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The story behind The New York Times’ largest and most ambitious crossword puzzle

On Friday, The New York Times Magazine dropped a surprise for crossword obsessives everywhere: its latest Sunday edition would include a puzzle-oriented special section of the newspaper called Puzzle Mania. Among the neat collection of puzzle maker interviews and number and word games is a particularly unprecedented challenge, a puzzle larger than any The New York Times has ever constructed. The 50×50, 738-clue monstrosity covers two entire broadsheet pages. It may take even experienced puzzle solvers many days to complete.

Jake Silverstein, the current editor of The New York Times Magazine, told The Verge that the goal of these special sections is to reimagine the possibilities of print. The magazine, which typically includes the paper’s weekend crossword as part of the insert included in the Sunday edition, gets free reign to use larger, standard broadsheet pages in The New York Times for these sections alone.

The goal is to take advantage of the tactile, aesthetic, and nostalgic qualities of ink on paper, at a time when the death of print news is but a foregone conclusion for publications whose digital operations cannot keep them afloat. We chatted with Silverstein about Puzzle Mania and the story behind the largest ever crossword puzzle to make it into the NYT.

This interview has been condensed for clarity.

What’s the origin of Puzzle Mania, and how does it fit with what NYT Magazine has been trying to accomplish lately?

The magazine group at The New York Times has been taking on a fun project of building and designing special sections of the paper that will delivered in print-only format, as a way to explore the potential and possibility and all of the capacities of print as a medium. The big broadsheet format is an interesting one, there’s a lot you can do on those big pages.

Back in August, we did one these special sections in the paper of an excerpt of a then-brand new novel, Colson Whitehead’s The Underground Railroad, which went on to win the National Book Award. We took a couple months off and came back with this special section. In 2017, we’ll be doing a lot more. They’re all dissimilar in subject, approach, and even design. What holds them together is that they’re specially designed and conceived of sections that try to create something surprising and delightful that are innovative for the newspaper format, using ideas that are more taken from the world of magazines.

How did a section dedicated to crosswords and puzzles in general come about?

We knew that puzzles would be a good fit for this project, and we also knew that puzzles are also have something inherent. Obviously there are digital puzzles, and many people use our crossword app — but there’s a print-centric quality to certain kinds of puzzles, particularly doing the Sunday crossword puzzle.

we recently hired a special projects editor at the magazine that is heading up these sections, Kaitlyn Roper. A lot of what you see on the page is Kaitlyn’s brilliance as a editor. We had the design resources of the magazine, the design department, and the resources of our photo department — a few of the puzzles involve photographs. But Kaitlyn was someone who came in recently, and a big part of her job is overseeing this special sections. She’s using a lot of the magazine resources to give these sections a magazine flavor.

There’s more in the section than just the giant crossword, right?

There’s more than 33 total puzzles in the section. There’s some minis. You’ve heard of I Spy? Walter Wager created an original I Spy puzzle for this that’s really cool. There’s sudoku, there’s spirals.

It’s for solvers of course, but it’s also just a celebration of puzzles too. There’s wonderful sidebars and interviews with the puzzle makers — how they got into puzzles, what writing instruments they use to solve puzzles. There’s a letter exchange between [crossword editor] Will Shortz and Margaret Farrar, the original crossword editor. There’s a lot of puzzle marginalia. it will be fun for people who are solvers and not.

I will say pièce de résistance is this crossword we’re calling the Super Mega, the largest ever in The New York Times.

Was there an entire team behind the Super Mega?

It was one guy, Frank Longo. There’s a nice interview with him. He wrote it, and Will edited it as he does all puzzles. But it’s Frank’s work.

It is designed to be a traditional Sunday puzzle, so it’s the most difficult of the week?

It’s a difficulty level Tuesday/Wednesday, but the sheer size of it of course means it will take a long time to do. It’s more difficult than doing a Tuesday/Wednesday. But we didn’t want it to be impossible to finish. We had this vision that people would — in the way some families will put out a jigsaw puzzle for the holidays — we thought some families would put out this big crossword.

So this is going to be print-only, even those who subscribe to the Times’ crossword app?

All of these special sections we’re doing, including the book excerpt, and then everything we do next year has a common theme: print-only. People who obviously have a print subscription are psyched. People who have a digital-only subscription are going to be annoyed and have to go buy it in the store.

There’s certainly something that we are making it less convenient by restricting it to one format, we’re aware of that. But once you actually do get your hands on it, it feels fun and tactile and special in a way that products that are produced for multiple platforms don’t. Those feel more spread out and less focused in a way

The print-only aspect of this is very unusual, for a big media brand to produce anything that is print-only is unusual. Part of the whole idea behind these print sections we’re doing is to explore the uses of print. We would never say that print is superior to other platforms in all cases, but we want to think about what does work better in print or has unique qualities in print.

What do you get if you solve the Super Mega, or is there anything incentivizing people to finish it?

There is a phrase that when you solve all the clues. There’s a phrase that you can reveal and you can send that phrase to an email address and Will Shortz will pick at random five winners who will get a free one-year subscription to The New York Times. If you know the print subscription, that’s not cheap.


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