Chess, the Daily Crossword, Abstraction, and the Progress of Society

Oreo, ahi, Ani, ore, aloe, Erie, area, idol, arena, odd, der, una, ural, oboe, B-team.

There, I’ve solved a third of tomorrow’s crossword puzzle for you. Or the next day’s. Pick a day.


* * *


There’s a visceral excitement in the potential offered by a blank crossword puzzle. As a self-contained unit, it’s seemingly as abstract as Sudoku or Latin Squares, a pure sequence of logic to be unraveled. But unlike so many puzzles, this one has relevancy, contains concrete associations that unfold as you progress. The objects, themes, and concepts that populate it arise from what you understand about facts, words, and ideas — in short, the real world.

A crossword puzzle calls upon knowledge in areas ranging from everyday items to titles of books and movies and plays you have to dredge out of your memory. It may include fanciful twists of wordplay that make you think hard to get to that aha when you solve it in the end. It combines logic, knowledge, and cleverness. And as you work your way through morning coffee and crossword, if all goes as hoped, you feel a little bit elevated: your mind clearer, sharper; you worked through — successfully — a cadre of recall and association and clever disguises communicated to you in hints by the editor. You feel you’ve taken yourself away from the prosaic for just a little while and engaged in something perhaps sublime in a small way, a pursuit that amplifies your intellect and reflects the culture that surrounds you, and which, most mornings, you are about to enter. All this is latent in the waiting puzzle.

And yet, often, there is none of this in reality. Often only mere echoes appear of what should be present. Have you noticed it? I can’t be the only one. More often than not, I make the effort more in hopes of the idea of enjoyment than actual enjoyment itself. There’s something missing. Each day’s puzzle feels rote yet abstract, spawning out of predictable word-banks and forming whimsical combinations of editorial expression which only nominally represent some cohesive theme. The majority of solutions are stock and store, commonly repeated one day to the next and almost certainly a significant portion used within any given week. Most remaining answers feel nonsensical, leveraged with heavy contortion to tie into their clues. Intentional variances in spelling and foreshortened clues leave only a semblance of relationship to a real-world vocabulary.

It seems unfair to complain — after all, there are only so many words that fit the specific patterns of tiles forming the standard 15×15 crossword puzzle. And so we see many of the same terms used over and over again, which is perhaps not surprising.  It’s hard to place blame when the cadence of the creation of these crosswords is daily and the subject matter is distinctly nontrivial.  There’s a natural upper limit to the words being used.


Early NYT Crossword Solution

New York Times crossword solution from 1963, via NYT public archives.


It’s worth noting that the current standard is not the only standard. Crosswords were published professionally in more variety in the past, in different forms and alternate layouts and sometimes even trading off a more sparsely populated puzzle for the ability to include different kinds of answers.

If you look back a few decades at the crosswords of the ’70s and earlier, you’ll see them. You can still find them now, actually; puzzles of all kinds are popular enough that if you scour puzzle and crossword sites, you’ll encounter crosswords large and small, modern and traditional, and with many new forms that never before existed. Look no further than Sporcle for some of the most quixotic of these. But they’ve largely disappeared off the primary drivers of the crossword: the daily newspapers, which, despite slowly disappearing over the precipice of traditional news media, maintain an impressive niche in some areas. Certainly if you search “crossword puzzle” most of the primary results will be from major news outlets. And they will almost all take “standard” modern form.

Is there a reason for this? I am no cruciverbapro; I do the crossword as a brief diversion and often find myself stymied on the Saturday puzzle (which tends to be most obfuscated). But it seems fairly plain to me that there is an expectation of densely-packed, relatively standardized crosswords, and that anything else is seen as amateurish, which is really a shame. There’s a lot to be offered by varying form and pattern, not the least of which is keeping the crossword in the realm of vocabulary rather than abstract patterning. A deviant crossword need not be a simple crossword (and a simple crossword need not be a bad thing as well, though perhaps for a different audience).

Maybe someone with better knowledge of crossword history can tell me if my assessment is accurate or if there are different driving causes behind this seeming standardization.

Regardless, the uniformity presented by this paradigm ensures that, being more densely packed, there is less wiggle room. Fewer ranges of words are available. I would claim, and with some fervor, that densely packed grids of predictable words prove no great enticement.

There’s an additional factor, too, that makes even the longer, better clues less rewarding: the lack of cultural cohesion.

In part, this is an unavoidable outcome of the (generally positive) shift in media consumption away from a few central producers, but the resulting fragmentation of culture means that what is commonplace and obvious to some proves incomprehensible to others, and vice versa. As recently as the ’90s, this was almost inconceivable. Think of Seinfeld: Most people in a certain population segment watched Seinfeld. Many of those people fell into the same grouping as those who would do the daily crossword.  Perhaps only the most highbrow of cruciverbalists would have skipped Seinfeld to the degree that a clue even referencing the show would be meaningless. In the ’90s, if you didn’t watch Seinfeld, you knew someone who did, and you probably knew the names of main characters and similar reference points.

Contrast Yellowstone, a reasonably popular show referenced fairly commonly in today’s crosswords (mostly for the names of one or two key actors). Yellowstone has had great viewership, and it’s likely to get better: several millions per episode, even over ten millions for some, and it’s possible it will grow as it is now reaching new platforms [1][2]. It’s not unreasonable to expect that many people are at least somewhat familiar with the show. But now look at Seinfeld: even early on, Seinfeld easily hit the teens and even twenty millions per episode, and later seasons regularly reached well into the thirty millions [3]. That’s a whole different scope of viewership. Combined with the more visual prominence of any major show at that time — you’d see it branded on anything and everything, and books, magazines, and newspapers all discussed them — it would be difficult to remain in complete ignorance of the show. This proves true for so many of the cultural artifacts in decades past, theater, books, movies, even news. There have always been different demographics and differing interests, but there were a lot more areas of common culture to point to where it was something that everyone knew.

Things that everyone knows are a lot harder to find now. Even a massively popular show on Netflix, Hulu, etc, is less familiar outside its key demographic. Then there’s more niche content: self-hosted podcasts, cultic YouTubers, infamous TikTok stars, high-brow anime, niche comic books. Each audience individually is relatively small and self-contained (with some exceptions, as they leak outside their spheres and into public consciousness), but each carves off its own unique slice of the cultural pie in viewership that often has increasingly little overlap with the next person’s. We all fall into this trap sometimes. The more we tell our friends about the shows and interests we know, that we like, the more we construct and dive into our own little bubbles of culture, the less anybody else’s makes any sense to us at all. It’s not just an unknown, its an incomprehensible, alien world.

So again, maybe it’s wrong to exactly blame the editors of crosswords for likewise occupying such bubbles — we all live in one, no matter how hard we try to avoid it. There’s just too much content to be familiar with even all of the more popular sub-genres. Yet again I also can’t help but feel that I’m not the only one left staring dumbfounded at a crossword clue that’s written like it’s complete common sense but means absolutely nothing to me, and then when I do finally manage to solve it — usually through pattern-matching rather than getting the reference — I have to go look up the answer itself, just to learn that it’s some minor actor, some cryptic reference to a show, or some localized slang that I’ve somehow managed to completely avoid discovering until now.

I’d like to think I don’t totally live under a rock. I try to maintain a fairly broad variety of friends and stretch my conversations to at least comprehension of the commonly-viewed trends out there. But the experience of the daily crossword tends to set me straight in that regard — either the editors live in a completely isolated bubble of culture, or I do.

Probably both.

One more complaint: Many of the words in a modern daily crossword are not English. French, German, and Spanish rarely miss a day. They are tantalizing bait for the editor — the most commonly used words taken from these wells are short and vowelful, the ideal supplement to the increasingly congealed form of the daily crossword.

All these failings and limitations were taken to a pinnacle in one crossword that seemed to make very little sense to me even after working out about half the clues, and this was, I discovered, because many of the words were not words, but words with a seemingly random letter appended to the end of each of them, which, when flipped to form the crosswise answer, was a phrase related to the nominal theme of the puzzle.

Here, finally, was a crossword so tortured, clues so divergent from their answers, that a good portion of the puzzles entries ceased to be actual comprehensible words. There are more common examples of this in words being truncated or flipped, but to my mind this falls into a different, if equally frustrating, category since those at least follow a pattern, such as swapping all ‘s’s for ‘c’s and so on.

Here, on the other hand, the clues of the crossword were not even themselves hints of how to manipulate a given word to end up with some other combination of word. It was merely words that were sacrificed on the altar of the greater answer.

I’m not going to name or reference the origin of this puzzle as that would be inappropriate, and it wouldn’t be too hard to figure out if someone really cared to, but this culminating experience has really taken my enjoyment down a peg on crosswords. I still dabble some days, but my heart’s not in it.

As a side note, it’s sometimes entertaining to make your own crossword — there are some good tools out there, and if you’re willing to put a little time and brainpower into it, there’s some reward in crafting a puzzle that’s built just for you. But it’s not a brief process, at least not if you want a unique result, and even with those modern tools, how much time are you going to put into creating something when it’s not your job, not even a principal hobby, barely a minor hobby, more a daily indulgence.


* * *


This made me think about what this change of the crossword really meant, and I started to think about the different types of crossword, and the sometimes subtle dividing lines that separate what my definition of a “good crossword” is from the esoteric, abstracted puzzle within a puzzle that so repelled me.

In fact, the conversations that I’ve seen online about crosswords, by those who are truly enthusiasts, seem to revel in the level of abstraction and the desire to perform this word mapping, whereas I suspect — but can’t prove — that most of the everyday people who would have previously done a crossword no longer do. I know of a few examples outside myself where this is true, but that’s hardly a basis by which to judge.

Instead it pays to approach this question from another angle. A useful analogy here might be chess.

I don’t know how many people remember this phenomenon, and in fact it was mostly gone by the time when I was first looking at newspapers for anything but the comics, but it used to be very common for most major newspapers and a lot of minor ones to include chess problems, boards set up in a certain way you could attempt to solve, much as you would with a crossword, or demonstrations of various matches that you could follow.


Chess puzzle in the New York Times in 1963


But these are gone away — and why?

Have people lost interest in chess? You could easily assume so: Certainly, the Luddites among us, in whose ranks I sometimes fall, would say that people have lost interest in the “traditional entertainments” like puzzles and more thoughtful games; people are interested in other things, absorbed by media — and that’s true, and yet, to cite just one example, is incredibly popular, receiving hundreds of millions of visits a month and ranking within the top several hundred sites overall (even higher in the US) [4][5]. Chess remains well-liked among many segments of the market (many of which overlap with the newspaper-consuming market). A recent chess championship famously took the limelight, for slightly more unpleasant reasons than pure enjoyment of the game, but the point remains that the “average person” is not the stranger to chess that more closeted minds would assume. A lot of people play chess, even if just sometimes. I have even met rehabilitated prisoners who used their time in prison to refine their tactics in the game.

So why isn’t chess in most papers? You won’t find chess puzzles even in most online versions of various daily papers.

My conclusion, with which I hope you will either agree or present me with a counterargument for, is that it became esoteric.

The people who remain interested in chess don’t think of it as an everyday activity, they think of it as a rarefied activity meant to stretch their brains and occupy their time with something a bit loftier (even if they would never use these words to describe it).

Of all the players I’ve ever met at this point, and I’ve met a fair number, they tend to fall into one of two groups: The first group, the dabblers, play on occasion. Like myself, they enjoy chess as a concept, appreciate the chance to think and examine the board and plot out strategies and test them against a friend or nemesis. And they’ll enjoy playing, until they run across someone from the second category, the avid hobbyists who really like chess, and the first guy will get completely steamrolled.

Because you get really good at chess for the same reasons that a computer is good at chess. One, you’ve played enough to memorize the standard openings and endings, the correct ways to begin and end a game and respond to your partner by selecting the appropriate sequence, maybe slightly modifying it if needed, which is not often. And then, two, by process of playing hundreds or thousands or tens of thousands of games, perhaps supplemented by reading chess theory, you understand the construct of the board such that you can intuitively tell what is likely to be the next optimal move in this scenario.

Success here comes somewhat from strategic thinking, but much more so from an intense familiarity with the peculiars of the internal mechanisms of the game, the panoramic comprehension of likely moves to the extent that you know what the opposing player is likely to do next and therefore which move you should make. This is a barrier I cannot cross, a barrier a lot of people cannot cross, or don’t want to, either through lack of time, lack of interest, or lack of raw brain power in some cases, honestly — that’s partly my limitation.

I suppose most of us could get past that hump if we were willing to spend the time memorizing patterns and strategies, but it would be time consuming, and a challenge, and the frustration along the way just proves not worth the while. And so the lingering popularity of chess is less and less with those in the first category, and much more in the second category.

And that is why, I’m almost sure of it, chess is no longer in the paper. It’s no longer for the layman who wishes to improve himself a little bit that day. It’s not for the average Joe who considers himself a bit more white-collar than he is blue-collar, for the person who is maybe a tradesman but keenly intelligent. It’s for someone — in any rung of society, doctor, lawyer, tradesman, or convict — who is really into the esoteric value of chess, the abstract permutations of what today’s game might prove to be.

Casual, largely amateurish play (from the ranking’s point of view, anyway) is just not part of the chess experience anymore. Chess, by and large, has gone past those bounds and I wonder if crosswords will, too, for the same reason.


* * *


Putting chess aside again, the particular crossword that I mentioned earlier, and those of its ilk, that have been building within me this head of steam that came to a front now took me to want to represent in more concrete terms my dismay and disdain. And so I took to ChatGPT — not having the wherewithal or the desire to attempt to it myself — to write out a little story expressing the contrasts and frustrations in this bifurcation of the puzzling world, and after just a couple iterations, it came up with something, and I think it’s pretty good. And here it is.


In the chrome-touched twilight of 2073, Gerald J. Fitzsimmons III, of the esteemed crossword-conjuring Fitzsimmons lineage, sat in his penthouse office overlooking the cityscape of New York. His eyes were fixed on the 15×15 grid spread out on his sleek, holographic desk.

He traced the glow of the clue for 7-Across. A grin touched his lips. The clue: ‘Neoplasmic metaphor in the ironic narrative of Zorgon-5’s sixth quadrant (3rd revolution)’. An artful nod to the quantum fiction genre, a casual yet profound exploration of cosmic uncertainty. He could already visualize the threads of discussion this would spur in the crossword forums, the potential for scholarly exploration.

There was a fervent joy in it. For Gerald, it was the delicious thrill of unraveling the cosmos and stitching it into a tiny grid, a symphony of knowledge and culture. It mattered little to him who could, or would, attempt the solution. He was painting with a palette of words and wisdom, and each clue was a stroke on this canvas of his design.

“Now that’s a crossword!” he murmured to himself, basking in the intellectual reverberation of his creation.

Meanwhile, several miles away, under the fluorescent lighting of his Toledo auto shop, Randy struggled with the same crossword. The clue, that damned clue: ‘Neoplasmic metaphor in the ironic narrative of Zorgon-5’s sixth quadrant (3rd revolution)’. It echoed in his mind as he cleaned his grease-blackened hands.

He glared at the nonsensical jumble of words, the labyrinthine puzzle as inaccessible as the wealth of the customers whose luxury electric vehicles he serviced. He missed the old crosswords, their worldly clues hinting at familiar corners of life, the satisfaction of ink filling squares, the joy of catching a clever play on words.

Randy tossed the newspaper onto his workbench, the page crumpling under the weight of the spanners. “Jes’ more of that high-minded nonsense,” he grumbled, his hands returning to the stubborn nuts and bolts of the physical world in front of him. His grip on the wrench felt real, solid, unlike the abstract gibberish the world seemed to be obsessing over.

And so, as the city spun on in its chaotic dance, two men, worlds apart, shared a moment of connection over a grid of black and white squares. One, lost in the delight of complex creation, and the other, recoiling from its esoteric excesses. In this peculiar dance, the humble crossword had taken on a life of its own, its 15×15 universe birthing a new paradox, simultaneously celebrated and detested. And in that, it perhaps became the most accurate mirror of its time.








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