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Indie Crossword Puzzlers Are Shaking Up A Very Square World

Gawker wasn’t the only irreverent, iconoclastic internet media property to say farewell recently. To a much quieter dirge, the BuzzFeed crossword puzzle published its final edition this month. Its editor, 23-year-old puzzle wunderkind Caleb Madison, for whom this was his first job, left the company to strike out on his own.

The BuzzFeed crossword, which launched in October, promised a millennial upheaval to the musty crossword genre: an internet-native, slang-fluent, pop-culture-obsessed puzzle aimed at young solvers. There was hope, given BuzzFeed’s large amounts of traffic, that it would serve as a meaningful competitor to the starchy, hegemonic New York Times crossword. “BuzzFeed Is Revolutionizing the Crossword Puzzle,” an Observer headline declared last year.

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It didn’t. Yet while BuzzFeed’s puzzle revolution fizzled, a devoted band of ragtag agitators remains devoted to the cause. A vibrant ecosystem of independent crosswords — “indies” — exists on the internet, its component puzzles multiplying and evolving, finding their niche and trying to find ways to survive. And some of them can outrate the gold standard over at the Times.

“I think of the indie world like we’re all craft beer brewers,” Brendan Emmett Quigley, a professional puzzle constructor, told me. The Times is a Budweiser lager; the indies are small-batch saisons and IPAs.

“My favorite thing about indie puzzles is the timeliness,” Neville Fogarty, an avid indie solver who helped found the Indie 500 crossword tournament, told me. Indie puzzles don’t have to wait months in a publication queue, as they would at the Times. They also aren’t subject to the stylistic constraints of a large media institution. Topics and themes, however recent, modern, niche or profane, are fair game. Nor are they subject to the physical constraints of a major newspaper. With few exceptions, all daily Times puzzles use 15-by-15 grids with rotational symmetry, a convention indies can and do break.

Over (craft) beers recently, Ben Tausig,1 the editor of the acclaimed indie American Values Club crossword, reflected on the early days of indies, over a decade ago. “We were all out in the woods,” he said. “Papers were dying, papers were dropping their crosswords.” And so some crossword designers decided to go it alone. A risky proposition, but one that came with aesthetic upside. These sylvan constructors could rewrite the stylebook. “Crosswords were staid, you know? As much as I enjoyed them, there was always this feeling that the voice of the Times was not my generational voice. It was like, what if you made a crossword about rap, or something? That felt really radical at the time.”

Criticism of the Times puzzle seems to have expanded of late, beyond the stylistic and into the political. It’s not just that the Times puzzle is staid, or geared toward olds. It’s been accused of tone deafness on issues of race and gender. A recent clue for the answer HAREM was “Decidedly nonfeminist women’s group,” and the clue “Exasperated comment from a feminist” led to the answer MEN. “Gangsta rap characters” were THUGS.

But Will Shortz, the Times puzzle editor since 1993, is an icon for a reason. All the constructors I spoke to praised him for elevating the Times puzzle to its current station. “The Times’ job is arguably much harder, because they have to walk that thin line of making sure everyone is included,” Quigley said. It’s come a long way, too. The Times published its first crossword in 1942. If you scrape off a thick layer of dust, you’ll find a puzzle riddled with obscurities (the poets CRABBE and TASSO, the seaport HAGI, the Dutch town EDE) and ditchwater-dull clues (both IAN and YVON are clued as “Man’s name”). And even if some indie puzzlers would like to foment a revolution, it already took one to get the Times to the solid position it’s in today. Shortz oversaw a transition away from the dryest trivia to a puzzle that does include some popular culture. He has said that anything the paper covers should be fair game for the crossword.

“The Times’ crossword audience is broad, from teens up to as old as people get,” Shortz told me in an email. “But the average [age] is higher than that for the indies. So in terms of overall tone and cultural references, the Times puzzle will skew a little older than the indies.” Shortz also mentioned the need for the Times puzzle to have a longer shelf life than the indies, which means it eschews some timelier subjects. The puzzle appears in syndication six weeks after its original publication, and sometimes in books years later.

PUZZLE AVG. USER RATING
Matt Gaffney 4.0
Newsday 3.9
The Washington Post 3.9
Crossword Nation 3.9
Fireball 3.9
Brendan Emmett Quigley 3.7
BuzzFeed 3.7
American Values Club 3.6
Los Angeles Times 3.6
The New York Times 3.5
Wall Street Journal 3.4
Chronicle of Higher Education 3.3
CrosSynergy 3.3
Jonesin’ Crosswords 3.3
Boston Globe 3.1
Most highly rated crosswords

Includes puzzles appearing at least ten times. Ratings are out of 5.

Source: Diary of a Crossword Fiend

The Times’ puzzle, though, isn’t the most highly rated on the Web. Indies may be ragtag, but their quality can be remarkably high. The popular blog Diary of a Crossword Fiend lets readers rate a selection of puzzles each day, from one to five stars. Indies do well, with indie icon Matt Gaffney’s topping the list and American Values Club and Quigley’s puzzles averaging above the Times so far this year. (Note, of course, that these ratings are subjective, and come from a highly selected sample of the universe of crossword solvers, namely those who rate crosswords on a crossword blog.)

But that the indies are well-received doesn’t make them well-compensated. They’re wrestling with the same confusion about sustainable business models as all the other media upstarts.

The New York Times has it relatively easy, with nearly 200,000 digital crossword subscribers, good for over $2 million in revenue in the first quarter of 2016, according to a company press release. When you figure in the hardcopy subscriptions and newsstand purchases due to the puzzle, plus the countless book collections, the Times crossword puzzle is almost certainly worth well north of $10 million a year. (The Times wouldn’t comment beyond what was disclosed in the press release.) Little of that money goes to the constructors: At its rate of $300 for a daily puzzle and $1,000 for a Sunday, I estimate that a little less than $150,000 a year is paid to the crossword constructors themselves.

Outside the Times, though, monetization approaches vary wildly. The American Values Club crossword, the indie edited by Tausig, is subscription based. A year’s worth of puzzles is $20, or you can get a single puzzle for a buck, and proceeds are divvied up among constructors quarterly. Depending on the quarter, this model can yield more than the Times’ $300-per-puzzle rate, according to Tausig. “I’ve been a constructor for a long time, and also because I’m a hardcore Marxist, I want to put my money where my mouth is,” he said. Constructors there also retain some future rights to their puzzles. Tausig didn’t give me a precise count of his subscribers, but said there were no fewer than 3,000.

Quigley, who runs an eponymous site, was inspired by Radiohead’s 2007 release of “In Rainbows” when he created his pay-what-you-want model. He publishes free puzzles on Mondays and Thursdays, and provides a “tip your constructor” PayPal link on his homepage. Between direct payments and the advertisement it provides for other paying puzzle gigs, Quigley estimated that his site is responsible for two-thirds of his income. He claimed an average of 12,000 people solve a typical puzzle on his site.

And Matt Gaffney — whom other indie constructors described to me as the “juggernaut” and the “silverback gorilla” of the field and who tops the ratings list — oversees a mini-factory that publishes eight puzzles a week. About a year ago, Gaffney switched to a subscription-only model for his daily puzzle ($24 a year) which, he told me, has 500 to 600 subscribers. “It seems to be kind of the wave of the future,” he said. “But I think big media, regular media and indie puzzles will always coexist and coevolve for the foreseeable future. I don’t see one putting the other out of business.” Despite that, indies “are where all the crazy, new, fun stuff is happening.”

In many ways, the crossword tumult mirrors that of the broader media world, pockmarked with hirings, firings, launches, closings and scandal. BuzzFeed hit the brakes, and USA Today ousted its crossword editor in May. But others hit the gas. The Wall Street Journal added a daily puzzle last September, and The Washington Post tapped a new crossword constructor in November. And Slate, stalwart of internet media, will feature the American Values Club crossword in its paid section, Slate Plus, starting in September.

Madison, the former BuzzFeed editor, who has interned for both Shortz and Tausig, is heading back to the indie world himself. According to Madison, the BuzzFeed puzzle’s average 40,000 to 50,000 views didn’t justify its cost at the virally oriented site. (I emailed BuzzFeed for comment but have not yet received one.) He recently announced a new crossword project called Solve the Internet. Details were sketchy, but the description he gave me was heavy on “internet” and “social.” Madison wouldn’t offer a specific launch date but said to expect it soon.

“I don’t understand what he’s talking about, but that’s a fantastic thing,” Quigley, 42, said of Madison’s puzzle ideas. “If we don’t go out and try to bring in that younger generation, we’ve got the buggy whip, and we’re gonna get blown out by something else.”

Footnotes

  1. It was Tausig whose tweet, about a suspiciously duplicated puzzle, eventually led to the FiveThirtyEight investigation into accusations of plagiarism against the crossword editor Timothy Parker.

Oliver Roeder is a senior writer for FiveThirtyEight.

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