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constructing crosswords David Steinberg

“Crossword puzzles involve a significant amount of wordplay and creativity.”

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David Steinberg constructing Crosswords 01

David Steinberg was fourteen when he published his first crossword in the New York Times and became the second-youngest constructor to be published under Will Shortz’s editorship . Today he is 19, studies at Stanford University, and creates puzzles and crosswords for clients. We spoke with him about constructing crosswords, his experiences at tournaments, and of course his Pre-Shortzian Puzzle Project.


”Constructing Crosswords pays notoriously little!”

Why you are so interested in crosswords and puzzles – how did it all begin?

I’ve always been interested in letters and words, and I started solving jumble puzzles and playing Scrabble at a very young age. I constructed my first crossword for a 5th grade class project after seeing the documentary Wordplay. At that point though, I was more interested in Lego robotics, so I put crosswords on the back burner for a while. I saw Wordplay again when I was twelve (in 7th grade) and decided to make a crossword that didn’t break all the rules like the one I’d made in 5th grade!
The result was pretty terrible by my standards today, but I was proud of it at the time and I confidently sent the puzzle off to Will Shortz at The New York Times. Will rejected that submission and the next 15 I sent him, but he was very encouraging each time so I kept trying.

You were 14 when your work was first published in the NY Times – How did it happen?

Much to my delight, Will Shortz didn’t reject my 17th submission! Rather he said he liked the idea, but wanted some major revisions. At first I wasn’t sure I’d be able to fix the puzzle, because getting the theme to work required an entry with the letter pattern ?ISD. Luckily, there was RISD, which is short for the Rhode Island School of Design (a prestigious arts college near Brown), and everything suddenly fell into place. I sent the revision off to Will and soon thereafter received a much-awaited “Yes”. The rest is history!

Do you know Will Shortz personally? How did you meet?

I first met Will Shortz when he was giving a talk in the San Francisco Bay Area. My parents drove me all the way down from Seattle to see the talk, which was very exciting for me! I hadn’t yet had a puzzle published, but it was still an honor to meet Will. Since then, I’ve seen Will at numerous other crossword events, and I even got to look around his “puzzle museum” house while I was doing research for the Pre-Shortzian Puzzle Project two summers ago!

Is it possible to live from creating puzzles? How is it possible?

Yes, but doing so is very difficult, because constructing crosswords pays notoriously little! Editing jobs are hard to come by, and freelance constructing is hit-and-miss and ultimately not quite lucrative enough. The people who have made careers out of games and puzzle construction, such as Will Shortz, Mike Shenk, Matt Gaffney, Patrick Berry, and Trip Payne, are my personal heroes!

”Constructing Crosswords by using computer software made more sense”

You are creating your own crosswords – how do you do that?

I started out constructing crosswords by hand, as the late crossword legend Merl Reagle did in Wordplay, but I soon learned that using computer software made much more sense – especially for a young constructor with a very limited knowledge base! Much of the construction process is the same for hand constructors as it is for software constructors though. For themed puzzles my first step is to come up with an idea, which usually happens when I least expect it! I then think of theme entries that could fit symmetrically into a grid, which I proceed to design around these entries. Next, I work with Crossword Compiler, the software I use, to come up with all the nonthematic entries. Finally, I cue the puzzle up and submit it.

constructing crossword with software
David at his work constructing a crossword with computer software.


What does your family think about your work? Do they love crosswords too?

My parents have been very supportive of all my crossword ventures! They don’t love puzzles as much as I do, but my dad in particular has grown into a serious solver and my mom frequently helps him finish puzzles he gets stuck on. And every once in a while, they both get stuck and ask me for the answers!

What was your best crossword clue you have made up to now?

Wow, that’s a tough question–I have such a short-term memory for the clues I write! I guess I’d have to go with “Like pants on their last legs”.

Answer of the Clue



”I enjoy socializing with fellow crossword constructors, solvers, and editors.”

Please, tell us about your Pre-Shortzian Puzzle Project – Why did you found it? What is its main aim?

Before the Pre-Shortzian Puzzle Project, all 16,000+ New York Times crosswords published before Will Shortz became editor dating from February 15, 1942, to November 20, 1993 weren’t available online anywhere. They only existed in PDFs through a historical research database, where they were tough to find and decipher; also, they couldn’t be analyzed because they were just images. Over the course of four years, I led a team of more than 60 volunteers from around the world in digitizing the pre-Shortzian puzzles into a form where they could easily be analyzed and appreciated. Thanks to Jim Horne of XWord Info, all the pre-Shortzian crosswords can easily be viewed for free by anyone with an Internet connection now!

You also take part in tournaments. Please tell us why you take part. What were the best experiences that you have ever had in a tournament?

The biggest crossword tournament is the American Crossword Puzzle Tournament, an annual event in Stamford, Connecticut, previously Brooklyn, New York, which Will Shortz oversees. This past year I won first place in the C Division and came in 36th overall, my best finish ever. I go to tournaments in part for the fun of the competition, but mainly because I enjoy socializing with fellow crossword constructors, solvers, and editors. It is truly a pleasure to be a part of the warm and supportive crossword community!

How does such a tournament unfold?

Approximately 600 of the top crossword solvers in the world compete under timed conditions at the ACPT to finish seven previously unpublished puzzles as quickly and accurately as possible. The final three contestants from each of the top divisions (A, B, and C) get to solve an eighth crossword on big dry-erase boards in front of all the other competitors.

Do you like other games with words like Scrabble? Why? Why not?

Yes, I like Scrabble, Bananagrams, Words with Friends, and basically any other word game you throw at me! Crossword puzzles are still my favorite though, because they involve a significant amount of wordplay and creativity. Also, I enjoy learning something about all the words I use rather than just memorizing them, as is required for professional Scrabble.

You are 19 now – What are your wishes for the future? Do you have other interests?

I’m currently a freshman at Stanford University, where I plan to major in computer science, linguistics, or possibly some combination of the two. I’m also taking an economics course next quarter that I’m excited about, so I’ll have to see how that compares with my other academic interests. Outside of school and crosswords, I enjoy watching Cutthroat Kitchen and playing Hearthstone.

Thank you so much for your time and the answers of our questions, David! We wish you a good time at Stanford University and we hope that you can create a lot more crosswords!

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