‘Inside UVA’: Meet the New York Times’ Crossword Puzzle Editor, a UVA Alum

Will Shortz, crossword editor at The New York Times: I’ll tell you, in my third year of law school at UVA, the placement office noticed that I had never interviewed for a job. They were concerned about me, so the placement office called me in to see what was happening, and the director asked me if I had any plans after graduation. I said, “Yes, I have a job.” I could see her eyes brighten because I would help her statistics. She asked me where my job was, and I said I would be with Penny Press. I saw her write in her book, “Penny, Press,” assuming it was part of a law firm’s name. I had to tell her that this was a crossword magazine company and that I would have nothing to do with law.

Jim Ryan, president of the University of Virginia: Hello, everyone. I’m Jim Ryan, president of the University of Virginia, and I’d like to welcome all of you to another episode of “Inside UVA.” This podcast is a chance for me to speak with some of the amazing people at the University and to learn more about what they do and who they are. My hope is that listeners will ultimately have a better understanding of how UVA works and a deeper appreciation of the remarkably talented and dedicated people who make UVA the institution it is, including our alumni. 

Today, I’m thrilled to be joined by Will Shortz, a UVA Law alum, the editor of The New York Times crossword, and NPR’s puzzle master. Will sold his first puzzle at age 14 and earned a one-of-a-kind degree in enigmatology from Indiana University. He has been with The New York Times for over 30 years. He’s been the subject of a popular documentary, “Wordplay”; founded the American Crossword Puzzle Tournament; and has authored or edited more than 750 books of crosswords, Sudoku and other puzzles. Will is also an avid table tennis player and co-founded the Westchester Table Tennis Center. Will, it is a real pleasure. Thank you for joining us today.

Shortz: Nice to talk to you, Jim.

Ryan: It is really wonderful to have you here. I know you’ve recently been through a challenging time with your health, and I’m sure our listeners are glad to hear from you. I’m just curious how you’re feeling these days and what you’ve been up to lately.

Shortz: As you probably know, I had a stroke in February, and in my case, it was on the right side of my brain, which affected the left side of my body. I really could not do anything with my left arm or leg – they were incapacitated. But I’ve done rehab and continue to do rehab every single day. Now I’m walking again and have regained some functionality with my left arm. I’ve been doing puzzles again on NPR since April, and next week, I’m about to restart editing The New York Times crossword. Fortunately, my brain was basically unaffected by the stroke, so I’ve been making puzzles like crazy for the last few months.

Ryan: Oh, that’s great. I’m really glad to hear that. Let’s step back and go back to the beginning. Where were you raised, and when did you become interested in puzzles?

Shortz: Well, I grew up on an Arabian horse farm in Indiana. My mother was a writer, and I started making puzzles when I was very young. I’m not sure why, but my mom showed me how to submit my puzzles for publication, so that’s what I did. As you mentioned earlier, I sold my first puzzle when I was 14. I became a regular contributor to Dell puzzle magazines. When I was 16, I used to joke as a kid that I loved puzzles so much I would major in puzzles when I got to college – never imagining that I actually could do this.

Ryan: Yeah. So how did you pull that off? How did you come up with the major in enigmatology? And am I right that you are the only person to ever receive a degree in that field?

Shortz: Yes, and if there were another, I’m sure I would have heard about it. Indiana has this innovative program – I am told there are only about a dozen schools in the country that have it – where you can literally major in anything if you’re accepted into the individualized major program. So I devised an entire curriculum in puzzles. 

For example, one of my first courses in my major was crossword puzzles: the construction of crosswords. Every few weeks, I would go into my professor’s office. I found a professor in the English department who would work with me, and I would bring in a puzzle for him to solve. I would sit next to him as he did it, and then he critiqued it. That’s how I made my first crosswords. 

I also studied the history of word puzzles, the creation of mathematical puzzles, and the creation of logic puzzles. I even took a course on crossword magazines. My thesis was on the history of American word puzzles before 1860.

Ryan: So, when was the first crossword puzzle?

Shortz: The first one was on Dec. 21, 1913, in an old newspaper called The New York World. It was an immediate success. It became a weekly feature of The World. Then, in 1924, there were two young graduates of Columbia Journalism School, Simon and Schuster, who were interested in starting a publishing firm. One of them had an aunt who was a big fan of the crosswords running in The World. They rushed a collection of crossword puzzles into print in April 1924. It was the world’s first crossword book, and it not only launched a craze, but also launched the firm of Simon and Schuster. Their first success was with a crossword puzzle book. They were actually embarrassed about having their first book be crosswords because they wanted to be a literary publishing house and thought something as frivolous as crosswords would reflect poorly on their firm. But after it became a runaway success, they were happy to start putting their names on the book.

Ryan: So what brought you to law school? I mean, you did this degree focused on puzzles. Connect the dots for me – what then brought you to UVA Law?

Shortz: Well, a couple of things. My older brother is a lawyer. I didn’t think I could have a career in puzzles. I thought I would die of poverty. So my idea was that I would practice law for 10 years and then do what I really wanted to do, which was puzzles. 

I’ll tell you a couple of things. During the summer just before law school, and then during law school, I worked for Penny Press puzzle magazines in Connecticut as an intern, and that allowed me to see how I could have a career in puzzles. I wouldn’t have to do it solely by making puzzles, which is very hard – usually, puzzles don’t pay so well – but I could have a job editing puzzles.

I’ll tell you, in my third year of law school at UVA, the placement office noticed that I had never interviewed for a job. They were concerned about me, so the placement office called me in to see what was happening. The director asked me if I had any plans after graduation, and I said, “Yes, I have a job.” I could see her eyes brighten because I would help her statistics. She asked me what my job was, and I said I would be with Penny Press. I saw her write in her book, “Penny, Press,” for the rest of the law firm’s name. I had to tell her that this was a crossword magazine company, and I would have nothing to do with law.

Ryan: And so you never practiced at all?

Shortz: No, I never took the bar exam or practiced. I went right into puzzles. But, you know, I don’t regret my years at UVA, for several reasons. First of all, UVA is a wonderful place to be, and during my last semester at UVA, I was blessed to live on the Range, which was a great experience. And actually, law school is great training for the mind. It teaches you to take complex problems and issues, separate them into their threads, and deal with each one at a time. It made me a better thinker, so I’m very happy to have a law degree from UVA.

Ryan: Well, we’re glad to count you as an alum. And you came back not too long ago to give the commencement address at the law school, if I’m not mistaken.

Shortz: I did. Yeah, that was great. I turned it into a game, where I gave quotes from Thomas Jefferson and left off the ends of them. I gave different possibilities for how he might have ended the statement. Everyone at the graduation ceremony would take a guess at how he ended the sentence. Each one had a little moral for life. So it was not only fun to play, but I think it also had a point to it.

Ryan: And how did the audience do in guessing?

Shortz: Well, everyone had fun. Yeah, it was a good time.

Ryan: So how did you land the job at The New York Times? And you’ve been there quite a while.

Shortz: Yeah, well, I worked for Penny Press for a short while after I graduated from UVA, and then I became an editor – and eventually the editor – of Games magazine. But I left there in 1993 and started at The Times when my predecessor, Eugene T. Maleska, died. The position became open, and I applied for it. I think I was the natural person for the job because of my background. As you mentioned, I had founded the American Crossword Puzzle Tournament and had been selling puzzles for years and years.

I think they saw that there would be a revolution in publishing – this was in 1993 – and foresaw the change in publishing moving toward digital. It would help to have a younger person. I was 37 years younger than my predecessor. I was one of the few people who got along well with both the older generation of puzzle makers and the younger ones from my years at Games.

Ryan: How has the digital era changed the way people do puzzles?

Shortz: Wow, that’s a good question. It’s really changed crosswords quite a lot – and for the better, I think. When I started at The Times in 1993, the puzzles were solved only on paper. I remember once we started making the puzzles available digitally. Occasionally, there would be a puzzle with a crazy theme that we couldn’t present digitally, so it would appear only in print. For that day online, we’d run a past puzzle instead, which infuriated people who had paid for a subscription to get the puzzle digitally.

Now, more people probably solve the puzzles digitally than they do on paper, so we’re very aware of that. We try to make the solving experience online at least as good, if not better, than solving on paper.

Ryan: There has been an explosion of puzzles connected to The New York Times lately – Wordle, Connections, Spelling Bee, the mini crossword. Are you involved in any of those?

Shortz: Well, I’m the person who invented Spelling Bee. I don’t oversee it digitally, but I’m proud of it. The New York Times purchased Wordle from Josh Wardle, who invented it, so I wasn’t involved in that, but I play it every day.

Wordle is so popular partly because it’s so short – you know, it just takes a minute or two. Nowadays, life is so fast-paced. It’s very hard to carve out 30 minutes of your day to do the crossword, whereas Wordle just takes a couple of minutes. Then you can share your results with your friends. That’s made it popular.

You know, in the old days, when talking with someone new, a common question was, “What movies have you seen lately?” Nowadays, I find we often ask each other, “How did you do on Wordle?”

Ryan: That’s so true. I do think the sharing feature encourages people to keep at it. I’m on a text chain with my extended family, and everyone reports their Wordle scores and how long it took them to do the mini crossword. It’s a wonderful way of staying connected.

Shortz: Exactly, yeah.

Ryan: So, I was going to ask you about feedback from people doing the puzzle. My guess is you’ve gotten some interesting emails over the years about objections to particular clues or comments on puzzles. Am I right? Do you get a lot of feedback?

Shortz: Well, yes, definitely. In the past, the mail used to come to me personally, and I was encouraged to respond to everyone. But nowadays, there are a number of crossword forums online where people write their comments about puzzles – what they liked or didn’t like. Most people’s comments go there rather than to me personally now.

But I’ll tell you, back in the 1990s, there was a woman on Long Island who wrote to me. Her mother had recently died just a couple of days prior, and they were about to bury her. Her mother was a big fan of The New York Times crossword, and the woman wondered if it would be possible for us to get the following Sunday’s New York Times Magazine, which they could bury with her at the funeral. It would be a way for her mother to be happy through eternity.

There was also a gratifying story of a woman who wrote to me saying she had been solving The New York Times crossword for years. She had brain surgery and was worried about her ability to solve the crossword afterward. As soon as she regained consciousness, she asked for a copy of The New York Times crossword. She solved it, and it reassured her that she had come through the surgery OK.

Ryan: That’s a great story. Of all the puzzles you’ve created, do you have a favorite or a particular type of puzzle you enjoy solving?

Shortz: My favorite kinds of puzzles to solve are cryptic crosswords in the British style. But honestly, I enjoy any kind of puzzle – mathematical, logical, or word puzzles of any sort. I play Wordle and Connections every day. While I’m not involved in creating those, I direct the program for the National Puzzlers’ League Convention every year and take part in all of its puzzles. I also direct the American Crossword Puzzle Tournament. So really, I like any challenging puzzle.

Ryan: What is it about puzzles that you find so alluring, and why do you think people come back to them over and over again?

Shortz: Every kind of puzzle has its own appeal. For crosswords, it’s the love of language – this incredible English language that we share. I think English has more vocabulary than any other language in the world, and we incorporate all of that into our crosswords, as well as everything in life. You know, things you learn in school – geography, history – and modern topics like TV, movies, sports and music. Everything can appear in crosswords, so it’s an all-around test of your brain.

I think, as humans, we like to solve mysteries. Every puzzle is a little mystery we get to solve. And the biggest thing is that it gives us a sense of empowerment. Most of the problems we have in everyday life – we just muddle through, do the best we can, and at the end, we don’t know if we’ve gotten the best solution or not; we’ve just coped with life.

With a crossword, Sudoku, or some other kind of puzzle, we’ve seen the process through literally from square one to the end. When you fill in that last square, you feel a rush. It makes you feel great, like you’re in control of life. That’s what I think is great about puzzle solving.

Ryan: Yeah, that’s a great description. It is very satisfying. Tell me a little bit about your experience with the documentary “Wordplay.” What was that like?

Shortz: Well, it was in the fall of 2004 that a filmmaker, Patrick Creadon, in California, called me and asked if I would be willing to be part of a documentary about crosswords. I thought maybe 150 people would watch it on YouTube once it was done. But I thought, why not? Sure, I’ll do it.

They filmed at the 2005 American Crossword Puzzle Tournament and did a lot of interviewing with me and my colleagues. The film debuted at the 2006 Sundance Film Festival, where it was a hit, got picked up by a distributor, and was released in theaters that year. It became one of the 25 highest-grossing documentaries of all time.

It’s a great film. For anyone who hasn’t seen it, I’ll just say, whether you like crosswords or not, it’s a fantastic movie. It has something at the end – I don’t know – it still brings tears to my eyes every time I rewatch it.

Ryan: Do you ever have the equivalent of writer’s block when you’re creating a puzzle?

Shortz: Not really. I’m always thinking of puzzle ideas. I’d say I have a playful mind. When I’m lying in bed, going to sleep at night, I’ll play around with ideas in my head and come up with my best ideas that way.

It’s like being a writer. There’s always something new to write about. For a puzzle maker, there’s always a new twist on something or a new idea you can create a puzzle around.

Ryan: Do you have, looking back over your career, an all-time favorite puzzle that you’ve created?

Shortz: Yes, my all-time favorite puzzle is something called the Equation Analysis Test, which ran in the May/June 1981 issue of Games magazine. The way it worked was I took equations like “7 = W of the AW,” and those letters were the initials of the words that completed the equation. So “7 = Wonders of the Ancient World.”

Another example: “5 = S,” which would be “5 Senses,” or “31 = F at BR,” which would be “31 Flavors at Baskin Robbins.” You have these equations to solve.

The puzzle appeared in Games magazine, and apparently, people started liking it and photocopying it, taking away where it originally appeared, and giving it to their friends. Later, in 1981, people started submitting my own puzzle back to me at Games magazine, saying they’d seen this cool puzzle running around and asking if I’d be interested in publishing it.

Ryan: And remind me, when did you start as the puzzle master on NPR, and how do you like that compared to the other aspects of your work?

Shortz: I started in 1987 on a program called “Weekend Edition Sunday.” The original host was Susan Stamberg, who’s a longtime NPR presenter. Her idea was that this two-hour program on Sunday morning should be the radio equivalent of a Sunday newspaper. It would have news, features, and so on.

We all know one of the most popular features of a Sunday newspaper is the crossword. She wanted a puzzle on the show, so I thought about what kind of puzzle would work. Obviously, it couldn’t be a crossword because that requires writing, and it couldn’t be something very hard because you’d have long periods of silence on the radio, which you can’t have.

So I came up with this format where I give quick word teasers. Originally, it was just Susan, because she’s a puzzle solver and a lively person herself. Later, Liane Hansen became the host of the show, and she also likes puzzles. She had the idea to bring listeners into the show.

Liane was in an impossible position. If she answered all my puzzles quickly, she was a smart aleck, and if she couldn’t answer them, she looked bad. That’s a lot of pressure. But nowadays, listeners are part of the show. I love it because I love making puzzles. Every week, I make an original puzzle for the radio.

Ryan: Let’s talk about table tennis. How long have you been playing, and when did you first get interested in it?

Shortz: I grew up in Indiana, and my family had a ping-pong table in a rec room, so I grew up playing ping-pong as a kid. I have a whole bunch of trophies from high school. I’ve played almost my whole life, but I stopped for 15 years and then picked up the game again in 2001. I became progressively obsessed with it – playing two times a week, then three times, four times, and eventually seven times a week.

My best friend came from Barbados, and around 2006, we started going to table tennis clubs together. We decided to start our own club, which is in my hometown of Pleasantville, New York. It’s the Westchester Table Tennis Center.

We are the second-largest table tennis facility in the country, with 30 tables. We’re open until 10 p.m. every night, and we host the largest monthly table tennis tournament in the country, offering $8,000 in prizes every month.

I’m obsessed with the game. I’m the only person ever to play at a club in all 50 U.S. states, and I’ve played in 44 countries so far. In 2012, I decided I was going to play table tennis every single day. I had a streak that went for 11 years and four months – 4,141 days in a row – until I had a stroke earlier this year.

Now that I’m recovering from my stroke, I’m playing table tennis again, but I’m not going to restart the streak. I’ll just play as much as I want.

Ryan: And are you completely self-taught, or did you get coaching along the way?

Shortz: I was self-taught until relatively recently, so a lot of my training now is probably undoing the mistakes that are ingrained in me from before.

Ryan: Right. Do you see any connection between table tennis and puzzles other than obsessiveness?

Shortz: Surprisingly, they are related. First of all, they’re both brain games. Obviously, puzzle-solving is a brain game, but table tennis is, too. You’re training your body to perform at its best, and it’s a very fast-paced game with all kinds of spins and strategies. So you’re using your brain all the time.

I also play table tennis for the same reason that most people do crosswords and puzzles – it’s a diversion from life. If there’s anything worrying you, a crossword will help distract you. When you’re done with the puzzle, you feel great and ready to face everything else in life.

For me, since I do puzzles for a living, they don’t give me that same sense of relaxation. Table tennis is how I clear my mind at night.

Ryan: Well, Will, I want to thank you very much for taking the time. It’s been a real pleasure to speak with you, and I have to say, you made my mother very happy. She did The New York Times crossword puzzle every day and was a wiz at the Sunday puzzle.

Shortz: Oh, you had a good mother. Thanks a lot, Jim. It’s been a pleasure.

Ben Larsen, co-producer of “Inside UVA”: “Inside UVA” is a production of WTJU 91.1 FM and the Office of the President at the University of Virginia. “Inside UVA” is produced by Kaukab Rizvi, Benjamin Larsen, Mary Gardner McGehee, Matt Weber and Jaden Evans. Special thanks to Maria Jones and Jane Kelly.

Our music is “Turning to You” from Blue Dot Sessions.

You can listen and subscribe to Inside UVA on Apple Podcasts, Spotify, or wherever you get your podcasts. We’ll be back soon with another conversation about the life of the University.