University of Chicago student Garrett Chalfin tells us how he created New York Times Sunday crossword puzzles

At 19, Garrett Chalfin has landed his second crossword puzzle in a Sunday edition of The New York Times — an impressive feat for a cruciverbalist of any age. 

Chalfin — whose puzzle also appears in Sunday’s Chicago Sun-Times — worked on it for more than a year before submitting it last spring, during his senior year of high school.

A New Yorker who’s now a first-year student at the University of Chicago and figuring out what to major in, he balances puzzle-making with classes.

This is his fourth puzzle, second for a Sunday. He has five more puzzles that have been accepted and will be running in the future. 

When did you start creating crossword puzzles?

At summer camp. I went to a very sporty athletic camp, and I was a nerdy, academic child. I got along quite well with my sportier peers, but we didn’t really have an activity that we could both partake in and enjoy. I found that solving crossword puzzles was a good way for us all to connect and have fun together. 

Even though I was maybe 12 or 13 at the time, I said, “What if I make one?” So I made a very crummy crossword puzzle and sent it to [New York Times puzzle editor] Will Shortz, and it was politically but very quickly rejected.

Then, during COVID, I had some more free time on my hands, and I was bored in June of 2020. I was just scrolling on my computer and seeing if there were any things for me to do, and I came across the crossword software I downloaded those years ago. I started playing around with it again.

What went into this puzzle?

One day, I heard “right on the money.” I thought that would be a good way to clue a turning puzzle, which is where answers from the puzzle turn between multiple answers. I let it stew for about a year. 

Getting a puzzle accepted in The New York Times is quite challenging, and this type of turning genre is one of those tried-and-true genres. The burden to get one published is quite higher because they want something new or a little different. So I spent a lot of time thinking about how I could make the puzzle particularly refined

How do you balance this with being a student?

I think crossword puzzles are almost an ideal hobby for me because I genuinely find it incredibly fun. In the same way that playing video games might be fun or playing your favorite sport might be fun, crossword puzzles are that equivalent to me.

What’s the reaction of your classmates or professors?

I don’t think any of my professors know about it. I enjoy that. I like having my little secret life. 

It was quite funny a couple of weeks ago, in one of my classes, someone walked up to me and said they solved my crossword puzzle. 

I also have made quite a few friends through crossword puzzles. On campus, The Chicago Maroon [newspaper] has their own crossword section. So I’ve been able to meet other people who are interested in constructing there.

I’ve also been able to meet other people who really like solving puzzles and who kind of already knew that I existed just by virtue of, keeping up with who gets puzzles published in The New York Times. And some of them have ended up being some of my best friends because turns out people that love crosswords tend to have quite a lot of other things in common.

Is this something you hope to do more in the future?

If I got a stable crossword editing position, it would be hard for me to turn that down. I even more so view crosswords as a lifelong hobby and something that I will enjoy doing when I’m 80, hopefully even older than 80.

All you need to write a crossword puzzle is a computer or, if I have enough time, a pencil and paper. So whether I’m on a plane, in Chicago or anywhere around the world that has Wi-Fi, I’ll be able to write a crossword puzzle. And that’s very cool.