America knows your work as the crossword puzzle editor of The New York Times and “puzzle master” on National Public Radio’s Weekend Edition Sunday. Less well known is the fact that you have deep roots in Indiana.
I was born and raised in Crawfordsville in Montgomery County. I grew up on a 50-acre Arabian horse farm on the edge of town. So despite having lived most of my life in the East, I consider myself half-Hoosier. By the way, I’ve committed to donating the farm where I grew up to the city of Crawfordsville for a nature park. It will have miles of trails over hills and through woods, as well as a permanent puzzle treasure hunt that visitors of any age can play. That’s a good indication of my emotional attachment to Indiana and my sense of indebtedness to the place where I came from.
What are your fondest memories of your childhood?
Oh, lots of things. Riding ponies in the woods with my best friend, Pat; competing in the annual 4-H horse and pony show; reading about the history of puzzles in periodicals at the Wabash College Library; playing on the Crawfordsville High School tennis team—I was number 2 during my senior year; and competing on the high school debate team. My debate partner, Jack Oest, and I won many trophies in tournaments around Indiana.
Was your mom or dad into word play or solving puzzles at all?
No, I was the only puzzle person in the family. However, I was fortunate in having a mother who was a writer. She was always submitting stories for publication. Once she saw my interest in creating puzzles, she showed me how to submit them for publication.
Do you remember the first puzzle you ever did? My guess is that it was in The Indianapolis Star.
My family subscribed to the Chicago Tribune, actually, which carried Jumble, a scrambled-word game, daily. That was my favorite. Eventually, I was able to complete Jumble on most days in 10 or 15 seconds.
When did you first sell one of your own puzzles?
I sold my first one to Venture, my national Sunday school magazine, when I was 14. At 16, I became a regular contributor to Dell puzzle magazines. My first book of puzzles was published when I was 27. Today I’m the author or editor of more than 750 books of crosswords, sudoku, or other puzzles.
Besides having good vocabularies, crossword puzzle experts need broad knowledge of history and current events. Did that affect your choice of major at Indiana University?
When I went off to Bloomington, I first intended to major in history, mostly because I love it. Then I switched to economics because I enjoyed a first-year honors course on the subject. During my sophomore year, though, my mom read about an innovative new program at IU called the Individualized Major Program. If you were accepted, you’d be able to major in literally anything. I had always joked about majoring in puzzles at college, never imagining that it was possible. But I was accepted into the program, and by my senior year, I had officially changed my major to enigmatology, the study of puzzles.
How did that work, forging ahead with a major that didn’t exist?
I took independent learning courses. But as IU had none on the subject, I made them all up myself! I found professors who’d work one-on-one with me on the subjects I was interested in. For example, I took a course on crossword construction with the help of an English professor who liked puzzles. Every few weeks I’d go into his office with a new puzzle I’d made, and I sat by his side while he solved and critiqued it. Other courses I came up with were on mathematical puzzles, logic puzzles, anagrams, crossword magazines, and the psychology of puzzles. I either created puzzles or wrote papers as my assignments. My senior thesis was on the history of American word puzzles before 1860, which later was published in four installments in Word Ways: The Journal of Recreational Linguistics. As far as I’m aware, I’m still the only person in the world to get a college degree in puzzles.
So, did you plunge directly into the professional puzzling world once you graduated?
No. … I thought that a puzzle career would mean a life of poverty, that I’d be living in an attic somewhere churning out my little puzzles for $20 apiece. I actually wound up entering law school at the University of Virginia. My plan was to practice law for 10 years and make enough money to quit and do what I really wanted. But during the summer before I was to start law school, I did an internship with Penny Press, a puzzle magazine company in Connecticut. The whole summer was a blast. It let me see how I could support myself on puzzles, maybe not by making them, but by editing them. I did go ahead and complete my three years at UV to get my Juris Doctor degree. But I never took the bar exam and have no regrets.
How did you build a reputation in the puzzle community?
I became convention program director for the National Puzzlers’ League, which is the world’s oldest puzzle organization, formed in 1883, at age 23. I revived their dormant conventions. I brought the convention to my family’s farm in Crawfordsville, where my parents held a big outdoor lunch under a tent.
In 1978, I founded the American Crossword Puzzle Tournament in Stamford, Connecticut. It was the first such event in the United States in 50 years. It got a lot of publicity. I’ve continued to direct it, and it’s grown to 1,000 competitors. That same year, I became an editor of Games magazine.
In 1993, you assumed what is probably the top job in the field: crossword editor at The New York Times. Did that feel daunting?
Honestly, I was a little trepidatious, as I considered myself just a country boy. I wasn’t sure I was educated or cultured enough. The fact that my predecessor had been 36 years older than me didn’t help. However, by then I had been at Games for 15 years, and I knew the puzzle world thoroughly. I was the best person for the job.
Did you shake things up when you took the reins?
The first change I made was to add bylines to the daily crosswords. The contributors had labored anonymously up to that point. Also, I expanded the range of cultural references in the puzzle, brought in new, younger contributors, and I think added a greater sense of fun and playfulness. I wanted the puzzle to reflect the language and culture of everyone, young and old, who reads the Times.
In 2018, you received one of the highest honors that can be bestowed upon a graduate of Indiana University, delivering the commencement address. Did you handle it humorously or seriously?
Well, a little bit of both. I started my address by pointing out that the letters in “graduation” could be rearranged to spell “no drag at IU,” which I then said I hoped would be the case with my speech. Then I conducted a game. I named four well-known Indiana University graduates and challenged the audience to yell out guesses as to what their majors had been. The correct answers were all slightly unexpected. And that underscored my point, which was that it wouldn’t matter all that much in the end exactly what your particular college major was. If you get a good education, you can do anything in life.
