How the New York Times Crossword Editor Constructed His Dream Career

From an Inside the Times story by Deb Amlen headlined “How Will Shortz Constructed His Dream Career”:

When a young Will Shortz turned in a middle school essay about what he thought becoming an adult would be like, his teacher was certain that he had not understood the assignment. His goal of becoming a “professional puzzle maker” had little to do with the adult responsibilities the teacher was hoping to read about. He was given a B+.

On Nov. 21, Mr. Shortz will celebrate his 30th year as the Crossword editor of The New York Times, so he may finally be able to shake off that early hint of skepticism. With his self-designed Indiana University degree in enigmatology — the scientific study of puzzles as related to semiotics, culture and cognition — a 15-year stint as the editor of Games magazine, his founding of the American Crossword Puzzle Tournament, a 30-year tenure at The Times and his weekly appearances as the puzzle master on the NPR program “Weekend Edition Sunday,” it’s safe to say that he is as entrenched in professional puzzle making and editing as anyone can be.

But how did he get that cool job?

There have been only three other New York Times Crossword editors since 1942, when the paper decided to publish puzzles in its magazine as counterprogramming to the news about World War II. Mr. Shortz became the fourth in 1993.

Each of his predecessors brought something valuable to the Crossword, Mr. Shortz said. Margaret Farrar, the first editor, had established the rules of modern crossword construction and increased the quality of the entries and clues; Will Weng, the editor from 1966 to 1977, brought a touch of humor to the clues and increased the number of themed puzzles published; Eugene T. Maleska brought a new level of rigor and sophistication to the puzzles.

Mr. Maleska, the cantankerous editor who had held the job since 1977, died in August 1993, and Jack Rosenthal, the Times magazine editor, was looking for a replacement. The other candidates were decades older than Mr. Shortz, who had just turned 40.

“Jack Rosenthal liked my age,” Mr. Shortz said. “I think he foresaw the digital revolution and that it would be helpful for The Times to have someone who could bridge the generations.”

When asked by Mr. Rosenthal what he would like to do with the Crossword, Mr. Shortz remembered saying, “I want to maintain the quality and intellectual rigor of the Crossword. But I would also like to bring in young contributors, fresher themes and more modern vocabulary.”

On Sunday, Nov. 21, 1993, Mr. Shortz made his debut as the Crossword editor, publishing Peter Gordon’s puzzle “Spectral Analysis,” a grid that was certain to shock the old guard of solvers. (Note to readers: This puzzle can be solved online, but you may want to print it out and use your crayons.)

When Mr. Shortz joined The Times, he introduced changes that he felt made solving more fun and accessible. Unlike Mr. Maleska, Mr. Shortz allowed well-known, national brand names in puzzles, which at first garnered considerable pushback from solvers who did not want to see the Crossword become commercialized.

But, Mr. Shortz said, he wanted the content of the crosswords to have lasting cultural significance, which he defined as “at least five to 10 years.” An entry that he felt was not familiar to a majority of people and did not seem to be something that would be discussed for long might not make it into a puzzle, he said, but if the topic was still on people’s minds six months later, he might then allow it.

Fresh minds, better puzzles

The expansion of the puzzle editorial team in recent years has made these decisions easier for the 71-year-old Mr. Shortz.

He was used to making the calls of what was acceptable in the puzzles by himself, but now he is joined by a diverse group of Crossword editors, which includes Joel Fagliano, the digital puzzles editor and lead constructor of the Mini Crossword; Sam Ezersky, who also edits the Spelling Bee; Tracy Bennett, who performs double duty as the editor of Wordle; Wyna Liu, who makes the Connections boards; and Christina Iverson, who writes the Easy-Mode clues for the Friday puzzles.

A group of testers that is varied in terms of gender, race and culture provides regular feedback. Constructors now have the opportunity to weigh in on any changes that are made to clues. In addition, Everdeen Mason, the Games editorial director, contributes her thoughts and looks over every puzzle.

The expanded team means that the crosswords now include things that may have been overlooked in the past, and that a wider audience can see themselves reflected in the puzzles.

Kera Bolonik, a writer and editor in Brooklyn, solves the Crossword every day and has noticed the changes and efforts being made in the wording of clues and more diverse references.

“These words have been around awhile, but there was a time when they would have been dismissed,” Ms. Bolonik said. “I think there could be more references to more cultural figures over a broad spectrum, but the effort is definitely noted. I feel like there is more thought put into editing the puzzle.”

Mr. Shortz feels that solvers are experiencing a “golden age” of crosswords, largely because people who would not have considered making a puzzle in the past have better access to the “how-tos” of crossword constructing, as well as the software needed to make grids at a professional level. Puzzle makers can also obtain a much wider range of feedback if they read crossword blogs and comments from a wider range of editors and testers, whereas in the past, the only communication the constructor had was with the editor.

As a result, quality standards have risen at The Times. “There are puzzles from years ago that I probably wouldn’t accept today,” Mr. Shortz said.

His favorite part of editing a puzzle is still the interaction he has with the constructors. “They tend to be interesting, smart, very talented people, often with flexible minds, good sense of humor,” he said.

The social aspect of puzzle making has always gone beyond the digital and print realms for Mr. Shortz. He recently donated the 47-acre property his family owned in Crawfordsville, Ind., to the city for the development of a park, which includes plans for a permanent puzzle scavenger hunt along its winding trails. And it wouldn’t be a Will Shortz project without a few outdoor Ping-Pong tables near the entrance as a nod to his nonpuzzle passion.

“I’m doing this to give back to Crawfordsville, a place I owe so much to,” Mr. Shortz said. “Also to honor my parents, who bought the property in 1951, as well as my brother and late sister.”

When asked what wisdom he might bestow upon the Will Shortz of 30 years ago, he laughed and said that he would rather talk about a piece of advice that someone gave him when he took the job at The Times.

“Don’t let the criticism get to you,” Mr. Shortz said. “Solvers feel that they have a personal relationship with the puzzle and with the editor, and they will not hesitate letting you know” when you have made a mistake.

That’s not to say that the feedback should be ignored, he explained. “Criticism is important, and you should consider it,” he said. “But don’t take it personally, and keep doing what you’re doing.”

Mr. Shortz still likes to make his own decisions about the puzzles that are published, but today those decisions are filtered through the feedback from solvers, constructors, the other editors and the crossword blogs. And that’s just fine with him, he said.

“They’ve made me a better editor,” he said.

Deb Amlen, the crossword columnist and senior staff editor of Wordplay, believes that everyone can learn to solve the Times crossword. She is the author of the humor book, “It’s Not P.M.S., It’s You.”

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