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These 2 St. Louisans Are Bringing New Life To Crossword Puzzles

Matthew Stock (at left) and Sid Sivakumar (at right) are St. Louisans dedicated to puzzle making and are frequent collaborators.
Matthew Stock | Sid Sivakumar
Matthew Stock (left) and Sid Sivakumar are St. Louisans dedicated to puzzle making and are frequent collaborators.

The puzzle industry is changing. More crosswords now cater to younger, more diverse audiences. That means fewer references to 1950s movie stars and more nods to modern celebrities and cultures other than white America.

For that, you can thank the rising generation of puzzle makers, which includes St. Louis residents Sid Sivakumar and Matthew Stock. Both are in their mid-20s and are making strides in the industry: They each have their own puzzle website and have seen puzzles published in publications such as USA Today. Last week, a puzzle they co-wrote was published in the New York Times. It was Stock’s Times debut and the sixth puzzle to be placed there by Sivakumar.

The two became friends in 2019 after joining a Facebook group meant for new puzzle constructors, particularly those from underrepresented backgrounds. Once they found out they lived in the same city, they met at Pieces Board Games in Soulard and worked on crossword puzzles for hours. Now they are frequent collaborators.

Matthew Stock made his New York Times Crossword debut in a collaboration with Sid Sivakumar on Jan. 7, 2021.
Matthew Stock
Matthew Stock made his New York Times Crossword debut in a collaboration with Sid Sivakumar on Jan. 7, 2021.

“We've learned a lot from each other,” Sivakumar explained on St. Louis on the Air. “Matthew has a complementary skill set to the one that I have. We've learned to sort of blend our skill sets as we build more puzzles together.”

Sivakumar has long been obsessed with the puzzle’s grid, while Stock focuses on making the clues just right.

“I always love to bring things that will make people smile to a puzzle,” Stock explained. “If I can get somebody to smile or laugh or grin a little bit while solving a puzzle, then I think I've succeeded as a puzzle maker.”

Their themes run the gamut. But both are intent in bringing new communities to what Stock refers to as the “puzzleverse.”

“As the puzzles become more popular and are solved by more people, I think this idea of, ‘Who is solving my puzzle?’ becomes more and more amorphous or unclear,” he said. “And for me, I like to make puzzles that I would enjoy solving myself, as a young person who enjoys learning new things about different cultures.”

Sivakumar, who is of South Asian descent, added that he sometimes felt excluded by puzzles aimed solely at older white audiences.

“My journey to crosswords was actually a reckoning with things in the New York Times that I felt were outside of my wheelhouse,” he said. “And at first it felt like I was not good enough to solve puzzles, like I didn't have the same lexicon, like I didn't have the same knowledge base, and therefore I was lesser.”

As he developed his skills, Sivakumar said he came to a realization: “The people that are editing and writing crosswords … simply [don’t] share the same experiences that I do.”

That’s driven some of his choices in puzzle construction.

“I want people who look like me and sound like me and talk like me and eat like me to be solving puzzles, too,” he said. “Because largely, if they encounter a white actor from the 1950s, or yet another golfer or another baseball reference, they might be much less likely to get into this brilliant and beautiful hobby with a vibrant community.”

Stock sees that first-hand. A ninth grade algebra teacher as part of an AmeriCorps program in East St. Louis, he recalled how ecstatic his students were, pre-pandemic, solving the puzzles in the New York Times mini page-a-day calendar on his desk. That led to him helping them create puzzles during their lunch break.

“It was a really wonderful thing to see them taking to this thing that they may not have seen other people in their world doing the puzzle regularly, the way that I grew up with the New York Times puzzle,” he said.

As for Sivakumar, he is a medical student pursuing a double doctorate at Washington University in St. Louis. Constructing puzzles helps exercise his brain in a different way than his studies provide.

“It actually helps me stay more focused on my work, because [when] you do a puzzle for about five or 10 minutes, you're subscribing to the universe that the constructor and the editor have created for you,” he said. “You're substituting the reality around you for what's in that grid.

“And there's always a solution,” he continued. “In medicine, and in science, especially, there's not always a solution. And that is sometimes deeply troubling from an emotional perspective. So to be able to do a puzzle, either to make one or to solve one, and then have that solution stare you in the face and say, ‘I did this and it's complete,’ I can tie it up a neat little bow and say, ‘I've finished.’ It gives me a lot of motivation to continue doing my other work.”

Check out their work online via their websites: Sid’s Grids and Happy Little Puzzles.

St. Louis on the Air” brings you the stories of St. Louis and the people who live, work and create in our region. The show is hosted by Sarah Fenske and produced by Alex Heuer, Emily Woodbury, Evie Hemphill and Lara Hamdan. The audio engineer is Aaron Doerr.

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