When Will Shortz took over as the crossword editor at the Times, in 1993, he set out to make the puzzle younger. 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. 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. Part of his job, as he sees it, is to adjudicate what any puzzler should know. But he is a self-described “older white guy,” and his judgments have drawn criticism, at times, for catering narrowly to his demographic. To a rising generation of crossword enthusiasts, he is at once a revered maestro and a frustrating embodiment of the Old Guard.
Although 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. 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. 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. 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. Afterward, he sent me a few of his favorite crossword clues, which you can attempt to solve below.
We’re talking over Zoom, and you’re in your home, in Westchester. I’ve heard that you have a whole collection of puzzle-related ephemera up there. Are there any collector’s items you can tell me about?
I have what I believe is the world’s only copy of the first crossword puzzle in private hands. It’s the Fun section of the New York World from December 21, 1913.
What is it like?
It’s in the shape of a hollow diamond. The first word across was “fun,” that was filled in for you. 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. Still a flaw, I think.
Crossword puzzles have come a long way since 1913.
To put it mildly.
When did you first get into puzzles? Do you have an earliest memory of solving a puzzle?
I started making puzzles when I was eight or nine. I sold my first one, when I was fourteen, to my national Sunday-school magazine.
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. That was always my dream. 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. I remember adding up my figures, turning the page, and looking to see puzzle-maker on that list of professions. And not surprisingly, puzzle-maker was not there.
You went to Indiana University, where you designed your own major in enigmatology. I assume a lot of your studies were about the history of puzzles and making puzzles?
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. That’s how I made my first professional-quality crosswords.
Every course I took on puzzles was created by me. I took courses on mathematical puzzles, logic puzzles, the psychology of puzzles—which is, first of all, what’s going through our brains as we’re solving problems, and second, why do we as humans find puzzle-solving so compelling?
When I graduated from Indiana, I went to law school, because I didn’t think it was possible to have a career in puzzles. I was selling puzzles for ten and fifteen dollars each. You’re going to starve or worse. My summer between Indiana University and law school, I had an internship with Penny Press puzzle magazines in Connecticut. I realized this is how I could have a career in puzzles: by editing them.
You went on to work at Games magazine and eventually became the editor. My sense is that, for a lot of Gen X-ers, Games was the gateway to puzzles. I was a little too young to be the target demographic, but my older brother had all the anthology books, and they seemed very different from the dusty puzzle books in the library. What was the editorial ethos like?
Up until Games, the most prestigious crosswords appeared in the Times, but, in my opinion, and the opinion of a lot of people, the Times’ crossword was stuffy. The Times’ audience was older—probably the average age of solvers was fifties and sixties. The average age of Games readers was in the thirties, so it had a different vibe. A whole new generation of puzzle-makers came up through Games magazine.
It surprised me to learn that Games was at one point published by Playboy Enterprises.
My understanding is—this is oral history, now—that Hugh Hefner himself was a fan of Games, and, around 1982, Playboy Enterprises purchased Games and held it for a number of years. I think Playboy published three magazines then: Playboy, Oui, and Games. It was quite the combination. I remember we had a party once at the Playboy Club in Manhattan, which was ridiculous. We also got free copies of Playboy every month during their ownership.
Unlikely bedfellows! You took over as crossword editor at the Times in 1993. How did that come about?
My predecessor at the Times, Eugene T. Maleska, passed away in 1993, and they were looking for a new editor. I was thirty-six years younger than Maleska. I think I was hired partly because of my youth. I was the youngest crossword editor in the Times’ history. 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.
Today, almost all constructors use software to make crossword puzzles. The software doesn’t do everything: there’s still a human element in designing and filling the grid, and tinkering and writing the clues. But the arrival of software must have felt like a seismic shift. Along with the shift from analog dictionaries and encyclopedias to searchable online databases. Do you remember feeling that shift?
When I started at the Times, I think there was one person creating puzzles by computer. He had his own database, he had written his own program, but everyone else was making puzzles using graph paper and pencil. Over time, as electronic tools became available, more and more people started making crosswords with digital assistance.
Can you explain, in brief, how crossword-making software works?
So most crosswords, as you know, have themes. First you place your theme answers in the grid, then you place your black squares, sectioning off the grid into parts that you think you can fill in a lively way. And then you fill the grid. The crossword program will suggest a fill, which you can accept or decline. You can ask it to give you one word at a time, or a section at a time. Writing the clues comes last.
Do you think that crossword-making software changed the quality of puzzles?
Oh yeah. Crosswords today are so much better than they were even ten years ago, which are better than the puzzles ten years before that. The grids are more interesting and more colorful than ever before. You have less crosswordese and stupid obscurity, and more lively, colorful, juicy vocabulary. You can buy databases now that have been curated for interesting crossword answers, and that downgrade words and answers that are not interesting.
I also think the rise of crossword blogs and an online community has helped make crosswords better. When I started in 1993, the only feedback that constructors got on their work came from me, basically, unless they got it from a family member. Nowadays, if you have a crossword published, you can read dozens or hundreds of comments about it online, and that feedback has helped.
One of my great advantages I used to have as a crossword editor was my library. I have a really nice reference library for virtually any subject you could think of. Nowadays, there’s just so much information online that you can write more interesting clues.
I should say there’s still a strong human element to crossword construction. Only a human knows what an interesting answer is. Only a human can come up with an original idea for a theme, and only a human can write an original crossword clue.
Let me ask you, are you worried about ChatGPT?
I’ve played around with it, and it’s pretty impressive.
Yeah. I expect to use the program to help in puzzle-making. Right now, I have all sorts of books and specialized Web sites that help me find interesting answers, and I think this program may make it simpler. But can the program write an original, fun clue for a crossword answer? I’m dubious about that. Also, does the program know what an easy clue is? A hard clue? A medium clue? Will it be able to foresee possible difficult crossings for solvers and avoid those? I doubt it’s there yet.
In terms of writing fun clues, I will say I tried to get it to tell me jokes, and two or three would kind of land, but a lot of them didn’t even make sense. At least it’s comforting to know that computers are not the best comedians yet.
O.K., we still have a leg up.
You mentioned that, when you first got to the Times, the crossword felt stuffy. What was stuffy about it, and what kinds of changes did you make to try to modernize it?
The crosswords that were being published by the Times just before I took over were mostly made by older people. So they’re going to reflect older people’s vocabulary, knowledge, and culture. I wanted to keep the older generation of constructors, but I wanted to bring in new ones as well. I think the crossword should reflect the life, language, and culture of everybody who reads the Times, and that’s everybody from smart teens up to the oldest people.
Jack Rosenthal, who hired me—he was the editor of the Sunday magazine at the time—told me that, if any cultural reference appeared in the crossword from the most recent twenty-five years, it came as a shock. Of course, that’s not true anymore. Everything in life basically is fair game for a crossword, and it includes classical subjects you learn in school, like history, literature, geography, up to what’s going on in the world today: music, movies, TV, sports, and changes in language. So that’s one change.
Second change, the puzzles before me, I think, were a little staid. You didn’t see a whole lot of wordplay in the clues. Nowadays, there are a lot of playful clues that make you think of one thing, and it turns out to be something else. It’s like a joke snapping into place once you get the answer, and it gives you pleasure.
One thing that got a lot of notice, which I’ve considered pretty insignificant, was the introduction of commercial names in the puzzle. Before me, if “Oreo” ever appeared in the puzzle, the clue was always “Mountain: combining form,” which is preposterous.
“Oreo-” is some sort of Greek prefix meaning “mountain,” right?
Yes. I introduced commercial names, and there was resistance to that. But again, commercial names are part of life, and, if they appear in the news articles in the paper, then they should appear in the crosswords as well.
So, thanks to you, Oreo got a huge promotional bump from crosswords. I hope you’re getting a piece of that.
Wouldn’t that be nice?
You said that everything is fair game in a crossword. This makes me think about the “breakfast test” philosophy: the idea that a crossword shouldn’t make someone lose their breakfast, so to speak. The first editor of the Times puzzle, Margaret Farrar, once said that crosswords should avoid references to “death, disease, war and taxes.” It sounds like you have a different take.
I have never subscribed to the “breakfast test.” Of course the puzzle should be polite, but it should follow modern standards of good taste, and those have changed over the years. The word “ass,” when it appeared in crosswords in the old days, it was always the animal. Now there might be a polite way to clue it in terms of the rear end.
I remember I submitted a crossword to Will Weng, one of my predecessors at the Times, in 1975, and it had the answer “belly button.” And he returned the puzzle saying that was indelicate. So standards change over time, and the Times crossword has changed along with them.
Is it fair to say that you helped to relax those standards?
Yes. I think I have had a role in that. An answer that got controversy once was “scumbag,” which was clued in terms of the person, of course, but it has a literal meaning that’s really not nice, and some people objected to that. I was told by a higher-up, This is not a word you want to use again.
I mean, to me, the unobjectionable meaning has superseded the objectionable one —
That is my feeling, yeah. I remember early on I had the answer “brownnose” in a crossword. To me, the common meaning is so far removed from the literal origin of the term that it’s not a problem. But some people who know the origin don’t like to see that in a puzzle.
Can you think of any entries or clues or themes that you outright rejected because you thought they would be too offensive?
Two that jump to mind. I rejected a puzzle that had “Mengele” in it, the World War Two German Nazi. I didn’t want him in a puzzle. Once somebody—this is hilarious, I think—sent me a puzzle whose theme was four anagrams of “Adolf Hitler.” And I’m thinking, You’re sitting down to make a theme for a crossword. What would be interesting and entertain people? And that’s what you come up with?
Nowadays, we have to be more careful of people’s sensitivities on political issues. We’re much more cognizant.
You’ve said that your all-time favorite crossword is one that the Times ran on Election Day, 1996. The way it worked was that you could write either “Clinton elected” or “Bob Dole elected” in the center row, and all the down entries crossing “Clinton” or “Bob Dole” worked for either answer. A lot of solvers were fooled into thinking that the Times crossword had—either correctly or incorrectly—predicted the results of the election before it had been decided.
Pretend that you hadn’t run that puzzle in ’96. If someone had pitched that same theme to you about the Biden vs. Trump election in 2020, would you have accepted it? Or do you think, because of how political discourse has changed and how, I imagine, a lot of Times readers are allergic to seeing Trump’s name in a crossword, you would’ve thought twice about that theme?
Yeah, I would’ve thought twice, or three times. I don’t know that I’d run the puzzle now. In 1996, it was playful. And, even if you were voting for Bob Dole or Bill Clinton, you didn’t feel animus toward the other side. You didn’t feel that the country was going to hell if your opponent was elected. Nowadays, we do feel that, so it doesn’t feel like a subject to be playful about.
I want to talk more about how these sensitivities have changed. One way into it might be talking about the way that we edit for difficulty levels, which I find to be one of the biggest challenges of the job. The Times crossword is intended to be easiest on Mondays and most challenging on Saturdays, so it gets progressively harder throughout the week. Do you get complaints from people saying the Monday puzzle was too hard, or the Saturday puzzle was too easy?
Yes, we get complaints like that all the time. When I started at the New York Times, I was getting complaints from some solvers saying I was making the puzzles harder than before, and from other solvers saying I was making the puzzles easier. And I was thinking, Make up your mind, either it’s easier or it’s harder! And later I realized, No, that’s not true. My style of puzzle was different. The puzzles were difficult in a different way.
There was more obscurity in the old days, more obscure words. But if you knew those obscure words, the puzzles were easy. My puzzles had less obscurity, but there were more playful and tricky clues. If you were clever and could see through those clues, then those puzzles became easy. So there’s no one definition of what easy is.
I also think now, compared with the nineties, there’s a broader awareness of how identity shapes a person’s vocabulary and the things that they know. And I mean everything from race and gender and sexual orientation to age, class, regional background. Sometimes for me, acknowledging that can feel antithetical to the work of crossword editing. Because, when we’re editing, we’re relying on a belief in some kind of canon or common culture, at least among the audience that we’re making puzzles for. I wonder how you think about that tension.
Wow, I think about that all the time. And I think about it with my colleagues. When I started at the Times, I was the editor, and I had an assistant to proofread and handle some miscellaneous tasks. Nowadays, the crosswords at the Times are a huge department. There is a manager, there is me as editor, and I have five colleagues who look at submissions, edit crosswords, and do all the sorts of work that goes into the puzzle. So it’s a collaborative thing, and it’s a pretty diverse group now in terms of age, gender, and race.
Of course we’re also trying to get diversity in terms of the contributors. I read widely, I think I consume culture widely, so I try to bring everybody’s language and culture into the puzzle. But I am who I am. I’m an older white guy, and I’m very aware that there are other backgrounds that should be brought into the crossword. The hope is that, as I said earlier, every solver feels his or her life, culture, and language is represented in the puzzle.
I saw an interview you did in The Atlantic—and this is a decade old, so tell me if your feelings have changed—but you gave the example of a grid that had “Lorelai” in it, and it was clued as “Rory’s mom on ‘Gilmore Girls.’ ” And you asked the constructor to revise the grid, because you didn't think that a Times solver should have to know that fact. How do you go about making those calls?
That’s tough. Every call is one of a kind. I have not watched “Game of Thrones,” but I’m aware of many characters and facts about the series from having read about it. There are facts about “Game of Thrones” that have seeped into a broader culture, that I expect people to know whether they have watched the show or not. And I didn’t feel there was that same level of importance and general awareness of Lorelai from “Gilmore Girls.” I think, since then, we have allowed “Lorelai” with that spelling, but at the time I didn’t care for it.
It’s a fair point, insofar as “Game of Thrones” objectively has a much larger audience than “Gilmore Girls.” But I could imagine a constructor replying that “Gilmore Girls” is a show primarily for and about women, and that, as a man, you’re probably less likely to be attuned to the show or its fan base.
Yeah. When I don’t know something in a puzzle, I look it up first and I try to get a sense of its importance and its general familiarity. I try to be aware of my biases and inclusive of other people’s lives and vocabulary. And I will mention “Lorelai” from “Gilmore Girls” has appeared in three Times crosswords now. So it’s something that I resisted but have accepted.
Here’s a current example, it just came up this past week. There’s a constructor who gave us the word “dispense” as an across, and coming down is “nur,” which is an Islamic term. None of us on the editorial staff was familiar with the term “nur.” You could change the “N” to an “R” and make it “disperse” and “R.U.R.,” as in the Čapek play, so that is my preference for the grid.
I think it’s better as an “R.” We’ll reach more solvers with that. But then there was the issue: did the constructor purposely choose “nur” and think that was a significant thing for people to know? And people would get it from the crossings. The clue for “dispense” would be really clear, and the other two across answers were readily gettable. In the old days, I definitely would’ve changed that to an “R.” Nowadays, we’re talking about it.
I have to be honest, I don’t know either of those words.
Well, I’m surprised you don’t know “R.U.R.,” because that’s the Čapek play—I know that sounds ridiculous—from the nineteen-twenties, but it does appear in crosswords a lot. And that play was the first appearance of the word “robot,” so it actually has some significance even today.
There’s a whole category of references like that known as “crosswordese”: names like Mel Ott or words like “etui” that are far more familiar to crossword solvers than to the general public. Are you more lenient about allowing in obscure words if they have a history of appearing in crosswords?
Yes. And I don’t say that with pleasure. There’s all levels of crosswordese. There are things like “S.L.A.”, used to appear in crosswords all the time, stands for Symbionese Liberation Army, the group that kidnapped Patty Hearst in the nineteen-seventies. Today that has absolutely no significance, so basically that’s banned.
“Inee” used to appear in crosswords all the time. It’s a kind of poison used by native South Americans. Extremely obscure. It hasn’t appeared in any English-language dictionary since the nineteen-teens, I think. So that’s banned. Then there’s things like Mel Ott: he appears in crosswords way more than he deserves. On the other hand, he was genuinely a giant in baseball, and he’s in Cooperstown, so he’s significant. That’s the sort of crosswordese I don’t mind quite so much.
And sometimes those words have to be in the puzzle as the glue; we don’t really have much choice.
Yeah, it’s a question of how much glue there is, what it’s setting up. If you can remove “etui”, it’s probably better to. But if “etui” is holding together some really lively vocabulary, or it’s essential to making a theme work, then I don’t have a problem with it.
Another challenge we face as editors is that all references—shows, books, people—go through ebbs and flows of cultural significance. Apart from “Lorelai,” do you have any other examples of references you once deemed too obscure for the crossword, that in later years you decided to allow in?
Peter Gordon sent me a puzzle in the nineteen-nineties that had “Oops I Did It Again,” which at the time was a No. 1 song by Britney Spears, across the middle of the diagram. Lots of hits come and go. Why would you put that in a puzzle when, three months from now, no one’s going to remember it? So I rejected the puzzle for that reason, but I said, “If it turns out ‘Oops!...I Did It Again’ has legs, try me again in six months.” And he did. And, by that time, that phrase had entered the national vocabulary, so I ran the puzzle.
That’s great. It also makes me think about how I’m always glad when someone with a crossword-friendly name gets famous. Like when Idris Elba got famous, that was nice, because “Elba” is fairly common in crosswords, and now we can clue it to something other than “Site of Napoleon’s exile.”
Right. A more recent example is “Enola.” For years—for decades—all we could do was clue the World War Two plane that dropped atomic bombs in Japan. Now we have “Enola Holmes,” which is a modern reference and lots of people know it.
Do you have any other examples of something you all disagreed on, and how you ended up resolving it?
“Aro,” which is short for “aromantic.” I did not know that. In the old days, “aro” appeared in puzzles as—I think it’s a root or some obscure word. But, nowadays, it’s short for “aromantic.” And I’m willing to use the word “aro” in that sense.
This has started coming up in our puzzles a lot, too—“aro.” I also had to look it up the first time I saw it. I had to be schooled by the younger people.
It’s hard to clue, because you don’t want to use the word “romantic” in the clue, because that’s the r-o of a-r-o. And yet it’s really hard to make it clear to solvers, if they don’t know it, without using “romantic.” So I think we just break the rule and use it in the clue.
I remember having this exact debate with my editorial team. I think we landed on a clue like “Someone who doesn’t get crushes.”
Yeah. There was another one that gave me agita. The answer was “ace,” short for “asexual.” I did not know that myself, and the clue was not helpful if you didn’t know it. I thought a lot of people wouldn’t understand it.
In the Twitter era, there are new coinages every day, and it’s fun to let those things into the puzzle. But sometimes clues can feel like they’re only talking to people who already know the word, and I don’t want that.
Exactly. I want solvers to try to appeal to everyone, and that homogenizes the product some. You smooth over the rough corners and, yeah, you lose the highs a little from the people who know “ace” and get that clever reference, but you then avoid angering and confusing people who don’t know the reference.
In recent years, a lot of women constructors and nonwhite constructors have talked about their frustration with putting references in their puzzles that their editors deem too obscure. In the spring of 2020, an open letter signed by several hundred puzzle constructors and solvers was sent to Eric von Coelln, the executive director of puzzles at the Times, that alleged “the systematic erasure of minority voices in puzzles.” Did this open letter, or the broader pressure campaign that it was a part of, make you see things differently?
Yes, and changes were made because of that letter. At the time that came in, there were three of us on the crossword editorial staff, and while we were diverse in terms of age, we weren’t diverse in terms of gender or ethnicity. The staff has increased since then, and it’s more diverse in both of those ways. The second biggest change that happened is that constructors now receive copies of their edited and typeset puzzles before they appear in print, so they have a chance to comment and ask for changes if they want. In the old days, I always knew that was a nice thing to do, but we simply didn’t have time. For most of the editorship it was just me and I was just barely hanging on getting my work done.
It really takes a lot of back and forth to write to constructors, show them their puzzle, get the feedback—and, whether you agree with the feedback or not, it requires a response. But the Times is committed to that. It makes for a better puzzle and happier constructors.
At certain points during your editorship, the percentage of female crossword bylines at the Times has been under twenty per cent, and the vast majority of published constructors are white. To help address that problem, the Times launched the Diverse Crossword Constructor Fellowship. This was the initiative of Everdeen Mason, who came on as the Times’ first editorial director for games, in 2021. Can you tell me about the fellowship?
The process is that, if you’re part of an underrepresented group and you’re interested in making puzzles for us, we will work extra hard with you to teach you and hope that you become a regular contributor.
There are Zoom meetings over the course of several months teaching the participants the different aspects of crossword construction: theme creation, grid construction, clue writing. And everyone in their inaugural class had at least one puzzle published. I thought it worked out great, and we’re going to do it a second year.
We’ve focussed on crosswords so far, but the Times publishes a whole array of puzzles and games. What has your role been in expanding those offerings? Are you one of the people—or the person—deciding which new games to introduce?
I’m in charge of print, so anything that’s in print is of my devising. Around 2016, the Times Magazine decided to add a second page of puzzles. I put three puzzles there. One was Spelling Bee, which has been a huge success online; I was the inventor of it for print, and I’m very proud of that.
I have to ask, what are your feelings about Wordle?
I am fanatical about Wordle. I first learned about it in January of last year, so it was already a fad, but I caught it early on and have been a daily solver since then. There was a time in October and November of last year when my average was three. My average has gone up since then. I think it’s 3.5 or maybe a hair under that. Crazy about the game. Love it. Play it every day.
Were you involved in the Times’ decision to buy Wordle?
Had nothing to do with it. Just a big cheerer.
At the height of the Sudoku craze, you published a hugely successful series of books of Sudoku puzzles. For some crossword fans, it’s probably fair to say, Sudoku is an object of disdain. Did you feel conflicted at all about getting in on the Sudoku trend?
No conflict at all. I like puzzles of all sorts. People who like crosswords like to have their knowledge and vocabulary tested, and people who like Sudoku like the purity of the logic challenge. And my experience is that they’re two vastly different groups of people. I’m one of the rarities who loves both.
Shifting away a little bit from puzzles and games: you’ve made lots of cameos in film and television. Everything from the Hallmark series “The Crossword Mysteries” to “The Simpsons” and “Brooklyn Nine-Nine.” I’m curious what it was like for you to transition from puzzle editor to celebrity. Did you have a performing or acting background at all?
No, I have no performing background. And I’ll add, I have no performing skill. When I was on “How I Met Your Mother,” they wanted a cocktail-party scene with some snooty New Yorkers, and for some reason they thought of me, so they invited me out. It was a blast. “Brooklyn Nine-Nine” was fun. There were crossword enthusiasts involved in the show, so that’s how I got invited. “The Simpsons” was interesting. First of all, isn’t it interesting how many characters on “The Simpsons” have crossword-friendly names? Short—Lisa, Otto, Bart. We use them all the time.
Moe, of course.
Moe, yeah. So, I was speaking in San Francisco, and a producer came up to me after my talk and asked if I would be willing to be on “The Simpsons.” I said, “Oh, yeah, that would be fantastic.” And about nine months went by, and I didn’t hear from them, so I thought, Oh, they’ve forgotten about me. But they hadn’t. They had been planning a show. The producer asked all of the writers to pitch ideas for what the story line would be. I was told there were six or seven people on the writing staff, and all but one of them was a Times crossword-doer. And the one whose pitch succeeded was the one who didn’t do crosswords.
It turned out great. There was a crossword in the show, and we tied it to the crossword that appeared in the Times on the day that the episode aired. We didn’t announce that until after the show. You had to watch the show, and say, “Oh, that was the crossword that I did in the paper today.” That was cool.
Do you get recognized from any of these appearances? Or maybe even your voice from presenting puzzles on NPR?
One of the nice things about being a crossword editor is that people don’t know what I look like. A lot of people know my name, but very few people know what I look like. I don’t know if you saw “Wordplay,” the 2006 documentary?
I did.
Right after that appeared, a couple of people noticed me. Once I was in a sushi restaurant in Manhattan, and someone recognized my voice. That just blew me away. It’s nice to be recognized for your work, but not so recognized that people are rooting through my garbage.
You’re in the sweet spot of celebrity.
Exactly.
You’re an avid table-tennis player, and you co-founded the Westchester Table Tennis Center. Are there things that table tennis and puzzles have in common, or do they appeal to you for completely different reasons?
Surprisingly, they’re both brain games. During a table-tennis match, you are trying to discover and exploit your opponent’s weaknesses while hiding your own.
Most people do crosswords as an escape from the rest of life. Since crosswords and puzzles are my life, my escape is table tennis. What the two things have in common is when you’re wrapped up in a puzzle—you know this feeling—you forget everything else in the world. And you feel a sense of elation when you complete a particularly difficult crossword. When you’re in a tough table-tennis match, you forget everything else in the world. And, when you’re done, especially if you’ve done well, you feel elation and you’re ready to go back to the rest of life’s challenges. So I play table tennis for the reason most people solve crosswords.
During the pandemic, I imagine it was tough to play.
I don’t know if you know this: I have played table tennis literally every day since October 3, 2012. I even played during the pandemic, because I own the club. We closed for three months, but I always found someone who was willing to play with me.
I can tell you lots of stories about the challenges of keeping a streak like this. Six or seven years ago, the World Puzzle Championship was held in Bangalore, India. I’m the chairman of the World Puzzle Federation, so I help oversee the event. You cannot fly from New York to Bangalore without missing a day in the calendar. So I flew to Dubai and stopped there for two and a half days, played table tennis at clubs there, and then flew on to Bangalore. I’ve been to China and Japan multiple times, and, because of the time change, the flight leaves New York at, say, 11 A.M. and gets to China or Japan late afternoon the next day. So I play early in the morning, like seven or eight, go directly to the airport, fly to Beijing, get off the plane, and go directly to a club to keep my streak alive.
That’s dedication. Other than table tennis, what do you do to relax when you’re not doing your puzzle job?
I love politics and reading. Don’t ask me what books I read. I read voraciously, but mainly online: the Times, the Huffington Post, articles linked to at news.google, 538.com. As well as the crossword blogs.
I’m in a serious relationship for the first time in my life. That’s a whole other story. It started a little over a year ago. My partner and I moved in together in October, and life is sweet.
That’s great. Is your partner also a puzzle person?
Nope. Table-tennis person.
That probably works out even better, right?
Even better.
Are you evenly matched skill-wise?
I was the better player when we started, and now my partner’s a little better than me. But we’re close.
I’m struck by the wonderfulness of finding love at seventy. Would you be open to talking more about that?
I never expected to find love at my age, never expected to have a relationship like this. This guy is the perfect person for me, the only person in the world I think I would be partners with. We match in so many unusual ways. I don’t really believe in fate, but our connection feels like fate.
Why do you think it happened now? Was a relationship something you weren’t really interested in before?
I’ve never come out publicly. I’ve told lots of friends, but I’ve never been public about my sexuality. I’ve known that I’ve been interested in guys my whole life, but it wasn’t a life I wanted to lead. First of all, I was in denial for years, and I fought my inclinations. By the time I was in my thirties, I accepted the way I was. But I didn’t want to have a gay life style, if that’s how you put it. I have a wonderful career. I have a wonderful life. I have great friends. This wasn’t something I needed. It just dropped in my lap when I was sixty-nine and I thought, Wow, this is amazing. We’ve moved in together, we own a house together, and our intention is to get married, maybe this year.
This is one of my last questions. You’re coming up on three decades at the Times this year, right?
Yeah. My thirtieth anniversary is coming up this November. I’m crazy about the job. I love the creativity of puzzle editing. I feel I’m always learning stuff. I laugh a lot. And I love puzzle people, because they are interesting, smart, creative, witty people. I direct the American Crossword Puzzle Tournament, which is coming up soon, and that is my family. I get together with all these friends. That’s why I started the event.
It sounds like you’re nowhere near being tired out by it all, but I’m curious if there will come a time when you’ll want to spend more time at the table-tennis table, or whatnot. Do you have a succession plan in place?
The Times has very talented crossword staff, so, from this standpoint, there is no problem with succession. Of course, I plan to be around forever. I love the job, and I don’t plan to quit on my own.
You’re sticking it out until at least the fortieth anniversary.
I’m sticking it out until I come out horizontally. ♦
An earlier version of this article misspelled a magazine title and misstated the number of complimentary issues Playboy gave to employees of an affiliate magazine.
