight or nine. When did you first get into puzzles? Do you have an earliest memory of solving a puzzle? It had the word “dove” twice, one of them clued as the bird and one as the past tense of “dive,” so that’s how they dodged that accident. The first word across was “fun,” that was filled in for you. It’s the Fun section of the New York World from December 21, 1913. I have what I believe is the world’s only copy of the first crossword puzzle in private hands. Are there any collector’s items you can tell me about? I’ve heard that you have a whole collection of puzzle-related ephemera up there. We’re talking over Zoom, and you’re in your home, in Westchester. Afterward, he sent me a few of his favorite crossword clues, which you can attempt to solve below. In our conversation, which has been edited and condensed, we talked about some non-puzzle things, too: his love of table tennis, his cameo on “The Simpsons,” and the surprise of finding his first serious romance, late in life. Navigating these changes seems to have done nothing to dampen Shortz’s enthusiasm for the job the man was clearly put on this earth to puzzle. He now shares his duties with a team of associate editors, and he happily acknowledges that their array of backgrounds and habitus has made for a better crossword. To a rising generation of crossword enthusiasts, he is at once a revered maestro and a frustrating embodiment of the Old Guard.Īlthough he resists crossword-clue relativism, and maintains that some references are simply more significant than others, Shortz has changed with the times in certain ways. But he is a self-described “older white guy,” and his judgments have drawn criticism, at times, for catering narrowly to his demographic. Part of his job, as he sees it, is to adjudicate what any puzzler should know. ![]() Now, at the age of seventy, and approaching his thirtieth anniversary at the paper, he is a member of the established cohort he once defined himself against. He published more contributors in their twenties and thirties, and favored clues with a modern sensibility: Greek prefixes and musty arcana were largely swept away, replaced by sitcoms, snack-food brands, and sprightly wordplay. ![]() When Will Shortz took over as the crossword editor at the Times, in 1993, he set out to make the puzzle younger. ![]()
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