Inside the Mind of a Puzzle Master

New York Times crossword editor Will Shortz stretches and stimulates brains one clue at a time

No matter who you are or what you are interested in, chances are good that at some point in your life, you’ve done a crossword puzzle.

Whether you enjoy flexing some nearly forgotten grade school education, prefer mind-bending word play, or just happen to be a pop-culture junkie, crossword puzzles are a form of entertainment that everyone can appreciate. But do you ever wonder who makes those puzzles possible?

Will Shortz is the crossword puzzle editor for The New York Times, and is arguably the most famous puzzle-master in history.

“I became interested in making puzzles when I was eight or nine,” says Shortz, who is now 65. “I sold my first puzzle at 14 to a national Sunday school magazine.”

While some would look at puzzle making as nothing more than a hobby, Shortz chose to pursue his passion for brain teasers and enrolled at Indiana University. As part of the university’s individualized major program, he designed his own curriculum and became the first—and only—person to ever receive a college degree in puzzles.

“I created my own courses,” he says of his education. “And then found professors who were willing to work with me.”

As part of his curriculum, he studied the psychology of puzzles, puzzle construction, and the history of American word puzzles.

Will Shortz speaks at a crossword tournament // Photo by Don Christensen

Will Shortz speaks at a crossword tournament // Photo by Don Christensen

Over the years he has gone on to not only head The New York Times’ puzzles, but has written books, appeared numerous times on TV, starred in the 2006 documentary “Wordplay,” and even provided the puzzle clues that the Riddler leaves for Batman in the film “Batman Forever.”

While he enjoys puzzles of all kinds, Shortz says that he has always had a special connection with crosswords.

“I love playing with words,” he says. “I enjoy the playfulness of it, and I enjoy using my brain. It is so genuinely fun when you figure out an answer and it gives the brain a jolt. It’s great.”

You might not think to put Shortz in the same category as musicians, actors, and storytellers who are more closely associated with their art form. But with the care he puts into them, Shortz’s crosswords and other puzzles are no less artful.

“What I do is create long-distance entertainment,” he explains. “When comedians get on stage and tell jokes, or musicians play a song, they get that immediate feedback from their audience. What I do is create a puzzle, then send it out into the world and allow people to experience it wherever they are.”

Being good at creating puzzles is partially a study of the mind and psychology of gamers. But there’s also an element of being savvy about your audience’s interests. This is something Shortz is very aware of in his profession.

“I like to be on top of things,” he says. “When people know about things that I don’t, I feel bad. But I read a lot, I talk to people, I see movies, and I feel very in touch with what’s happening in the world. But I’m also not a teenager, so there are certainly new trends and things that I’m not aware of that I have to look into.”

While making new puzzles is his profession, at his core Shortz is still just as much a fan of solving puzzles as he ever was.

“I love doing puzzles. If I didn’t love it anymore that would be really sad,” he says. “I don’t really do crossword puzzles as much, but I still really enjoy doing other puzzles.”

Will Shortz with Dan Feyer (left) and Mike-Shteyman (right) at the 2017 American Crossword Puzzle Tournament // Photo by Don Christensen

Will Shortz with Dan Feyer (left) and Michael Shteyman (right) at the 2017 American Crossword Puzzle Tournament // Photo by Don Christensen

As the puzzles editor for The Times, people often submit their own puzzles with hopes of following in Shortz’s footsteps.

“The only way to know if a puzzle is any good is for me to do it myself,” he laughs. “It’s a tough job, getting up and having to do puzzles every day.”

In terms of what makes a good puzzle, Shortz says there isn’t a one-size-fits all approach.

“It really depends on the audience,” he explains. “You need to know who they are and what connects with them. New York Times readers, for example, are typically smart, well-rounded, and have lively minds. It’s about putting yourself in the solver’s shoes and thinking of what kinds of clues and challenges will connect with them.”

Just because his audience likes a challenge, Shortz says, doesn’t mean he has to overcomplicate things.

“Crosswords are the most flexible form of puzzle ever invented,” he says. “We have puzzles that are just five squares by five squares, and that is extremely popular. It’s quick, but it still allows the solver to tap into that part of their brain that challenges them. They like it because it provides the maximum punch.”

Whether he’s bending minds at The Times, presenting his work as a special guest on “Jeopardy!,” or rubbing elbows with celebrity puzzle fans, Shortz’s skills are still in very high demand. But for a man who has dedicated his entire life to games, the accomplishment he feels as a puzzle maker is still serious business.

“The greatest pleasure you as a solver can have is tackling a challenge you don’t believe you can accomplish, and then doing it,” he says. “It’s just an immense feeling of accomplishment that is shared by everyone.”