For the past four days, I’ve been using my “Crossword Trainer” to memorize previous crossword clues and answers. As of today, I’ve memorized 3,200 out of the 12,707 clue-answer pairs.

This has been a lot of work (eight hours, so far), so I should probably try to quantify what I’m gaining by completing this portion of my training. After all, if I do choose to complete this training, it would require an investment of another 24 hours, which is substantial.

When I first conceptualized the “Crossword Trainer”, here’s how I hoped things would go:

I memorize a lot of clues and answers Many of these clues and answers are reused in new puzzles So, for a given new puzzle, I can easily fill in a large portion of the grid just using memorized answers With the memorized answers in place, I should have enough puzzle momentum to complete the rest of the grid without too much difficulty

In other words, I hope that I can solely use memorized answers to surpass the solve threshold of any given puzzle (where the solve threshold is the percentage of completed grid where, if reached, I would be able to fully complete the rest of the puzzle).

I haven’t yet quantified my personal “solve threshold” (which would also need to take into account puzzle-by-puzzle variance), but, for now, I can probably eyeball it well enough.

Therefore, let’s look at yesterday’s puzzle and see how much of the grid is represented in my “Crossword Trainer” dataset (i.e. how much of the grid is filled with answers that I have memorized or that I will eventually memorize?).

Thus, with perfect recall of every answer from my training set, 45% of the grid (as highlighted above) would theoretically be “automatic”.

Then, if I layer these “automatic” answers on top of the answers that I was able to deduce yesterday on my own, the grid would look like this:

This grid is certainly past the solve threshold, and would be fully solvable.

In other words, it seems that if I finish memorizing all 12,707 clue-answer pairs, I should be able to successfully solve a Saturday NYT crossword puzzle with reasonable ease.

Right?

Not quite. Unfortunately, the analysis I use above is flawed in one very major way: Just because a memorized answer is in the puzzle doesn’t mean that the memorized clue relates to the new clue in any recognizable way.

In other words, the same answer with very different clues is far from being an “automatic” fill-in.

For example, take the answer to 62-Across, TRE.

From my dataset, I’ve memorized the corresponding clue “30% of dieci”. But, what if, instead, TRE was clued like this: “Amount over due?”.

These are both reasonable clues (dieci is Italian for ten, due is Italian for two, and tre is Italian for three), and yet, there’s no way that my knowledge of one translates to the other in an “automatic” kind of way.

If my brain wasn’t primed for Italian, I’m not sure I would catch the “due” misdirection.

And, of course, this is a benign example. These clues happen to be fairly related. Some answers can be clued in extremely different ways.

So, I should redo my analysis of yesterday’s puzzle, where I only highlight the answers that both 1. appear in my dataset and 2. have clues in my dataset that are directionally related to the clues from the actual puzzle.

If I do that, here’s what the grid looks like…

Only four answers would have been automatic or nearly automatic. Every other answer was clued in a completely different, unrecognizable manner.

This is much less promising, and clearly very far from the elusive puzzle threshold.

Thus, it begs the question… Should I even continue training with the “Crossword Trainer”?

Despite this less-than-optimal analysis, I still think that I should continue — at least for another week.

Even if I’m not getting automatic fill-ins, I do seem to be gaining other useful, but not-yet-quantified skills: 1. I’m learning to better recognize common types of misdirection; 2. I’m building some sort of statistical mental model of which letters are most likely to sit next to which other letters (sometimes as a function of the clue, if it’s a foreign word, etc.); 3. I’m learning what the most commonly used answers are, which I still might be able to recognize in the grid, even if the clue doesn’t match the clue I’ve learned; etc.

For the next few days, I’ll proceed with this training method, but I’ll need to figure out a better way to quantify my progress moving forward.