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He has the answers

Crossword-puzzle designer looks across the road and down the street for new clues

Hey there, time traveller!
This article was published 17/2/2018 (903 days ago), so information in it may no longer be current.

A certain leader of the free world might dismiss the following as "fake news," but Derek Bowman, a crossword-puzzle designer whose brain teasers have been published worldwide says there’s a simple explanation why the 44th president of the United States’ surname shows up in more crosswords than that of his successor.

"It’s not as if all puzzle-writers are Democrats," Bowman says, seated in the living room of his Osborne Village condominium where myriad dictionaries and encyclopedia — his tools of the trade — are stacked on an otherwise spotless coffee table. "It’s just that five-letter names like Obama, which go vowel-consonant-vowel-consonant-vowel, are much easier to incorporate into puzzles than something like Trump is."

Bowman, a "big-time" tennis fan, points out that’s one of the reasons he was rooting for No.4-ranked Elina Svitolina to net the women’s title, at the 2018 Australian Open.

"I like Elina just fine, already," he goes on, "but if she starts winning grand slams, I’ll like her even more because then I’ll be able to use her (first) name in my crosswords."

<p>Derek Bowman, crossword puzzle designer.</p>


Derek Bowman, crossword puzzle designer.

Bowman guesses he was seven years old when he began making weekly trips to a convenience store down the street from his childhood home in Waverley Heights, to spend his allowance on fill-in puzzle books — fill-in puzzles being the type you solve by fitting specific words into a crossword-style configuration. As he got older, he moved on to bona fide, clue-driven crosswords. Every now and then, though, he’d fetch out his old fill-in books — not to complete puzzles he never got around to, but instead to fashion his own crossword puzzles on pages left blank.

"I’d come up with different words for the empty spaces then write clues for them. When I was all done, I’d give them to my dad to solve," he says.

By the time Bowman enrolled at the University of Manitoba in 1999, he was creating multi-row-and-column crossword puzzles entirely from scratch. During his second year of studies, he submitted a few to The Manitoban. He was over the moon, he says, when somebody from the student-run gazette got back to him, saying he could expect to see them in print in the near future.

"It was pretty cool, walking around campus and, every once in a while, spotting somebody working on my puzzles," he says. "But probably the most important thing that happened during my time there was meeting another student, Craig Kaspar, who also writes crosswords. After seeing my puzzles in The Manitoban, he sat down with me and kind of refined what I’d been doing, and told me about different resources I could utilize. He definitely helped me start getting published in other places like Uptown."

<p>Crossword puzzle designer Derek Bowman's puzzles have appeared in publications such as the New York Times and the Wall Street Journal.</p>


Crossword puzzle designer Derek Bowman's puzzles have appeared in publications such as the New York Times and the Wall Street Journal.

After graduating with an arts degree in sociology, Bowman began submitting his puzzles to the New York Times, whose daily head-scratchers are syndicated by more than 300 newspapers, including the Winnipeg Free Press. Sure, he was on the receiving end of dozens of email messages that began "interesting puzzle but..." He says he never got discouraged.

"Sometimes they’d say I used too many three-letter words, or they’d mention they weren’t too crazy about the theme I’d chosen. But they always gave me suggestions, which I tried to put to good use, the next time."

In 2009, Bowman was checking his email when he spotted a message from one of his regular contacts at the Times. He got a shiver down his spine when he scanned the subject line, which, instead of reading "crossword" as it usually did, read "crossword - yes!" On Aug. 29, 2009, following seven years of trying, Bowman and his family went out for drinks, to celebrate the appearance of the first Bowman-penned puzzle in the pages of the Old Gray Lady. (His claim to fame: his NYT-debut marked the first time anybody had used OMG as an answer in that publication. "Online gasp," he responds with a grin, when asked what his clue was.)

To date, Bowman’s crosswords have been published in the Times eight times and in the Los Angeles Times on six occasions. He has another puzzle slated to run in the latter paper in March, but because it’s verboten to discuss clues or answers ahead of time, all he can reveal is it’s supposed to appear on a Tuesday — a day that presented a problem for one of the words he had originally hoped to include. (Like the New York Times, puzzles in the L.A. Times get progressively tougher as the week goes on.)

"I really wanted to use GZA, who’s one of the guys in the Wu-Tang Clan, but the editor said, ‘You are not putting a member of the Wu-Tang Clan in a Tuesday-level puzzle,’" Bowman says. "I was like, ‘GZA is the only thing that fits,’ but he still said no dice. So I had to rip that section of the puzzle apart and start over."

MIKAELA MACKENZIE / WINNIPEG FREE PRESS</p><p>Derek Bowman, crossword puzzle designer.</p>


Derek Bowman, crossword puzzle designer.

Because the 38-year-old never knows when inspiration is going to strike, he keeps a pencil and notebook handy at all times. One morning, on the way to his full-time job at Winnipeg Public Library’s Sir William Stephenson branch, he spent the bulk of his bus trip debating whether his prompt for the letters I-S-H-O-T should be "strike while the iron ___ " or " _____ the Sheriff, Eric Clapton tune."

"If puzzling was just grid design — fitting the words on the page and sussing out where the black squares should be — I could literally go all day, I love it so much. But cluing has always been a tough slog for me. Not only do you have to be 100 per cent accurate, you have to try and make it a fun ‘get.’ And for certain words, like pilaf, there are only so many ways to clue them: rice dish, seasoned rice dish, side dish..."

As for remuneration, Bowman says the New York Times pays contributors US$300 per puzzle, a stipend that jumps to US$360 once you’ve been published 10 times. He chuckles when asked what that amounts to, per hour.

"Ha, I don’t even want to think what my hourly wage would be. Let’s just say for the amount of time it takes me to make a puzzle, start to finish, I’m lucky if I’m making minimum wage."

Bowman recently launched a sideline venture, crafting custom-made crosswords for people on the hunt for a unique gift for a loved one. Before getting down to business, he hooks up with interested parties for coffee or a bite to eat, at which time he peppers them for information about the puzzle’s intended target.

<p>Derek Bowman's scribbles.</p>


Derek Bowman's scribbles.

Last summer, Pierre Campeau was trying to figure out what to get his wife Doris for their 30th wedding anniversary. After hearing about Bowman’s biz, the two arranged to meet at Stella’s on Pembina Highway. Toward the end of their encounter, their server couldn’t help but ask them what was going on, exactly.

"She said she wasn’t trying to eavesdrop, but that we’d been sitting there for 90 minutes talking about everything under the sun, while Derek kept jotting things down," Campeau says. "When I told her he was making a crossword puzzle for my wife for our anniversary, her eyes practically welled up. She said that was the most romantic thing she’d ever heard of."

On the night of their anniversary, the Campeaus went out for dinner. When their waiter arrived with dessert, he also presented Doris with the crossword Bowman came up with. Before long, she was remarking "That’s odd; the answer to 58 Across is the name of my school," and "Hey — the answer to 135 Across is one of our son’s names."

"Neither one of us is what you’d describe as crossword people but that night, she must have stayed up till midnight, finishing her puzzle," Campeau says. "I tell people Derek is one of Winnipeg’s best-kept secrets. I mean, the guy’s a genius."

Finally, because this reporter’s wife is somewhat territorial when it comes to solving her daily crossword ("If I need your help I’ll ask," is a common refrain in our home) we wondered how Bowman feels about people glancing over his shoulder when he’s trying to come with the answer to, say, 10 Down, or 32 Across?

"Oh, that doesn’t bother me at all, I’m pretty communal with puzzles," he replies. "Because the creating side-of-things is such a solitary endeavour, whenever there’s an opportunity to involve somebody else in the solving aspect of it, I’m all for it."

On Feb. 24, Bowman will host Crazy for Crosswords, a free, two-hour program during which he will talk about the history of crossword puzzles, as well as give tips how to solve and design puzzles. The drop-in event will be held at Sir William Stephenson Library, 765 Keewatin St. Also, if you’re interested in a personal crossword puzzle, you can get in touch with Bowman at

<p>The day Derek Bowman received an email saying his crossword puzzle was accepted by the New York Times was a memorable one.</p>


The day Derek Bowman received an email saying his crossword puzzle was accepted by the New York Times was a memorable one.

David Sanderson

Dave Sanderson was born in Regina but please, don’t hold that against him.

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