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Far from clue-less, CDN crossword creator Matt Jones has made his mark

Bonus words: NYT puzzle guru Will Shortz fills in the blanks of crossword history

Matt Jones creates "Jonesin' Crosswords
Matt Jones creates "Jonesin' Crosswords
By Jaya Flanary Digital Editor/Designer

Editors note: CDN’s digital editor, Jaya Flanary, says her biggest initial mistake designing pages for the print edition was placing the crossword clues next to Matt Jones’ crossword puzzle, rather than wrapping them around it. Longtime readers knew it should be formatted to fit in a single quarter of our broadsheet page, folded into a tidy package. She not only regrets the error, but offers the following as an apology. 

Matt Jones works from home doing customer service for a chain of hospitals’ billing departments. But once a week, he sits down and, rather than solving crosswords like the average puzzle lover, creates one. 

“I have to have another job,” the designer of the crossword appearing weekly in CDN said with a laugh. “I have a friend of mine who said he could count the number of people who have this as a full-time gig on one hand, maybe, and those people are kind of disappearing, too.”

Originally from a small town outside Portland, Jones, 47, now lives in Gladstone, Oregon, where he creates a weekly crossword published in nearly 25 publications across the United States, primarily on the West Coast.

Jones initially began crosswording at age 10 when his teacher introduced him to Games magazine. After subscribing, Jones started timing himself solving puzzles, researching tournaments and learning about how to create crosswords.

photo  Matt Jones completes a crossword puzzle for a photoshoot during his senior year of high school. (Photo courtesy of Matt Jones)  

In 1994, during Jones’ first year in college, he got a puzzle printed by The New York Times. In the late ’90s, he was awarded “second place in juniors, or something” in a tournament. 

The internet was starting to catch on and Jones was meeting other puzzle fanatics online. His first paid gig was when he joined a syndicate with a dozen people who wrote a daily crossword together.

Soon after, Jones was approached by Matt Gaffney, a “big name” in the business who wanted to break into a new market: alternative newsweeklies. At the time, most alt-weeklies were running syndicated crosswords from mainstream papers like The New York Times and Los Angeles Times.

“[Gaffney] wanted to find something that had a little bit more of the voice and the attitude of an alternative newsweekly,” Jones said. “That’s when he found what I was doing and it just kind of clicked together.”


Gaffney became Jones’ editor, and sort of his agent. “Jonesin’ Crosswords” launched in May 2001. That same year, Jones won the B division at the 24th annual American Crossword Puzzle Tournament

In 2019, Gaffney handed the reins to Jones entirely.

According to Jones’ resume, Jonesin’ Crosswords reached the 1,000-puzzle mark in 2020.

photo  Matt Jones, second from left, at the 24th annual American Crossword Puzzle Tournament in Stamford, Connecticut, in 2001. Jones won the B division, while Ellen Ripstein, right, won the A division. (Photo by Donald Christensen, courtesy of American Crossword Puzzle Tournament)  

Crossword [9-letter word for Darwin’s big idea]

As Jones’ work matured, the crossword ground was changing beneath him. Both the creation of crosswords and how they are solved have evolved dramatically since the first puzzle was published in 1913.

The 1970s, Jones said, was the last era that crossword answers had to be in the dictionary or reference books. In the 1980s, a “New Wave” began, and those “musty” crosswords, Jones said, were no longer.

photo  Will Shortz has been editing The New York Times crossword for 30 years. (Photo courtesy of Will Shortz)  

Will Shortz, who celebrated his 30th year as the crossword editor of The New York Times in November 2023, told Cascadia Daily News that the ’80s brought playfulness, wordplay and modern clues to crosswording — plus, younger contributors, like Jones, were rising to the surface.

Shortz, 71, is the Times’ fourth crossword editor and the nation’s acknowledged master (scroll to bottom for solving tips from Shortz). He took over the job in 1993, the same year the World Wide Web launched into the public domain. Meanwhile, Jones, almost a college freshman, was just one year away from getting his puzzle printed in the Times.

The ’90s brought complete transformation. Before computer-assisted programs, people like Jones made crosswords by hand on graph paper. Now, he uses a specialty software called Crossword Compiler, one of three programs used by most creators.

“Crosswords have never been as good as they are today,” Shortz said. “We’re living in the golden age of crosswords.”

Shortz is clear and concise about why: Software allows people to make better puzzles with more interesting words, vocabulary and themes; the internet helps puzzle makers write more interesting clues; and crossword blogs provide space for feedback, which ideally helps people like Jones improve their work.

photo  Will Shortz, left, and Ellen Ripstein speak at the American Crossword Puzzle Tournament in 2001. Ripstein was the tournament champion that year. (Photo by Donald Christensen, courtesy of American Crossword Puzzle Tournament)  

Crosswords are now regularly enjoyed on smartphone applications that time the user and notify them when the wrong answer is submitted. 

But Jones doesn’t believe the very newest technology, artificial intelligence (AI), will automate the craft. 

“The answer to that is almost across the board, absolutely not,” Jones said. “You can go into ChatGPT right now and say, ‘Hey ChatGPT, will you try to write me a theme?’ and it will stumble out of the gate and fail spectacularly — and tell you step by step how well it’s doing.”

(Author’s Note: You can, in fact, ask ChatGPT to write crossword clues. I know because I used it to write this story’s subheads. Just for fun.) 

Shortz concurs.

“AI has come so far, in just the last few years, it’s really hard to predict,” Shortz said. “But AI is not going to take over crossword jobs anytime soon. Because it’s very hard to make a quality crossword, and only a human knows what an interesting answer is.”

Similar to how AI can write a joke — a “lame” one, Shortz said, not a funny one — AI could probably do Jones’ side gig, but poorly.

photo  Folks flip through newspapers in the hotel lobby at the 2001 American Crossword Puzzle Tournament. (Photo by Donald Christensen, courtesy of American Crossword Puzzle Tournament)  

[8-letter word for giving something life] crosswords

Jones’ creation process is typical: It’s the complete opposite of solving. While puzzle solvers read clues, fill in answers and then figure out the theme, puzzle makers choose the theme, place the answers and then write the clues.

“Most of the time, I will try to think of a theme that has a weird, punny answer,” Jones said. “The inspiration can come from just about anywhere.”

A trivia lover and “voracious consumer of pop culture” who watches more TV than movies, Jones said he has applied for “Jeopardy” five times.

“They have not called me,” he said. “I’m just crossing my fingers.”

photo  Awards sit on a table during the 24th annual American Crossword Puzzle Tournament, where Matt Jones won the B division. (Photo by Donald Christensen, courtesy of American Crossword Puzzle Tournament)  

Though his distribution is widespread, Jones doesn’t receive much feedback for his 15-by-15 grids other than critiques from “Diary of a Crossword Fiend,” a weekly blog that reviews and rates puzzles.

The most common critique from solvers is that Jones’ puzzles have too many pop culture references. But he doesn’t plan to change tactics.

“I want to make it for everybody,” Jones said. “I don’t want to sell out.”

The puzzling [6-letter word for what a butterfly’s wings can have]

Shortz and other creators believe the craft, intentionally or not, has come to have a higher purpose.

“Crosswords genuinely expand your knowledge and expand your vocabulary,” he said. “They literally make you a better person.”

Cascadia Daily News readers agree: Solving crosswords is just good for you. While some solve one a day or one a week, one reader in his 80s does three a day and six on Sundays. Some of Jones’ Bellingham fans predate CDN; his puzzles appeared in a predecessor publication, Cascadia Weekly, “as far back as 2007,” Jones said.

photo  Matt Jones has published two crossword books, one in 2004 and “Jonesin’ for Crosswords” in 2009. (Photo by Howard Lao)  

One of the younger avid Bellingham crossworders is 20-year-old Kaitlyn Schroeder, a Western Washington University student who chooses paper crosswords to limit her screen time. Schroeder, who does one in the morning to wake up and one at night to relax, finds crosswords to be a good conversation starter with older generations. 

Carol Brach, 76, who solves one crossword puzzle daily, said her mother was a “crossword freak,” and she remembers laying out the newspaper with her five siblings to solve puzzles together. 

“My father was an immigrant and English was not his first language,” Brach said. “My mom was an English major and a stickler. So [my father] always wanted to learn more and he did.”

Rick Lowell, who regularly solves The New York Times, Los Angeles Times and Wall Street Journal crosswords every Sunday, completed his first Jonesin’ crossword on Dec. 1, 2023.

“I was blown away because there’s a gross error,” Lowell said.

Lowell, 67, explained that the answer “USAF” to the 53 across clue “‘Top Gun’ org.” was wrong because the “Top Gun” organization is the U.S. Navy, not U.S. Air Force. Lowell is not only former Navy, but also has watched all the “Top Gun” movies.

photo  Cascadia Daily News reader Rick Lowell noticed an error in Matt Jones’ crossword in December 2023. Lowell circled the clue and wrote “NO!” in the margin. (Photo courtesy of Rick Lowell)  

A self-proclaimed “crossword puzzle aficionado, but no expert,” Lowell chose to keep trying Jones’ crosswords in CDN despite the error.

All readers agreed on one general strategy: If you’re stuck, leave it alone and come back to it the next day.

“It’s amazing how often that trick works,” Shortz said. “It’s like you see one little thing that you didn’t see before and you’re off and running again.”

As for the future of crosswording? Shortz said it’s too hard to predict. But he does know one thing.

“Crosswords have proven to be unusually resilient,” he said. “Crosswords have jumped to the digital age. They work on paper, but they also work great on your laptop or your telephone. Crosswords have kept modern.”

Solving tips from Will Shortz

Are you bad at solving crosswords? Here is some advice from the expert himself:

• Start with The New York Times’ Monday puzzle, as it’s the easiest of the week. Build up from there.

• Fill in what you know for sure. Build out from there.

• Don’t be afraid to erase. Sometimes you make mistakes. (FYI: Shortz uses an erasable pen when solving crosswords!)

• If you get stuck, put the puzzle aside and return to it later.

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