I’m Will Shortz, New York Times Crossword Editor, And This Is How I Work

Will Shortz is the most prestigious name in crosswords. As editor of the daily New York Times crossword, he has worked on every puzzle since 1993. He’s also the founder of the World Puzzle Championship, the American Crossword Puzzle Tournament, and owner of the Westchester Table Tennis Center.

Shortz gave us a detailed look into the editing process for a Times crossword, which involves rewriting about half the clues. He talked to us about his custom college degree, showed us his editing desk, and named the website that stores every Times crossword answer in history.

Current gig: Crossword editor, The New York Times

Current computer: Mac 10.13.6

Current mobile device: iPhone 7

One word that best describes how you work: Playfulness

First of all, tell us a little about your background and how you got to where you are today.

I started making puzzles when I was 8 or 9 and sold my first one professionally at 14. I hold the world’s only college degree in Enigmatology, the study of puzzles, which I earned through the Individualized Major Program at Indiana University (1974). For 15 years I was an editor (and eventually the editor) of Games magazine. For the past 25 years I’ve been at the Times.

Take us through a recent workday.

Today was an editing day. My assistant Sam was with me. We edited a Sunday crossword, a Sunday variety puzzle page, and two weekday puzzles (Monday and Tuesday).

The Sunday crossword, unfortunately, required a lot of work. The theme was clever and the fill was excellent, but most of the clues were either too easy, too ordinary, too obscure (involving trivia that made me go “Who cares?”), unclear, or not good for some other reason.

For example, for the answer SALON, the contributor suggested the clue “Business that really blows?” That seemed nonsensical, besides being a little rude. We changed it to “Business that has cut prices.” We felt that had nice misdirection, while still being accurate and fair. For LEG the contributor proposed “Something to stand on,” which we felt was obvious and not particularly clever. We changed it to “Anchor, e.g.” — as in the anchor leg of a race. That’s appropriately challenging for a Sunday Times puzzle, while still being on target and fair. Altogether we changed about 60 per cent of the contributors’ clues. Basically, I don’t use any clue that my assistant and I don’t both like.

After each puzzle is edited and typeset, a pdf is sent to a group of test solvers, one of whom rechecks every word and fact after us. They all call or write in with their comments and corrections. All together, ten test solvers see every Times crossword before publication. I don’t think any other puzzle in the country goes through such rigorous editing and testing before publication.

What apps, gadgets, or tools can’t you live without?

My biggest tools are books. I have hundreds of references on almost every subject you can think of. Nowadays, of course, most information can be found online, and I spend a lot of time on the internet. But I know my books so well that it’s often easier and faster to look something up in a book than to do an internet search. In some cases books are more accurate than websites besides.

What’s your workspace setup like?

I have a second-floor home office, looking out on a quiet suburban neighbourhood with hills and trees. My desk is surrounded by dictionaries and other references. A computer at the side is for typesetting the Times puzzles as well as corresponding with contributors.

What’s your favourite shortcut or hack?

The website XwordInfo.com contains every New York Times crossword answer and clue back to the first Times puzzle in 1942. So I can look up previous clues to answers and, if possible, avoid repeating them.

Take us through an interesting, unusual, or finicky process you have in place at work.

I get more than 125 crossword submissions a week. I ask for them to be sent by postal mail, because I like to mark up the manuscripts, and it’s easier to do so on paper than on a computer screen.

Every submission gets looked at by at least two people. My assistants and I write our comments on the outside of the envelopes — what we like, what we don’t, whether we’re leaning yes or no — and then circulate them to the others. I make the final decision on each acceptance or “maybe.” Then one of us emails the contributor our response.

It’s a little old-fashioned a process, but I feel it’s the best one for what we do.

Who are the people who help you get things done, and how do you rely on them?

I have two assistants in their 20s, Joel Fagliano and Sam Ezersky. They’re both brilliantly talented, and sometimes they know things I don’t.

How do you keep track of what you have to do?

There are weekly deadlines for turning in puzzles to the Times, so my work schedule is planned backward from there. Each puzzle is edited, typeset, sent to solvers for testing and rechecking, then polished and eventually sent electronically to the Times. On average about half the clues in the published puzzles are mine. As time permits my assistants and I answer mail.

How do you recharge or take a break?

I own my own table tennis club, the Westchester Table Tennis Center, where I play every day after work. Table tennis serves a purpose for me that crosswords do for others: When I play a match, I focus completely on the game and forget everything else in the world. When I’m done, I’m relaxed and refreshed and ready to go back to everything else in life.

What are you currently reading, or what do you recommend?

You happened to catch me while I’m reading Dreyer’s English: An Utterly Correct Guide to Clarity and Style. But in another day or two I’ll probably be on to something else.

Who else would you like to see answer these questions?

Bill Clinton.

What’s the best advice you’ve ever received?

Pick an occupation in which you don’t mind the least interesting part. For me typesetting is the least interesting aspect of crosswords — and I love to type. So I’m happy!

What’s a problem you’re still trying to solve?

How to squeeze 25 hours into a day.


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