Last month, I had a perfectly lovely time solving Jesse Cohn’s August 29, 2025 crossword in the New York Times. But after reading the constructor notes, I realized that there was an alternate version of the puzzle to consider – a simple change with the potential for important benefits as well as drawbacks.
Puzzle Spoilers:
New York Times: August 29, 2025 by Jesse Cohn
The Subject Matter
Friday’s NYT puzzle is traditionally a “themeless” crossword. But when I read the constructor’s notes, I learned that the puzzle was less themeless than I originally thought. From Jesse Cohn’s constructor notes in the daily Wordplay column:
“Four- and 15-Down are meant to be loose nods to two schools of thought (though imperfect, for sure, please afford me some cruciverbal license!). With those two in place, it took some wrestling to get the rest of the fill to play nice, but I’m happy with how it turned out and I hope it’s a fun solve.”
The two related answers (CREATION OF ADAM and CELESTIAL EVENT) give the puzzle sort of a “mini-theme,” which is a neat connection.
But something I found particularly interesting was how these entries went down rather than across. After all, themed puzzles conventionally contain horizontal theme answers – for example, my midi puzzles for Puzzmo, which often contain just two themers as well. One reasonable explanation for this convention is that horizontal words are the natural way to read the English language, and thus better suited for being recognized by the solver.
As I mentioned, I didn’t clock the “mini-theme” in this puzzle while solving, and I wonder if I would have had a better chance if those entries had been horizontal. It would have been an easy change to make: One of the geometrical joys of crosswords is that you can “flip” a grid along its diagonal – the across words become down words, and vice versa (as shown with the two grids below).
So it would have been a trivial change to make the “Origins of the Universe” mini-theme horizontal. Which led me to wonder: Was there another factor at play to affect to deter this choice?
Grid Aesthetics & Strong Starts
How do you start solving a puzzle? More specifically, do you tend to solve a) from the top to the bottom or b) from the bottom to the top?
Regardless of you individually being a complete freak, I’d wager that a large majority of puzzle solvers start with 1-across and generally try to solve clues from the top to the bottom. And if native English readers do indeed have an affinity for reading/writing horizontal words as opposed to vertical words, then flipping grids – and changing which entries are horizontal than vertical – starts to feel like a much more impactful choice.
With that in mind, does one of these grids initially strike you as more “exciting” to begin solving?
As you might have noticed, this is the same grid we’ve been talking about along with its “flipped version.”
To me, Version #1 (the original) is more appealing for my left-to-right, top-to-bottom inclinations. It feels more open to my eyes, and features some intriguing longer horizontal entries in 14-, 17-, and 18-across: entries with lots of possible answers and even a chance that I’ve never seen those words in a crossword before today.
Meanwhile, in Version #2 (flipped) I’m immediately faced with a lot of black squares in the top rows, separating a flurry of 3- and 4-letter words. Black squares mean less squares to solve, and short words means I’m far less likely to be surprised by a novel entry.
Version #1 might still make the mini-theme (of CREATION OF ADAM and CELESTIAL EVENT) harder to appreciate. But I think it offers solvers an initial impression more in line with the “spirit” of the themeless puzzle, i.e. prioritizing longer words and open space. So compared to Version #2, it’s probably more appropriate for a traditionally “themeless” day.
Yes, it’s important to acknowledge that these versions are fundamentally the same puzzle. But if solvers are inclined to start their solving with the horizontal entries near the top, that’s probably an area of the grid worth prioritizing – especially when it’s as easy as flipping a grid.
A Potential Rule of Thumb
All of this got me thinking: Can we come up with an actionable guideline for grid flipping?
And so, I hypothesized a flipping rule of thumb: In general, take the option that minimizes black squares in the first 4 rows.
The reasoning is as follows: If themeless puzzles want to prioritize that initial solver experience towards the top of the grid, then black squares can hinder that goal because they often create divisions and make words shorter. So fewer black squares can indicate longer words. As to why I’m choosing 4 rows specifically (as opposed to 3, or 5), it’s definitely a bit arbitrary. One argument could be that the 4th row is the first place where a black square can fit a vertical 3-letter word above it, and so a lack of black squares in that row means the top section is better connected to the rest of the grid. (Again: somewhat arbitrary.)
Anyways, it’s just a hypothesis. The real question: How does this proposed guideline stack up against actual puzzles?
I looked back at Friday and Saturday New York Times puzzles since July 1, 2025 to see whether the choices being made align with this rule. Out of 23 puzzles, 13* of them followed my “rule-of-thumb”; 7 puzzles, when flipped, had the same number of black squares in the first 4 rows as the original grid (meaning the grids were equivalent by my criteria); and only 2 published grids had more early-row black squares than their flipped counterparts.
NYT Themelesses, July 1 through September 20, 2025:
Rule followers: 54%
Neutral parties: 29%
Rule subverters: 8%
And no, I don’t think my slapdash guideline is always The Right Way, or that the “rule subverters” are missteps or “worse” grids. But I do think that this trend has actionable implications. The statistics, at the very least, help illustrate the design inclinations of other constructors and editors.
And if puzzle-makers are constructing crosswords that they themselves would want to solve (as I think we should all strive for), then I think the pattern offers insight into the solver population as well.
Final Thoughts
Crossword construction is far from an exact science. I don’t think there are often “right” and “wrong” answers, especially when it comes to something as murky and subjective and (relatively) trivial as “grid orientation.” And clearly, even my very-inspired-and-super-smart-”rule of thumb” has its own counter-examples and scenarios that require personal judgement calls.
Ultimately, we’ll never create a scientifically perfect puzzle, whatever that means. But I think we can at least come closer to crossword enlightenment, i.e. an understanding and appreciation of a puzzle’s aspects so we can make informed, conscious choices. And if this “top-row excitement” is something that other constructors and editors are thinking about (either explicitly or implicitly), then maybe it’s worth it for us to consider as well.
So flip that grid, and give it a fair shot! The results could be exciting: for you and your solvers.