Toronto wordsmith Fraser Simpson has been creating the weekly cryptic crossword for The Globe and Mail for twenty years, making him the longest-running Canadian constructor whose work appears nationwide. He has published several books of puzzles (both cryptic crosswords and other types) and has had several cryptics published in The New York Times. Simpson was also the editor for The New Yorker’s all-too-brief two-year experiment with cryptics. For this blog post, he answered some of our questions about his career and about cryptic crosswords in general.

How did you first get interested in cryptics? Was it a separate step from discovering puzzles in general?

I had always been interested in solving and creating puzzles as a child. I went to boarding school as a teenager, and before one three-hour train ride home for a holiday, I purchased at the train station bookshop a volume by Barry O. Higgs titled The New York Times Guide to Solving Cryptics, Crosswords & Anagrams. I was mesmerized as I worked through the book on the train ride, and the next day started a routine of solving the daily syndicated cryptic in The Globe and Mail. It didn’t take long before I was creating my own puzzles for family and friends. Many years later, in 1994, I became the new Saturday cryptic author for The Globe and Mail.

When we talk about the cultural differences in cryptic crosswords and in the world of crosswords generally, we mostly wind up talking about the US versus the UK. Where does Canada fit into that division? Is it closely aligned with one side or the other, or does Canada have its own hybrid puzzle culture?

I solve a lot of British crosswords, so I think that my style has been somewhat influenced by that side of the Atlantic, especially in the puzzles I create for my Canadian audience. But the great constructors of the United States have influenced me a lot more, especially when I was in my 20s and early 30s, and that is apparent in my clue-writing style.

You were at the helm of one of the more visible outbreaks of cryptic puzzling in the US, when The New Yorker began running a small cryptic every week in 1997—and then abruptly shut it down after a short run. How did that come about?

The project started out as an idea thought up in the early 1990s by Will Shortz, and he asked me to team up with him to co-edit. It was originally supposed to be a weekly full-on variety cryptic (imagine that!), but because of space limitations, The New Yorker suggested a single column. Unsure that this would even work, Will phoned me and said that perhaps the project was dead, but I told him that I would try to make a smaller puzzle that would fit that space. I created the 8 x 10 grid after measuring the magazine’s columns, and sent a sample puzzle to Will. He liked it and agreed we could go forward with this size, as unusual as it was.

When the puzzle finally started running, the unusual size turned out to be a gem, and the puzzles I got from my regular stable of constructors were delightful. In 1998, The New Yorker changed editors from Tina Brown to the current editor David Remnick, and The New Yorker underwent some changes, one of which was the discontinuation of the little cryptic crossword. We were all sad to see it go, and I still sometimes wonder what would have happened if we had been allotted two columns instead of one!

Can you describe your philosophy or approach to cryptics? What do you consider most important, as a constructor and/or a solver?

I am much more strict as a constructor than I am as a solver. I prefer not to have any extra words, including connector words, in clues I write, and based on the feedback from my regular solvers, they really like this feature of my work. Strangely, though, I do not feel the same way as a solver. I find that when I solve some British cryptics, their slightly looser style makes the solving more challenging, which I enjoy. I am more easily fooled by their extra words, as these extra words increase the number of possibilities of what might actually be going on.

We have the impression that you used to be very strict adherent to the principles outlined by the British constructor Ximenes (no connectors, etc.) but that your position has softened over the years. Is that true, and if so why and how?

I don’t think I’ve softened at all on this! But I do think my clueing style has changed over the years, and that I write much harder clues than I used to. I try to keep the number of anagrams in my puzzles to six or fewer, if I can. Sometimes I have so few anagrams that I have to go back and change clues to introduce more of them!

Like Henri, you’re a math teacher by profession. Do you feel a connection between your interests in math and in puzzles?

I feel that my whole life revolves around puzzles. A lot of mathematics feels puzzle-based to me, with some of the same payoffs provided by a good puzzle. I taught my tenth graders today how to prove trig identities, and one young woman exclaimed while doing some of the assigned exercises, “It’s so satisfying when it all works out!” She could have been talking about a cryptic clue instead of a math problem.

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