Caetano Barreira / Reuters

Today’s Issue:

  • The Atlantic has a new crossword puzzle! Play it on
  • Caleb Madison creates the puzzles. In this issue, he tells us what puzzle solvers should expect from his crosswords: “a little bit of creative brain work, rather than just knowing facts.”
  • The less information a clue gives you, the harder it is, Caleb says. That distance is where the puzzle writer thrives. “The further you get away from the answer, the more fun you have.”

Caleb Madison Is Reinventing the Crossword

By Matt Peterson

How do you make something old feel new again?

That question occupies the mind of Caleb Madison, the creator of The Atlantic’s new crossword puzzle, which debuted earlier this month. He’s well suited to answer it. Caleb has spent the past decade making puzzles for the most traditional audiences—including the 800-pound gorilla of crosswords, The New York Times’—and the least. As the editor of BuzzFeed’s puzzle section, he inserted himself into clues in the first person and made a giant puzzle to end his run. All that, and he’s only 25.  

The puzzle Caleb writes for The Atlantic also straddles the line between tradition and innovation. For one, it’s a mini puzzle. While the standard Times puzzle fits in a grid of 15 squares across by 15 down, today’s Atlantic puzzle has just five squares in both directions. But that’s Monday. As the week goes on, the puzzle expands and the clues get harder.

As a crossword enthusiast, I wanted to know more about the mind I’ll be facing off against, so I called Caleb up. His answers to my questions have been condensed and lightly edited for clarity; my questions are in bold.

How did you come up with the idea of doing a mini puzzle that grows throughout the week?

Caleb Madison: When I was working at BuzzFeed, I experimented with a lot of different forms. I was young, and unconvinced that the crossword form had reached its final stage. A lot of the constraints and restrictions that have been applied to the puzzle since its inception have been because of space reasons. But today people like to solve on their phones. Now that you’re not solving in the paper every day, how does that change the experience? What does that make you want?

The mini crossword is nice because it’s less of a commitment. It’s still challenging, and still engaging and fun. But what I felt the mini had been missing was the sense of a narrative throughout the week that you could judge yourself against. You’re competing not only against your own time, but against a larger journey. I remembered the happiness I felt when I could solve a Wednesday puzzle for the first time, when I could solve a Friday puzzle for the first time. I missed that as an incentive. Hence, the idea to combine the two and hopefully get the best of both worlds.

You said you were unconvinced that the crossword form had hit its final stage. But what you’re doing now is not wildly different from a traditional crossword. Where did all that experimentation leave you?

Caleb: My motivations were to get people my age into crosswords more by showing them that the knowledge set required could be closer to their lived experience than they might think, rather than academic, crusty language. I work very hard to make sure that the vocabulary in these puzzles is varied from modern stuff to interesting, older stuff—and that it intersects. But I think the idea of changing the game, reinventing the form, was a little immature.

Not that there’s nothing new. For example, this extending mini, I don’t remember it being done before, and I’m really excited about it. But it’s very entrenched in the practice of the Times, which I love, and which obviously works so well.

What’s the identity of The Atlantic’s crossword? Does it have one yet?

Caleb: One of the things I’ve learned is not to come to a puzzle with too specific a view of what you want it to be, because it evolves based on what people are solving and what people like and what people don’t like.

However, my initial intention with The Atlantic was to make a puzzle that includes a lot of different types of knowledge in the same grid, so that you have modern pop culture crossing interesting old words crossing history. That’s the kind of pivoting that I think makes crosswords fun.

I try to make the clues funny. I’ve taken a little more liberty than The New York Times does in the informality of a lot of my clues. I have been doing a lot of punny clues that I think make sense to a solver but take a little bit of creative brain work, rather than just knowing facts. I’m trying to make the highbrow/lowbrow thing fun and snappy at The Atlantic, and I hope that’s working.

With the puzzles getting harder throughout the week, how do you calibrate difficulty?

Caleb: When you’re writing a clue, you become cognizant of what information you’re giving people and how good that information is. You’re giving someone either a synonym or a fact about the person, and then that synonym or fact about the person has a certain strength in its relationship to the answer, in its referent. You give a piece of information and that information has an amount of potent force by which to lead to an answer. You just make that force weaker every day.

The further you get away from the answer, the more fun you have—to be more associative, to be more playful. The field of reference that is, say, three steps away from this fact is a lot bigger than the field of reference that’s one step away from that fact.

I expect readers will develop a relationship with you like they do with The Atlantic’s other writers. What do you think readers are going to learn about you over, say, a year of doing your puzzles?

Caleb: I think you’ll get a general sense of my cultural world by the types of things that reappear. And maybe my sense of humor. I hope that throughout the year, as I keep writing these and develop a relationship with this audience, I can become a little bit more informal, which I like because I think that a lot of people don’t know that crosswords are written by people. They think they’re written by machines, or, I don’t know, God; they’re delivered in tablets to the newspaper every morning from on high.

There are all these indie crossword-puzzle makers who inject a lot of themselves, their personalities, and their values into these associative collages of clues and sentences and words. That’s what hooked me when I was younger. That made me excited to have this conversation with this person every day, or to play this game with this person every day.

As I get more comfortable, and as the audience gets more comfortable, there will be personality. Because I think it’s hard to separate my writing sensibility from the clues.

Here’s a link to the puzzle. Now get solving!

Today’s Wrap-Up

  • Today’s question: How are you enjoying the puzzle so far? If you’re looking for a place to start, Caleb mentioned the puzzle from Wednesday, October 17. He’d particularly like to know how you enjoyed 2-Down. Send a note to and we’ll let him know.
  • What’s coming: Later this week, you’ll hear from Sigal Samuel, The Atlantic’s global religion editor, on the internment camps in China’s westernmost province, Xinjiang.
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