Writing By Gia Miller

Photography & Design by Justin Negard

When Will Shortz was in eighth grade, he wrote a paper titled “Puzzles as a Profession.” He received a B+. “That was the proper grade,” says Shortz. “The assignment was to write an essay on what I wanted to do with my life, and I wrote that I wanted to be a professional puzzle maker. It wasn’t that the dream was wrong. It was because the paper really wasn’t that great. She said I misunderstood the instructions. But looking back, I wonder what kind of eighth grader decides that’s their life’s mission?”

That answer is simple. The kind of eighth grader that majors in enigmatology (he designed his own major) and eventually becomes The New York Times crossword editor and NPR’s puzzle master.

Child’s play

Shortz, who now lives in Pleasantville, grew up in Crawfordsville, 1.______________on an Arabian horse farm, and he credits his older siblings (a sister 9.5 years older and a brother 7.5 years older) for furthering his interest in puzzles, thanks to their puzzle books. “My sister had a book called ‘We Dare You to Solve This!’ on her nightstand,” Shortz remembers. “When she went off to school, I would borrow the book, read it, and return it so she wouldn’t know I had used it while she was away. And then I would borrow it for longer and longer, and eventually I just kept it. I still have her book.”

“I also remember making a maze for my brother when I was really tiny, but he didn’t solve it,” Shortz continues. “He wasn’t really interested. But when brought his girlfriend home during college, I would run out to the car with a puzzle I made because she was willing to solve my puzzles. I was always so excited for her to solve my puzzle. That’s how she ingratiated herself into our family.”

Shortz says no one in his immediate family was “a puzzle person,” but that didn’t dissuade him. He sold his first crossword puzzle at the age of 14, and by 16, Shortz was a regular contributor to Dell puzzle publications. While attending Indiana University, he took advantage of a new program. “When I was a kid, I joked about majoring in puzzles, never imagining that I really could,” says Shortz.

“But Indiana University is one of only about a dozen schools in the country where you can literally make up your major. They have a program called the individualized major program, which my mom discovered; it was a new program at the time. So, I went up to the front office and told them I wanted to major in puzzles. I wasn’t really serious about it at that point, but the counselor, who was the head of the program, explained why this would be a difficult thing to do. I left that meeting absolutely determined that this was what I wanted to do.”

Crafting his major required creativity, especially when the university didn’t offer any courses on puzzles. This forced Shortz to create every course himself. His goal was to learn everything he could about puzzles. He searched for 2.__________________ in departments that were relevant to the classes he wanted to create and approached each one with his concept. “I found an English professor who liked crosswords and was willing to oversee my research and grade my papers,” Shortz remembers. “One of my courses was on crossword construction, and that’s where I made my first real crossword puzzle. Every few weeks, I would go into my professor’s office, sit next to him, and he would solve my puzzle and critique it. I also took courses on mathematical puzzles through the math department, a course on logic puzzles through the philosophy department, and one on crossword magazines with a professor in the 3.__________________ department. For that one, I bought copies of all the major crossword magazines, and we reviewed them. I even took a course about the psychology of puzzles where I learned what’s going on in the brain as we’re solving problems as well as what is it about human beings that we create problems to be solved? Why do we do this?”

Shortz learned there are several answers to that question. “It’s partly because we have lively minds, and we want to keep using them,” he says. “There’s a pleasure we get from solving a problem. We’re faced with problems every day in life, and most of them don’t have clear-cut solutions; we just muddle through the best we can and move on to the next thing. But when you’ve solved a crossword, a KenKen, a sudoku, or whatever, and you have filled in that last square, it gives you a rush. You feel great knowing you’ve conquered the world, and you want that feeling as much as you can.”

His most challenging course, Shortz says, was for his thesis, which focused on the history of American word puzzles before 1860. He used all the resources he could find, ranging from the print archives, microfilm and microfiche in Indiana University’s “massive library” to a grant he received from the 4._____________________________ that allowed him to spend five weeks there reading “everything I could find on puzzles.” After college, Shortz attended law school at the University of Virginia. His plan was to work as a lawyer for 10 years before becoming a puzzle maker.

Bar v. Puzzles

Shortz’s original plan never came to fruition. In fact, he almost didn’t graduate from law school. After his first year of law school, he spent the summer working at Penny Press and discovered it was possible to have a career as a puzzle editor. Shortz sat with the idea for a while, and during the spring of his second year, he decided to pursue his dream. He shared the news with his parents through one of his regular letters home.

“I told my parents I would be dropping out of law school at the end of the 5.________________,” Shortz remembers. “I wrote it sort of as a ‘by the way’; it was a casual thing near the end of the letter. I hoped the news would sort of slip by and they wouldn’t notice it much.” After a “longer than usual” delay in response, his mom’s reply finally arrived. Shortz says she “wasted no time; she got right to the point.” She told him it was a terrible idea to drop out of law school. She advised him to get his degree and do whatever he wants after that. “At the end of the letter, she wrote the perfect thing,” Shortz remembers. “She said, ‘Whatever you decide, Will, your father and I will love you.’ That was the perfect response. And I thought she had good advice, so I went ahead and got my degree.”

Near graduation, Shortz had a meeting with the placement office, per their request. They were concerned because Shortz had not gone on a single job interview. “She asked me if I had any plans for after graduation, and I said, ‘Yes,’” he remembers. “I could see her face brighten because I was going to help her statistics; I was going to have a job. Then she asked me who it was going to be with, and I told her I’d be working for Penny Press. I saw her write in her book, ‘Penny,’ comma, ‘Press,’ comma, and then she waited for the rest of the law firm’s name. I had to explain to her that I was going to edit crosswords for a puzzle magazine company.”

But it wasn’t a waste; Shortz believes law school helped his career. He says it trained his mind to take a complex legal issue and divide it into “separate strands” so he could deal with each topic individually. Plus, he says, it taught him to think more clearly. And, once he decided he would not become a lawyer, he chose to take classes that would benefit his puzzle career. For example, he took a course on intellectual property and wrote a paper on copyright protection for puzzles and games.

After Penny Press, Shortz worked at Games magazine for 15 years; simultaneously, he founded the American Crossword Puzzle Tournament, which held its 47th annual tournament in April in Stamford, CT. Then, in 1987, when NPR began its Weekend Edition, Shortz took on the role of NPR’s puzzle master for their Sunday Puzzle show, titled “Weekend Edition Sunday,” and he founded the World Puzzle Championship in 1992. Shortz continues to serve as founder/director and puzzle master, and in 1993, he became the fourth ever crossword editor for

6. _____________________________.

Master of games

When Shortz took over at The Times, he made some immediate changes. For example, he gave bylines to every puzzle maker; if everyone else at the paper had a byline, he reasoned, then they should have one too. And, he believed, they would do their best work if they knew their name was on it. “I also thought the crosswords should embrace everything in life, meaning everything that appears in The New York Times,” Shortz explains. “That includes current music, TV, movies, sports, politics—everything. So, I introduced that immediately too.”

Finally, although the concept of graduated difficulty over the week began under the original crossword editor, Margaret Farrar, who theorized that most people don’t have a job to go to on Saturday, so they could manage a more challenging puzzle, Shortz created a “steeper slope.” He says his Monday puzzles are “easier than they’ve ever been before, but my Friday and 7._________________ ones are harder than they ever were before.”

But he kept all the main rules in place. Every answer must be a real word or phrase, and and unchecked squares are not allowed in American crosswords. “It means that every answer, every square, has to appear in two answers, both across and down,” Shortz explains. “So, if you don’t know that rap singer in one direction, you might know that name from the Bible in the other direction; you always have two chances at that letter. We also don’t allow two-letter words in American crosswords. And there has to be an all-over interlock, which means the black squares will never cut off the grid into two or more parts. You should never have to stop solving and move to another part of the grid. You should be able to move your way through the entire grid.”

In addition to his jobs at The Times and NPR, Shortz has authored or edited over 750 books, including several on sudoku, where he is credited as discovering the puzzle’s inventor. He says it was a puzzle no one had solved (or perhaps cared to solve), but Shortz was determined. He knew the first sudoku puzzle appeared in a 1979 issue of Dell Pencil Puzzles and Word Games, but that magazine did not include bylines on their puzzles. However, they did have a contributors list in the front, so Shortz combed through his collection of over 25,000 puzzle books and magazines and pulled every issue of Dell Pencil Puzzles and Word Games he had from 1979 through the early 1980s. “I noticed that every time Sudoku appeared, there was one particular name in the contributors list,” he remembers. “There wasn’t a single issue that had this puzzle and didn’t have his name. So, by process of elimination, I discovered that Howard Garns was the inventor, and he was from my home state of Indiana. He was an architect in 8._________________ . I later heard from one of his colleagues at the architectural firm who remembered that when lunch came around, Howard would shut the door and sit at his desk eating and making puzzles.”

It’s personal

On February 4, 2024, Shortz’s life changed. He was working in his home office when he leaned to his left and suddenly realized he couldn’t lean back to the right. He was drooling out the left side of his mouth. “I’d never had a stroke before, and I didn’t know anyone else who had one, but I lost control of my body, so I just knew it was a stroke.” He also knew he needed to get to the hospital.

But first, Shortz needed to change into warmer clothes (he was wearing a T-shirt and shorts). He managed to walk into his bedroom and put on pants. Next, he decided to go to the bathroom, but when finished, he couldn’t flush the toilet; suddenly, he couldn’t use his left arm and leg. Then, he “sort of crumpled to the floor.” Shortz lay on the floor, unable to crawl, and contemplated his next steps. It took him about 15 minutes to “squirm” to his office, grab his phone and call his husband, who was there in three minutes. “I’m so glad I had a partner,” Shortz says. “He called the ambulance for me. I’m a very calm person, and I knew I would go to the hospital, but it was just nice having someone there with me. I felt calm about it all.”

The ambulance came, Shortz was rushed to Northern Westchester Hospital, and while he was waiting to be evaluated, his speech became slurred. Shortz was having a second, and larger, stroke. After a CT scan confirmed his diagnosis, Shortz received medication to dissolve the clots and minimize the risk of damage. Luckily, his strokes didn’t affect his cognition or language function, but Shortz stayed in the ICU for 10 days, and his husband stayed by his side.

Shortz began physical therapy immediately after leaving the hospital, but the stroke had damaged the right side of his brain, impacting the mobility on his left and causing him to remain in a wheelchair for several months. “Then I graduated to a wide quad cane—a cane with four prongs—and then to a narrow one. After that, I graduated to a regular cane, and now I do most of my walking without one. But I have what they call spasticity on the left side of my body, like my elbow and my fingers, especially, which are curled up now. And I also have some in my left knee. I can’t move my ankle up yet; I can move it down, but I can’t move it up, so I can’t walk naturally. I just sort of fling my left leg forward, but it’s not an actual way to walk. My immediate goals are to lift my arm on my own, which I can’t do yet. And of course, I want to walk naturally. Eventually, I want to be able to touch-type again; somehow, I will have to get rid of the spasticity in my fingers to do that.”

Shortz resumed his job at NPR about two months after his stroke, and he says at that point, you could hear the difference in his speech, which is “mostly back to normal now.” He resumed his role at The Times on 9._________________ 30. And while the stroke hasn’t changed his outlook on life (“I have two goals in life. One is to make the world a little better by being here, and the second is to enjoy myself. I’ve always done those two, and I still do them.”), he says he does want to change one important “fact” about stroke recovery.

“I read that all the recovery you get from a stroke is in your first six months, and then you’ll be whatever it is; your situation and condition now is where you’ll be for the rest of your life,” says Shortz. “And that’s not true, because I feel I’m improving as much now as I was six months ago.” Because he’s talked about his stroke on NPR, Shortz says he’s received “so many emails, letters and cards from listeners offering words of support. One guy wrote to me that he had a stroke 10 years ago, and after all these years, he’s still making improvements. So that’s going to be my philosophy on perseverance.”

And, finally, no story on Shortz would be complete without covering his other love: 10._______________________. The owner of Westchester Table Tennis Center, Shortz began playing the game as a kid, and as a self-identified “natural collector,” he says he probably has “one of the world’s largest collections of table tennis memorabilia.” Prior to his stroke, he played “every single day for 11 years” (learn more about this on our podcast), but he had to regain movement before resuming the game.

“I love the speed of the game,” Shortz explains. “I love the sound of the ball. It’s my favorite sound in the world. I love that you can never completely master the game; you can always get better. I also like the social nature of the game. Unlike tennis, where you’re across the court from someone and you can’t talk with them, with table tennis, you’re just nine or 10 feet away from the other person. You can talk during a game or between points. I love that. I love the fitness of it. I’m improving myself physically by playing after the stroke. I really believe that table tennis has helped me recover. I even play left-handed some of the time. I put the paddle in my left hand, and because I can’t move my left arm to play, I guide my left hand with my right arm. Also, I can’t move my legs yet as I play, but I crouch, and I do the correct stroke and put my body into the shot.”

Like puzzles, Shortz says table tennis is also a “brain game” because during a match, “you’re exploring your opponent’s strengths and weaknesses, trying to exploit their weaknesses while using your own strengths. So, it’s a game of strategy; you’re using your brain.” And for him, like puzzles, it’s a way to relax. “You don’t worry about your office mate, the bill that you haven’t paid yet, the problem your kid has in school, or whatever it is. You focus on the game. You do the best you can, and when you’re done, you feel relaxed, refreshed and ready to go back to everything else in life.”

Asked if he would do anything differently in his life, Shortz says the only thing he’d change is not waiting so long to have a relationship with another man. His husband, whom he met at the Westchester Table Tennis Center in the summer of 2021, was his first same-sex partner. “I grew up in conservative Indiana, and it was strongly frowned upon,” he explains. “But when I finally came out, there was no change in any of my friendships. When we met, I was 69 and he was 27, so there’s quite an age difference. We grew up in opposite parts of the world; he’s from 11._________________. In some ways, we are quite opposite, and yet our personalities are very similar. And also, we both love table tennis; that’s what brought us together.”

Other than his ongoing stroke recovery, life is perfect. “I am living the dream,” says Shortz. “I’m doing exactly the job that I love. I’ve got lots of friends, and I have this table tennis center that I love, and I’ve got this fantastic partner.”

To learn more about Will Shortz, check out our podcast, available on Spotify, featuring a separate interview from what you’ve read here.

Did You Know

One of the puzzles Shortz is most proud of was created for the May/June 1981 issue of Games magazine, and it was not a crossword puzzle. He called it the “Equation Analysis Test.” 

“I did equations like seven equals W of the AW, and you had to figure out what the W of the AW stood for,” Shortz explains. “In that case, it was seven equals Wonders of the Ancient World. I had 24 of those, and it was a full-page game in the magazine. Several months after that puzzle appeared, people began mailing me back my own puzzle. Someone had retyped it, pretending it was their puzzle, and people told me it was going around with their friends at school, and they thought I might be interested in running it. That year, Us Weekly magazine included my puzzle in their annual What’s Hot issue, so that was pretty cool. It was the only non-person to appear in their What’s Hot issue.”

Shortz solves puzzles in pencil. “I do it in case I make a mistake,” he says. “Then I can backtrack.”

The oldest puzzle book in Shortz’s collection is from 1533. Technically, it’s a collection of riddles written in Latin. “They’re not puzzles that anyone would want to do,” says Shortz. “Honestly, the puzzle might be two or four lines, and then they would use four to six pages to explain the answer. But if you need six pages to explain the answer to a puzzle, it’s not a good puzzle.”

During a 2018 interview with Bryant Gumbel, Shortz said he considers himself the “arbiter of what matters.” Why? Because he’s the one who decides what is worthy of appearing in a crossword. “I think everything that appears in a Times crossword should have lasting significance,” he says. “Back in 1999, when Britney Spears had her hit, ‘Oops, I Did It Again,’ a contributor sent me that as the middle answer across the grid. The song had just hit number one before he sent me the puzzle, and there are lots of number one hits that just come and go that we don’t remember. So, I said, ‘At this point, I don’t think that answer is worthy of a Times crossword. But if it turns out that this name enters the popular lexicon, try me again in six months.’ And he did, and I accepted the puzzle.”

Perhaps the most famous puzzle Shortz has published ran on November 5, 1996, the day Democrat Bill Clinton defeated Republican Bob Dole. The concept dates back to his days at Games magazine. “In 1980, Ronald Reagan and Jimmy Carter were running for president, and Jeremiah Farrell, a puzzle maker in Indianapolis, sent me a puzzle where one across could be either Carter or Reagan. Either one worked with the crossing answers, and the clue was ‘the winner of this year’s presidential election.’ I thought it was such a cool idea, but we couldn’t do it because we wouldn’t be able to print it before the election, but I wrote him back and told him it was such a great idea. So 16 years later, I’m at The New York Times, and Jeremiah remembered how much I liked that idea, so he did a similar thing with Clinton and Dole. This time, the first few answers were mine. For example, my first down clue was ‘black Halloween animal,’ and it could be ‘cat,’ forming the C of Clinton, or ‘bat,’ forming the first B of Bob Dole. And the next clue was ‘French 101 word,’ which could be either ‘lui’ or ‘oui.’ The next one was my favorite; the clue was ‘a means of support.’ It could be either ‘IRA,’ as an individual retirement account, or ‘bra,’ which is another form of support.”

This article was published in the May/June 2025 edition of Connect to Northern Westchester.