Inside Will Shortz's Philosophy — Hard Only As Far As Fair

What is Will Shortz's design philosophy, in one line?

"Hard only as far as fair." That is Will Shortz's design philosophy. He has been the crossword editor of The New York Times since 1993, publishing a puzzle almost every day for over thirty years. A profile of his work describes his rule this way: for Friday and Saturday he makes the clues as hard as he can, consistent with being fair (UVA Lawyer, Fall 2005 source ↗).

The second pillar is his answer to why people solve at all. "One of the reasons we do puzzles is to put the world in order," he told a lecture audience. "Most of life's problems don't have solutions; we just muddle through and do the best we can. With a crossword, there is one perfect solution" (The Chautauquan Daily, July 2023 source ↗).

This piece reads ten of his own interviews, lectures and broadcasts, and lays out his philosophy, his obsessions, his admitted failures, his dilemmas and his influences. It is a study of the person, not a review of the work.

Who is Will Shortz, and what has he done?

Born August 26, 1952, in Crawfordsville, Indiana. He took a bachelor's degree at Indiana University in 1974, but in an unusual field: enigmatology, a major he designed himself. In his words, "I have the world's only college degree in puzzles" (NPR, November 12, 2023 source ↗).

He decided early. "In the eighth grade, when asked to write a paper on what I wanted to do with my life, I said a professional puzzle maker" (same interview). He also glosses the word itself: "It's an old word. Originally, it meant the study of riddles. It goes back to the 18th century."

He finished law school at the University of Virginia in 1977. He never practised; he became an editor at Games magazine instead. In 1978 he founded the American Crossword Puzzle Tournament. Since 1987 he has been the puzzlemaster of NPR's Sunday Puzzle. He became crossword editor of The New York Times in October 1993.Thumbnail of "Will Shortz: An Evening with the Puzzle Master" (YouTube / umnLibraries)

The form he edits is forty years older than he is. The crossword began with the diamond-shaped grid Arthur Wynne printed in a newspaper in 1913 (The crossword, 1913). Shortz's work is not invention. It is publishing that form, again, every day.

What should a good puzzle do to the solver?

His answer is blunt. Let them solve it — but not easily. "The goal of the puzzlemaker is to get you to solve the puzzle, but only after a struggle" (Index Magazine, June/July 1998 source ↗).

In the same interview he carries it further: "The puzzlemaker wants to twist your brain to the very end, and then, finally, you understand it and you fill in all the squares. That's when you get the most satisfaction." Satisfaction, in this view, comes from resistance stretched to the last moment, not from the answer itself.

That is why the difficulty is tilted across the week. "They increase in difficulty. Monday is what you might call an easy/medium puzzle. And it builds up to extremely hard on Saturday" (same). The 1998 description still holds today.

What matters is that the slope has a ceiling. As the profile describes it, Monday clues are made as easy as he can, consistent with keeping them fresh; Friday and Saturday, as hard as he can, consistent with being fair (UVA Lawyer, 2005 — the reporter’s wording, not a direct quotation). Difficulty is not a free-standing dial. The ceiling comes first, and difficulty moves only underneath it.Thumbnail of "Will Shortz Reveals How To Master The New York Times Crossword Puzzle" (YouTube / Business Insider)

He also breaks down where difficulty comes from. "Most important is the puzzle's inherent difficulty; a crossword using obscure words is going to be harder... A crossword that has just a few black squares and lots of white squares is harder because the words are longer" (same). Not only the wording of clues: the density of the grid is itself a difficulty setting.

What has he been repeating for over twenty years?

First, freshness of vocabulary. "I'm looking for fresh, colorful vocabulary that is generally familiar to New York Times readers" (Virginia Law Weekly, January 24, 2018 source ↗). Good crossword vocabulary, he says, is "modern, lively, colorful, something that wouldn't have appeared in a puzzle ten years ago."

Second, the matching dislike. "Crossword-ese is vocabulary that people know mainly from crosswords, not from real life" (same). In 1998 he put it harder: "I don't like stupid obscurity. If there's a clue like '50-mile river in Rumania,' in an otherwise terrific puzzle, I may rework a corner to get rid of that."

Third, he separates obscurity from misdirection. Making a puzzle hard with rare words he dislikes. Making the solver read a clue the wrong way, he embraces: "I use every misleading opportunity I can" (CBS News, October 12, 2011 source ↗).

Fourth, no solving out of duty. "You shouldn't do the puzzle because you think it's good for you because that's a bore" (Virginia Law Weekly, 2018). It connects directly to what he told a lecture audience: "If you're using your brain all day to work, when you're done, you want to use your brain to play" (The Chautauquan Daily, 2023).

Put together, the four make one line. A puzzle is entertainment, not training — and because it is entertainment, it must never be made hard with boring words.

What failures has he admitted in public?

First, a misreading of difficulty early in his career. Of his Games magazine years he says: "They wanted hard puzzles, so I thought, by God, if these solvers want hard puzzles I'll show them how hard it is. I started making everything really hard, then got letters the other way" (UVA Lawyer, 2005).

The failure, read closely, is not that the puzzles were too hard. It is that he implemented the readers' words literally. The difficulty people ask for and the difficulty people enjoy were not the same quantity.

Second, the crossword of January 1, 2019. One of the printed answers was criticised as a slur against Mexican Americans. His first explanation ran: "Neither Joel nor I had ever heard the slur before — and I don't know anyone who would use it. Maybe we live in rarefied circles." That explanation itself drew heavier criticism (NBC News, January 2019 source ↗).

Days later, on air, he said it again differently. "That's right. It was a mistake to include that answer. It is, indeed, offensive. And I personally apologize" (NPR, January 6, 2019 source ↗).

What I notice is that the second statement carries no explanation at all. No context, no circumstances. Four short sentences. This is a man who insists on precision — "I'm talking about precision of language," he said of errors in clues (Virginia Law Weekly, 2018). Here that precision reads as being turned on his own apology.

Where does he say he is caught in the middle?

First, having to use what he dislikes. The man who dislikes crossword-ese also concedes it is necessary. "You get cornered as a constructor, and you've got this fantastic puzzle, and you have to use Oona, for example... You don't want Oona in your puzzle, but I think of it as like the mortar of building a house" (Little Village, September 10, 2013 source ↗).

Second, whether a crossword is a test or a game. He first reports the solver's view — "A crossword should not be a game, it's a test" — and then states his own: "to me, crosswords are also a game, and there's going to be trickery in the clues, and in the theme — that's just part of the modern crossword" (same).

Third, changing versus preserving. "I got a lot of it when I started in 1993, because I was 36 years younger than my predecessor, and there was a change of style, and I wanted to broaden the cultural references" (same). And in the same interview: "I just got a thoughtful letter from an unhappy solver a couple of weeks ago, who really longs for the days of my predecessor."Thumbnail of "Will Shortz & the Puzzling Sport of Crosswords" (YouTube / HBO)

On the third, his answer leans toward change. "Commercial names and brand names are part of life and the crossword should reflect life." "As language and the culture have loosened, the crossword should change as well" (Virginia Law Weekly, 2018). But he does not claim the letters stop arriving. The dilemma is not resolved; it continues.

Whom does he say shaped him?

The first name he gives is his mother. "My mother was a writer, so I think I got my love of words from her" (Virginia Law Weekly, 2018).

The second is law school. He never practised, but he is explicit about what those three years gave him: "The greatest benefit of Law School to me was to learn how to take apart a complex issue and deal with each part separately until you've solved it" (UVA Lawyer, 2005). It also reads perfectly well as a description of how to solve a puzzle.

The third is what he decided to inherit. According to the writer A.J. Jacobs, Shortz opened his job interview at the Times with what he would keep, not what he would change: "First, I told him what I wouldn't change – which is, the intellectual rigor of the puzzle" (Experimental Living, A.J. Jacobs, July 15, 2026 source ↗).

He also names contemporaries. In the 1998 interview he singles out David Kahn and Frank Longo as exemplary constructors of the day (Index Magazine, 1998).

Kizuki's reading — he designs the ceiling, not the difficulty

What follows is my own reading. It goes beyond what he has said.

I read Shortz not as a man who makes difficulty, but as a man who sets its ceiling. Difficulty almost never appears alone in his statements; there is always a condition next to it. Easy, consistent with freshness. Hard, consistent with fairness. The ceiling comes first, and difficulty is fitted underneath. The week's slope looks like the same ceiling relocated seven times.

Read that way, the brevity of the 2019 apology takes the same shape. A man whose job is drawing the line of fairness had missed what fell outside his own line. For that kind of failure, explanation does not help. So the second time, I think, he dropped the explanation entirely. That is my inference; he has not said it.

Finally, a habit of mine: lining up the dates. "I don't like stupid obscurity" (1998) and "Oona... is like the mortar of building a house" (2013) do not sit together comfortably. He concedes the necessity of what he said he would remove. But I do not read the fifteen-year gap as retreat. I read it as the compromise of a man who must ship seven puzzles a week without fail.

Where should you start to understand him?

Start with a Monday New York Times crossword. As easy as he can while staying fresh — that design is right there in the object. Solve through to Saturday and you feel the ceiling move.

Then listen to NPR's Sunday Puzzle. His solution to the constraint of radio is the interesting part. "Most puzzles are written, and you can't do that on radio." "Every challenge puzzle is something you can hold in your head and think about" (NPR, November 12, 2023). It reads as a worked example of puzzle design without paper.

For neighbours on this site: Maki Kaji of Nikoli, who placed puzzles in daily life as entertainment, and Martin Gardner, who turned consideration for the reader into a method. The history of the form itself is in The crossword, 1913.

Sources

Primary sources used in this article:

・Index Magazine interview (June/July 1998)

・UVA Lawyer, "Will. Shortz '77. Writes. One. Word. At. A. Time" (Fall 2005)

・CBS News, "Are computers killing crossword puzzles?" (October 12, 2011)

・Little Village, "Outside the box: An interview with Will Shortz" (September 10, 2013)

・Virginia Law Weekly, "Transcript of Will Shortz Interview" (January 24, 2018)

・NPR Weekend Edition (January 6, 2019 — the on-air apology)

・NBC News (January 2019 — his first explanation and the criticism of it)

・The Chautauquan Daily (July 2023 — report of his lecture)

・NPR, "NPR's puzzle master Will Shortz puts the pieces of his life together for us" (November 12, 2023)

・Experimental Living (A.J. Jacobs), "7 Things I Learned From Will Shortz" (July 15, 2026)

・Wikipedia, "Will Shortz" (used only to check dates: birth year, degree years, appointment years)

Video (used as images):

・"Will Shortz, master of puzzles and ping pong" (YouTube / CBS Sunday Morning)

・"Will Shortz Reveals How To Master The New York Times Crossword Puzzle" (YouTube / Business Insider)

・"Will Shortz & the Puzzling Sport of Crosswords (Full Segment) | Real Sports w/ Bryant Gumbel | HBO" (YouTube / HBO)

・"Will Shortz: An Evening with the Puzzle Master" (YouTube / umnLibraries)