The Best Crossword

They might well be right; three years ago, they indisputably were right. But recently, a rival has emerged upon the crossword veldt to challenge the Times‘s supremacy and its puzzle editor, Will Shortz. This novel creature is the New York Sun crossword, and is driven by the vigor of its puzzle editor, Peter Gordon, who used to work for Shortz at the Times. For the first time in recent memory, the answer to the question posed in the opening sentence of this article is seriously debatable.

As a normal American, I have an unhealthy fascination with the concept of “best,” so I decided to run an experiment to see which of these two puzzles would come out on top in head-to-head competition–a crossword smackdown, if you will. But before we get to that, a little history to set the scene.

The New York Times crossword established its household-name brand dominance under the skillful eye of Margaret Farrar, who edited the crossword from its debut in 1942 to her retirement in 1969. She was followed by Will Weng, who edited to mostly favorable reviews until 1977.

At that time, the puzzle was regarded as the best daily crossword in the land, and it was. But under the editorship of Weng’s successor, Eugene T. Maleska, the puzzle’s reputation began to slide, at least in crossword circles. Maleska was known for filling his puzzles with “crosswordese,” those painfully obscure words you never see anywhere in life outside of the crossword page. This made many of his puzzles less a fun, fair challenge than an unsolvable, headache-inducing battle with a set of encyclopedias. The average well-educated person simply couldn’t be expected to know that LOA, in an infamous clue example of the era, was a “Town in Utah”–a town with around 250 people, as it turned out.

The so-called “New Wave” style of crossword puzzles, which shunned obscurities in favor of familiar words, humor, and pop culture, held little appeal for Maleska, and when he passed away in 1993, the Times puzzle was in need of a savior to keep pace with the zeitgeist. Rival editors like Stan Newman at Newsday had begun successfully syndicating their own

daily crosswords, pointing out in their promotional literature how obscure and practically unsolvable some Times puzzles had become.

Enter Will Shortz, the genial former editor of GAMES magazine, who famously possesses the world’s only college degree in enigmatology (the study of puzzles). Within weeks of his hire in 1993, the reputation and the reality of the Times crossword were back in alignment: Artistic standards were raised, puzzle writers’ fees were increased, and the Times‘s puzzle audience widened.

Competing daily crosswords began to have more trouble syndicating their puzzles, and started to position themselves not so much as rivals to the Times, but rather as “somewhat easier than the Times crosswords” or otherwise different in some way. There were other good daily puzzles around, but the big kid on the block had reasserted himself; artistically, the Times was back on top. It had no rivals.

Until recently. When the New York Sun began publishing in 2002, Peter Gordon jumped ship from the Times to edit its crossword. His intention was to make the Sun puzzle the best in the country, no easy task. But Gordon, with remarkable energy, has applied innovation after innovation to the crossword editor’s job, and the results have gotten puzzle people talking. For example, he virtually never allows himself to repeat a clue, even in crosswords published years apart, which leads to even frequent puzzle words like ALI and ERA being clued freshly every time.

After solving a few dozen puzzles from the Sun during the past year, I was impressed, and discovered that others were, too. On the New York Times crosswords forum, moderator Will Johnston ranked the Sun puzzles as being “tougher” than the Times puzzles (not necessarily an indication of quality, but still interesting). Rating the Sun as tougher than the Times “may be controversial,” Johnston wrote, “but I think Peter Gordon’s clues are in general harder on the tricky days.”

Another forum member conducted an informal survey on which of the two puzzles readers preferred, and solvers came down about 60-40 in favor of the Times. Not bad for the challenger, especially since Gordon disputed certain aspects of how the survey was conducted.

In other words, it’s time for a crossword smackdown, so let’s do it! I want to know what the best daily crossword puzzle in the country is, and so do you. By general consensus, this title bout is between the venerable New York Times, under its brutally witty editor Will Shortz, and the upstart New York Sun, under its scrappy, full-of-new-ideas editor Peter Gordon.

Methodology: For the low, low price of one dinner, my long-suffering girlfriend printed out 30 Times and 30 Sun puzzles from the papers’ websites, cut off the bylines and titles, and blacked out the copyright beneath the puzzles. This took away all identifying features and left me solving without knowing which puzzles were which. All 60 puzzles were published in April or May of this year.

(Disclosure: I’ve written a few dozen crosswords for Shortz in the Times, and have worked with Peter Gordon on several crossword books. I respect both greatly and have no grudge, bias, or bile against either, but I solved blind anyway to remove any possible slant, conscious or not.)

I solved all 60 puzzles, then assigned each one a score for artistry and a score for technical merit, each on a scale from 1 to 10. I also gave myself the option of assigning a star, worth one bonus point, to any puzzle that had some extra flash of brilliance.

Of the 60, three puzzles (two Sun and one Times) had to be discarded from the tally for various reasons. One Sun and one Times puzzle I already happened to have solved, and another Sun puzzle was a crossword variant that wouldn’t fit in with my analysis. Out those three went, and then, to even things up, I discarded one average-scoring Times puzzle from the tally, leaving 28 crosswords from each paper to be compared.

Because the Sun publishes only Monday through Friday, I omitted all Times Friday and Sunday puzzles from the competition. This left the two papers going head-to-head on Monday-through-Thursday puzzles, then the Friday Sun and the Saturday Times going at it. This seemed fairer to the Times than omitting its Saturday puzzle, since the Saturday Times is generally the toughest of the week.

Before we get to the results, let me stress, paradoxically, both the subjective and objective natures of judging any kind of art, crosswords included. Some people prefer Beethoven to Mozart; others prefer Mozart to Beethoven. There is no “better” choice between the two. If, however, someone prefers Ashlee Simpson to both, we may discount their musical opinion without guilt. What we have here, you might say, are the Mozart and Beethoven of crossword editors; if one prefers Ashlee, the TV Guide crossword will provide it. For better or worse, then, this is an article for crossword snobs.

Enough qualifying remarks: This is America, dammit, and people want a winner. And that winner is, by a score of 432 to 419: The New York Sun crossword.

The Sun outscored the Times by the smallest possible margin in artistry (210 points to 209), and by a rather larger margin in technical merit (214 points to 206). This isn’t a huge spread, but broadly speaking, the technical score was higher for the Sun because of its somewhat better job of keeping crosswordese out of the puzzles. For instance, I was surprised to see both YSER (a small river in Belgium and France) and ESNE (a medieval serf) in one Times puzzle–both words are oft-mocked instances of crosswordese. This example was atypical of the Times puzzles, but the Sun‘s grids were a bit cleaner overall.

The Sun puzzles also had slightly punchier clues, probably thanks to Gordon’s no-repeat rule. Shortz’s dry wit comes through consistently in the Times, however, on clues like “Leaves for a drink” for the answer TEA.

Twelve of the 56 puzzles earned a star (and a bonus point) for being especially brilliant in theme, construction, cluing, or all three. Of these 12, 8 were from the Sun and 4 from the Times. The Times did score the top overall single puzzle, however, the only one of the 56 to receive a 10 rating in either category–and it got a 10 in both artistry and technical merit (and, unsurprisingly, a bonus point).

It’s a stunning 56-word themeless puzzle from the Saturday, May 7 Times, written by the much-admired North Carolina wordsmith Patrick Berry. It stands out for its total lack of crosswordese and abundance of lively words and phrases in the grid–both extraordinarily difficult to pull off in a grid as wide open as this one. It’s one of the most impressive crossword puzzles I’ve ever seen.

Despite the Sun‘s slim win, there’s no real threat to the Times‘s cultural and syndication superiority. The Times (circulation 1.1 million) syndicates its puzzle to hundreds of newspapers around the country, meaning its crossword is probably solved by a few million people on a given day. The Sun (circulation 50,000) does not syndicate its puzzle to any papers, meaning its crossword is probably solved by only a few thousand people on a given day. Thanks to the Internet, however, you can solve it online at www.nysun.com. (Sun puzzles are free of charge. Times puzzles, available at www.nytimes.com if you can’t find them in your local paper, cost $34.95 per year.) Because it only appears Monday through Friday, the Sun puzzle cannot be easily syndicated to papers that publish six or seven times per week.

Capitalism’s finest spiritual feature is that it elicits ever-improving work from us. If and when it feels the need, I have no doubt that the Times will throw its institutional weight behind punching its puzzles up to even higher heights. Then, if we are lucky, the Sun will feel the need to reply in kind.

I look forward to the ride, and suggest readers enjoy both crosswords, with Wolfgang or Ludwig playing in the background, as you prefer. But please, not Ashlee. Not with these puzzles.

Matt Gaffney is a professional crossword writer living in Washington, D.C. His book, The Complete Idiot’s Guide to Solving Crossword Puzzles and Other Word Games, will be published in October.