A crossword creator who likes playing with words

By Sue Baldani

Doing crossword puzzles is a great way to stimulate brain health, learn new words and have fun. But, do you ever wonder who actually creates these interesting grids?

While many people think they’re computer generated, that’s not the case. Although computers can assist, it takes a skilled person to develop the actual puzzles.

“I’ve been solving crossword puzzles my whole life, but I never thought about who made them,” said Gainesville, Virginia resident, John Kugelman. “I never paid attention to the names on the puzzles, the authors. I guess I just assumed they were computer made.”

When he realized that wasn’t true, he decided to try his hand at creating one of his own. The first one was for his father, a huge crossword puzzle fan, about 10 years ago, but he didn’t actually start creating them on a regular basis until 2022.

Today, his crosswords routinely show up in the New York Times (NYT), the pinnacle of the crossword puzzle world. Even more impressive, he had the most Sunday puzzles published last year, which are larger and more complicated than the rest of the week.

“I currently have had nine published and another seven have been accepted,” he said.

A software developer by day, he has been focused on cyber security for 20 years, and has even worked on submarine defense. Now, in addition to his full-time career, he works on puzzles every night.

So, how do these crosswords actually come together? “There are two different kinds of puzzles – themed and themeless. I like doing themed ones, so for me it always starts with trying to come up with a kind of wordplay. I then jot down a lot of examples because you usually need about half a dozen examples to make a puzzle out of them.”

He related it to telling the same joke over and over again, just in a different way.  “The last puzzle I did was taking the word ‘wheel,’ but starting it off with ‘sq.’ So, wheel of fortune became squeal of fortune. The Great Wall of China turned into the Great Squall of China. I then found ways to clue it.”

That, explained Kugelman, is step one. Step two is building the grid itself and making the words all come together. This is where computer software can help. “It doesn’t do it for you, but it helps to show you the different words that can fit in the letter patterns needed. But, even when you have the software, using it is pretty difficult. You still have to figure out where to put the black squares and where to put the answers. It doesn’t just arrange it for you.”

He is always coming up with ideas, and records them in notebooks, scraps of paper, and on his phone. “I have notes everywhere that you can take notes.”

Just like writers, puzzlers have their own styles. Puzzles can have very visual elements, and Kugelman recalled one in the NYT where the black squares looked like hot air balloons and the answers involved hot air balloon language.

“It was very cool, but that’s not my style,” Kugelman said. “Mine are wordplay heavy. I usually start with some kind of pun or a ‘dad joke’ type of thing. My editor, Will Shortz, likes consistency and wants me to stick to what he’s expecting from me.”

Will Shortz, he explained, is the lead crossword editor at the New York Times and has been there since the mid-90s. “He’s the guy. If there’s anybody in the crossword world that’s famous, it’s him. He’s also on NPR every week and does their puzzle segments.”

Since 2022, Kugelman has created over 50 puzzles, and in addition to having some of them published in the NYT, they’ve also been published in other newspapers. “I have one coming up in the L.A. Times, and then Universal is a syndication thing, so they end up in hundreds of different newspapers. That has been cool because they show up in the Prince William Times and the Fauquier Times, so I can see them in local papers.”

Kugelman, who lives with his two feline roommates, Ginger and Pepper, has always loved putting words together, and before doing crossword puzzles, he wrote song lyrics. He also plays the guitar and a little piano.

“Composing was the main thing I liked doing, but once I tapped into crosswords, I took that same creative energy and put it in a different place.”

He finds creating crossword puzzles very satisfying. “It seems to scratch the same itch, but now I actually get paid for it,” he said.

Written for Haymarket & Gainesville Lifestyle magazine in Virginia.