The 10,000 Days of Shortz

Wednesday, April 7, 2021 marks a major milestone for Will Shortz. It’s his 10,000th day as Crossword Editor at the New York Times. This means 10,000 daily crosswords and thousands more Variety puzzles for the magazine stamped with his name.

Much has changed since Mr. Shortz answered an ad in 1993. An unnamed entity was looking for a crossword editor. Shortz had already been the editor at the well-regarded Games Magazine for a few years. He had an inkling that it might be the Times, but he knew his style was a huge departure from their status quo. He gave it a shot, and you know the rest.

Eugene Maleska

The Times had been a latecomer to the crossword fad but by 1993 it was the most famous crossword publisher with the strongest reputation. Its editor since 1977 was Eugene T. Maleska. His style might not fly now but in his day, he was beloved. He was classically educated and erudite, with an overt Calvinistic philosophy, which perfectly fit the Times at the time. Solving NYT crosswords in those pre-Internet days meant keeping your dictionary and your atlas handy. Encyclopedia sets were probably used more for crosswords than anything else.

Maleska died in 1993 with no succession plan in place. The Times had a choice, one we see echoed in tensions today. Did they want to maintain their current style? After all, they had a winning formula. Or were they ready to embrace radical change to attract younger solvers who didn’t care what the longest tributary of the second-longest river in Venezuela is?

Shortz and I spoke a few years ago about his early days. He’d understandably felt a lot of pressure not to screw up what was, by then, an important cultural institution. On the other hand, he was determined to make his mark.

He immediately instituted major changes. Constructor names, not just the editor, would be published on each puzzle. Pop culture and common brand names would be allowed. Wordplay would take precedence over obscure facts. Difficulty would increase from easy Mondays to fiendishly difficult Saturdays, with Sundays somewhere in between. He introduced gimmicks familiar to Games readers but foreign to NYT solvers.

Shortz told me something I hadn’t considered. Maleska had been a one-man shop, and when Shortz took over, there was no one alive who had ever held the position that was now his. Without a natural mentor, Shortz had to figure everything out himself, all while under tremendous public scrutiny.

The Shortz Era began with a show-off stunt puzzle by Peter Gordon. People loved it. People hated it. Letters poured in. Readers complained after the first week that the puzzles were too hard. Shortz adjusted, which drew complaints they were too easy.

Shortz obviously settled in, and now 10,000 days later, he’s still at it. The Times is still the most important crossword publisher. Shortz is the most famous puzzler in America. Most of his crosswords are at least good, many are excellent, some are outstanding. We’ve grown accustomed to his editing style. The more NYT crosswords we do, the more comfortable we get with his sense of humor, his worldview, his imagination, his limitations, and his willingness or resistance to pushing controversial boundaries. He would be the first to tell you that it’s the constructors who bring the magic, but it is his choice of which submissions to run, which words and clues are acceptable, and what makes a crossword fun, that gives the Times its voice.

Working on XWord Info has given me a chance to review every single Shortz-Era puzzle and, with the benefit of hindsight, it’s easy to see how they have evolved. Change isn’t all due to him, of course. Many more people are constructing. Computers have made a huge difference. Social standards have loosened. While we won’t likely see PENIS popping up again soon, gentle naughtiness has given way to answers like BADASS, NOONER, and G-SPOT. Clues that used to go out of their way not to acknowledge non-traditional genders or preferences now point directly at them.

The biggest changes happening now have less to do with computers and more to do with cultural pressure. The young phenom Erik Agard is leading the charge to make crosswords more inclusive, both the ones he constructs for The New Yorker and, well everywhere else, and the ones he edits for USA Today. Agard and various bloggers and commenters on Twitter and Facebook want to hold Shortz accountable for what they see as his shortcomings. Change is slow but they’ve already pushed the NYT crossword into areas Maleska could not have imagined.

The questions being raised are valid. Why have clues and answers favored men over women? For that matter, why are there so few women constructors? Why is minority culture mostly ignored? What does “common knowledge” mean anymore?

These are interesting philosophical questions, but layer on top of that legitimate business concerns. How can the NYT attract new, especially younger, solvers and constructors, without alienating their traditional solver base? NYT crosswords is important business. Your Games Subscription helps fund reporting in every section of the paper.

Shortz has provided a great deal of delight to a great many people over many years. He has edited far more crosswords than any other NYT editor. To the delight of his fans and the chagrin of his detractors, he shows no interest in retiring, so we’ll be able to observe how he navigates the world where competition is heating up and where the only constant is change. It will be fun to watch.


  1. Some of the discussion here pushes into question whether crosswords are merely a diversion or if they’re art. Specifically, do crosswords have any of the same social obligations as other artforms? More on that in an upcoming post.
  2. Nitpickers will note that one of the 10,000 daily puzzles was not, in fact, edited by Will Shortz, and he should wait a day to celebrate. He did make the editorial decision to run that puzzle.
  3. Will Shortz is the boss. No question. But he has a team working for him that operates mostly unnoticed. We’ll explore that in an upcoming post too.
  4. The first six crosswords in February this year were all made by African-American constructors. This was clearly a reaction to that cultural pressure, and it was an eye-opener. People, places, and things that were out of my wheelhouse made me feel like the puzzle wasn’t aimed at me. Oh, right. That was the point.
  5. You can read Will Shortz’s thoughts on the milestone in this interview with Deb Amlen on Wordplay.


  1. Haven’t there been other NYX xwords that were originally from other sources (and so weren’t edited by Will Shortz)? For example just about a year ago they ran the final puzzle from the “Crossword Tournament from your Couch” which as far as I know had its own editors.

    Unless those were unused ACPT puzzles, but I don’t think so.

    1. Good point.

      The Lollapuzzoola puzzle from 2011 is the only crossword that does NOT have Mr. Shortz’s name in the byline. I infer that means he had more input on the others like the one you mention, but I don’t know for sure.

  2. In Will’s interview with Deb Amlen that you linked to, he says, “I read all but one of the daily crossword blogs…”

    I wonder which one he is referring to? Or maybe he is just trying to seed doubts into the minds of every crossword blogger (am I “the one”?)

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