2019: The Year In Crosswords

T Campbell
9 min readJan 1, 2020
Anna Shechtman illo, via The Daily Beast

Both the progressive and the traditional arms of the crossworld saw serious growth this year — enough so that there was serious talk about a new golden age of crosswords. The Inkubator launched early this year, producing thirty puzzles by women — cis women, trans women, and women-aligned constructors. Queer Qrosswords returned with a sequel to its original themed collection. New York and Vox joined the ranks of popular websites with crossword features (although Vox has already drawn some of the wrong kind of attention for some distinctly macabre cluing). The New Yorker expanded its offerings, introducing a new “weekend crossword” and bringing its late-twentieth-century cryptic crosswords back for the online market.

Tne New York Times

One reason for the influx of crossword features online is that the New York Times continues to do well, with its online crossword and otherwise. The Times has even invested a little advertising in the crossword in noted hipster centers Boston and Seattle, and has a retrospective on its mini-crossword feature. Will Shortz announced a change in constructor pay that’s a bit complex to summarize but will benefit regulars.

The NYT also rolled out two additional puzzles this year to accompany the crossword and last year’s addition of the spelling bee. One, Letter Boxes, will appeal to word nerds, and the other, Tiles, is, a bit curiously, a freebie aimed at the non-native-English-speaking market.

Crowdfunding

Eric Berlin published his simple-but-unusual Puzzlesnacks, funded on Kickstarter in 24 hours. Similarly funded was Mike Selinker and Pete Venters’s Maze of Games and Peter Gordon’s Fireball Crosswords 2020. Also successful on a much more modest level was David Millar, whose $100 goal for a single number-cross puzzle succeeded with $109. (As promised, Millar included the number of funding dollars within the grid. In his proposal, he noted, “If the campaign raises $100,000,000,000 or more, I will have to increase the size of the puzzle grid, but I am prepared to tackle this scenario should it arise.”)

The Indiest of the Indie

More specialized new fare included Trent H. Evans’ series with a slant toward mental health issues, Grid Therapy, as well as the build-your-own-Boggle-type game Ten Words, new features in Latin and Yiddish, and crosswords about spying and various nerd obsessions — “for geeks, techies, gamers, and otakus alike.” Sid Sivakumar and Ross Trudeau also launched indie puzzle blogs. Trudeau had a particularly interesting essay on crossword inclusivity, occasioned by response to his NYT puzzle.

Congratulations to our New Hires

David Steinberg graduated college and settled into Kansas City, taking on and firming up his position as Andrews McMeel Universal’s puzzle editor. He’s taking submissions for both crosswords and alternative kinds of puzzles. AMU also promoted Erik Agard (also of The New Yorker and other accomplishments) to USA Today puzzle editor.

Also, Andy Kravis (profiled below) joined the NYT crossword editing and correspondence team with Sam Ezersky, Joel Fagliano, and Will Shortz.

Departures

For all the gains the crossword marketplace made this year, there was one major loss: the puzzle for The Chronicle of Higher Education. Though this page makes it appear that the puzzle is only moving to print, editor Brad Wilber confirms that it will disappear there too in February 2020. The Chronicle puzzle was a consistent pleasure for those seeking a little more scholarly emphasis in their puzzle themes, and a favorite of reviewers, as well. It will be missed, but Wilber is to be congratulated on its healthy run.

Crossword Tech

One side effect of the yen for online crosswords is that it’s helped develop software that promotes the solving experience. Here’s a somewhat advertorial piece about PuzzleMe, the solving platform for The New Yorker, Newsday, and The Washington Post, among others.

A couple of new softwares emerged for the aspiring constructor on a budget, Crossword.Tools and Sparkling Fill. I haven’t really had the time to test either, but initial buzz seems promising. XWordInfo also refined its features to be more mobile-friendly and faster. The biggest help to constructors in 2019, though, was the continued development of collaboration and mentorship.

Will Shortz

Shortz’s side projects this year included a “How I Work” article for Lifehacker.

Shortz and Fred Piscop worked with the Alzheimer’s Foundation of America and the families of real-life victims to construct “The Hardest Crossword,” a frightening journey into the life and mind of an Alzheimer’s sufferer. The puzzle may seem at first glance to be solvable with a few guesses. Then one looks closer. “Only one person knows all the answers. But she doesn’t remember them anymore.”

He also remained involved with the continued production of Hallmark’s Crossword Mysteries, soon to release its third installment.

Controversies of the Year

Shortz making time for extracurriculars doesn’t mean the NYT crossword has had nothing but clear sailing in 2019, though. The most prominent institution is usually the most criticized, but Shortz and his team brought some extra heat onto themselves with the answer BEANER, clued as “Pitch to the head, informally” but better known as a slur against Mexicans. There was also a relatively minor social-media kerfluffle when the NYT’s social media department engaged — perhaps a bit too much — with a user who joked that the fastest crossword solver would get to execute a pundit of their choice.

On a lighter subject, who’s got the best Cuban sandwiches, NYT: Tampa or Miami?

While the NYT stumbled into these controversies more or less unintentionally, it’s pretty likely the Guardian crossword setter known as “Philistine” knew exactly what he was doing when he hid “BOLLOCKS TO BREXIT” in the edges of one of his puzzles.

Solver Stories

The latest club of devoted crossfans? US Men’s National Soccer. They’re just following in British players’ footsteps.

As these memoirs attest, crosswords can be a ritual of sisterly bonding or mother-son bonding or intergenerational bonding, a cure for “mommy brain,” and a healthy balm for trauma and anxiety.

And every once in a while, they can help your business, especially if you’re a cat cafe.

Crossword Tournament News

Dan Feyer is now the American Crossword Puzzle Tournament’s winningest participant. More surprisingly, a scoring error denied the tournament’s B division a chance to hash things out by going to the big boards, as seen in the video of Feyer’s win below, so winners were taken from the best performers in solving the first seven puzzles.

Nothing else particularly noteworthy here (a lot of tournaments report on their upcoming schedules, but not on their winners). But see also “Crossword Proposals”…

Crossword Lotto Winners

Roberto Garcia-Barrera of San Diego was likely the biggest such winner of the year, and his $2 million prize prompted a vacation and some serious reflection before he claimed it.

Other winners included Ivan Camacho/Comocho (spelling uncertain) at San Juan ($750K), Vicky Brymer of Jacksonville ($500K), someone in Schofield, Wisconsin ($500K), Dennis McKnight of Sullivan, Wisconsin ($500K), Patricia Inman of Des Moines ($300K), Damon Cherico and Shayna Flanders of Brick Township, New Jersey ($250K), and Diane Pomerleau of Windsor Ontario (CAN$250K).

Crosswords in Other Media

Zach Sherwin, whose other credits include songwriting for Crazy Ex-Girlfriend and Epic Rap Battles of History, has developed The Crossword Show, a live comedy routine that combines crossword-solving and hip-hop lyrics.

And here’s the lyric video for Lambchop’s sad, somewhat abstractified “Crosswords, or What This Says About You.”

Constructor Profiles

The most prominent constructor of the year is Anna Shechtman of The New Yorker who along with Erik Agard may have gotten more screen time than Will Shortz this year, thanks to The New Yorker’s many intriguing videos on the subject of crosswords (sample below, but more examples here).

Also notable was Natasha Lyonne, who translated the success of her TV hit Russian Doll into a crossword publication at the NYT (in partnership with Wordplay mainstay Deb Amlen) and shared a little stand-up on the subject.

Other constructors profiled: Manny Nosowsky, Emily Cox and Henry Rathvon, Damon Gulczynski, Andrew Ries, Andy Kravis, Emily Carroll, Ryan McCarty, Andrew Kingsley, Joon Pahk, John Henderson, Tracy Bennett, Finn Vigeland, Wren Schultz, Ruth Bloomfield Margolin, Jack Mowat, Ellis Hay, and Michael Whyte.

Crossword-Adjacent News

Dinner-hour puzzlemasters Pat Sajak and Alex Trebek both had medical troubles this year, with Trebek’s diagnosis the more serious of the two and Sajak briefly passing the reins to Vanna White. But both are still in the game. Some aspects of Wheel of Fortune’s game, however, might be due for a change; a bit of grammatical hair-splitting cost one November contestant her victory.

As a local publication looks back on the creator of Scrabble late in life, a long-overdue dictionary update rolls out. The “OK” controversy is okay and all, but I’ve been waiting my whole life to be able to play “EW.”

Crossword Proposals

Undoubtedly the most unexpected moment at a crossword tournament occurred this year not at the ACPT, not at Boswords or Lollapuzzola, but at the Pleasantville Crossword Puzzle Tournament, hosted by Shortz. One of the tournament puzzles turned out to be a springboard for Brendan McGrady’s very public proposal to his girlfriend, Amanda Yesnowitz — Yesnowitz, I’m not making that name up. She said Yes(nowitz).

Congratulations are also in order for Anna Sanders and Tessa Klein, who did things a bit more quietly. We’ve seen a few other crossword proposal stories over the years, but this may be a first for a non-heterosexual couple.

Crossword Science

Every year, it seems the question gets batted back and forth: do crosswords help one retain brain function or not? This University of Exeter study… probably will not settle the question, but it is admirably extensive, with over 22,000 participants confirmed so far and a projected 50,000.

Fusion Cuisine

Behold the crossword-sudoku union known as a “cluedoku.” (“Making of” interview is here.) And the cartoon-crossword fusion that was all but inevitable from The New Yorker, now that it’s known for both.

The New Yorker Non-Subscriber’s Dilemma

If you want to limit your magazine subscriptions but love reading about crosswords, the New York-titled venues ain’t gonna make life easy for you. For example, you could be reading about crossword art and politics or laughing at faces to make when solving the NYT, but only at the expense of some of your five free articles a month you could use to solve instead. (At least the YouTube videos have no strings attached!)

Just for Fun

How many 15x15 crossword grid-patterns can be made? The informal study listed here (scroll down to the header “Solution to the previous Riddler Classic”) has a couple of flaws (crossword grids are occasionally non-symmetrical, and no one would ever approve a grid with a solid border of black squares) but it still suggests strongly that the answer is north of 50 trillion.

Satirical not-newspaper The Onion takes us into a dark mirror universe — what if Superman were evil? What if certain corrupt politicians were mild-mannered philanthropists? What if Will Shortz were a serial killer?

Two of ESPN’s key content creators get into a solving contest.

Should you solve this bottle before drinking the whiskey, or after?

Bottom of the Barrel

Finally, the year’s most embarrassing project has got to be Wealth Words, described in a press release that somehow sounds both desperate and self-satisfied as “the next big thing in online crossword.” Let’s just say that I question its claim to be giving out even modest cash prizes when its idea of an award-worthy puzzle is a mostly-filled-in “grid” like this:

Uncrossed words make for cross solvers. Best wishes for a cross 2020!

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T Campbell

Writer of comics, crosswords and all manner of things.