Puzzled: The Story of the Crossword-Creating Caltech Alum

Steve Ginzburg relishes constructing crossword puzzles for many of the same reasons he appreciates computer science. Publication in The New York Times is a bonus. 

Cyber security analyst Steve Ginzburg (BS ’98) moonlights as a cruciverbalist.

Cyber security analyst Steve Ginzburg (BS ’98) moonlights as a cruciverbalist.

By Judy Hill

Steve Ginzburg (BS ’98) was only a few years post-Caltech when he caught the crossword bug. On a trip home to Santa Cruz to visit his parents, Ginzburg, who was working as a software engineer in Santa Barbara at the time, was intrigued by the puzzles his empty-nester parents tackled at breakfast. 

It was not the challenge of solving the clues that held his attention, though. “I thought about it for a few minutes,” he remembers, “and I realized, ‘You know what, these are probably more interesting to create than they are to solve.’” With that, he grabbed a piece of graph paper and started make his own puzzle. 

Humbled by the difficulty of the task, Ginzburg contacted “a very active, supportive community of crossword puzzle constructors” and found a couple of puzzle veterans who coached him by email. In 2006, he had his first puzzle published in USA Today. The following year, one of his puzzles was accepted by legendary puzzle editor Will Shortz and published in The New York Times, the gold standard for crosswords. 

Other newspapers, including the New York Sun and the Los Angeles Times, have published his puzzles over the years, and though the puzzle pursuit has taken a back seat to parenthood and his work to improve safety-critical automobile software, Ginzburg is as much a crossword puzzle fan as ever. He attributes much of that interest to his training in computer science. 

“Filling a grid with interlocking words is a very interesting problem from a computer science perspective,” he says. “It comes from a class of problems where there is no guarantee of a perfect solution. And so you have to use heuristics; you have to apply intelligence to it to try to find a solution that you know isn’t going to be optimal but is going to be pretty good.” This, he says, is where the artistry of crossword puzzle creation meets the science of computer science. 

For Ginzburg, the real pleasure in both solving and constructing a crossword puzzle lies in the theme, the clever idea or piece of word trickery that unites a puzzle’s longest answers. 

“It’s really the most critical part of the puzzle, certainly if you want to create a marketable puzzle,” says Ginzburg. “If it’s a daily puzzle, you need to come up with three or four or five themed answers that are all consistent and fit together and make sense. For a Sunday puzzle, which is larger, it’s more like six or seven.” 

Ginzburg remembers having particular fun working with a theme based on phrases that start with a pair of letters in consecutive alphabetical order that are an abbreviation. “So, I had ABPOSITIVE, which is a blood type. I had VWSCIROCCO, which is a car I once drove, and UVEXPOSURE. A commentator on a blog noted that he got as far as UVEXP but then figured with that odd letter lineup something had to be wrong in the crossword, until he worked out the theme.” 

Ginzburg keeps a file for theme ideas that he started to think about but never used. One such idea is based on a phrase that had suddenly come into the language: fake news. “I thought, ‘OK, I’ve got to do something with that.’ Will Shortz in particular has pioneered the idea of crossword puzzles being timely and interesting and topical.” Working with the idea of “kind of nonsensical” phrases, Ginzburg jotted down the following: 

Clue: Shocking discovery: tiny boats paddled by sprites! 


Clue: Oliver Twist’s so-called boss shows his delight— you won’t believe why! 


Clue: Sign of the times, if not The Times 


“I never managed to make this into a puzzle,” he notes ruefully. “I just never got the theme to work quite right. I couldn’t come up with enough words or phrases that were amusing enough or the right length.” 

Once the theme is set, the next challenge is to create the grid and fill it with words that are reasonably well known. “Many people don’t realize this,” says Ginzburg, “but the difficulty in the crossword puzzle comes not from the words being obscure but from the clues being clever. That’s the difference between a Monday puzzle and a Saturday puzzle [the most difficult of the week].” 

Prior to the Will Shortz era, he notes, crosswords were filled with arcane words and “all sorts of crazy things that nobody had ever heard of,” but now the entire industry has gone in the direction of making the puzzles more accessible, putting the burden on making the clues, the last part of the process, trickier to add a degree of difficulty. 

“There’s a whole art to clue writing,” says Ginzburg, and, particularly for common three-letter words, it can be challenging. Ginzburg is especially proud of one clue he came up with for the word AWL (“Spiked punch?”) that even surprised his editor. 

A printable full-page PDF of this crossword can be found  here .

A printable full-page PDF of this crossword can be found here.

Though most crossword constructors today use grid-filling software, Ginzburg insists it does not make  creating a crossword less challenging. “Grid-filling software will tell you, first of all, if your grid is fillable. It will also help you figure out possibilities, like, ‘Here are half a dozen different words that could fit in this slot.’” Still, he says, even with the software, there have been times when he has had 90 percent of the puzzle filled but then found himself backed into a corner. He says, “I have to use this really awful word up in the northeast corner in order to finish it. So, do I put that in there and hope the editor lets me get away with it, or do I come up with a clever clue, or do I unwind three quarters of the puzzle and start over and pursue a different direction?” 

This, Ginzburg says, is where heuristics play a role in filling the grid. “A computer program is not going to give you heuristics. There has to be human intelligence applied to it to try to come up with the best possible grid. If not, an experienced editor will look at it and say, ‘You know what? This has garbage entries.’” 

An example of a “garbage entry” might be something like the word OREO, which, as any cruciverbalist (or crossword puzzle expert) will lament, pops up frequently as an answer. Why is that? There are certain combinations of letters, says Ginzburg, that are “just really handy” for filling a grid. “Anything that involves low-Scrabble-score letters, lots of vowels, or odd abbreviations.” 

Most words in the English language, he elaborates, alternate consonants and vowels. “So, if you ignore consonant sounds that are made up with two letters, like CK, and you just think about single-letter sounds, in order to fill a square, you have to alternate words that start with a consonant or a vowel. So, in a crossword puzzle, you’re going to find more words that start with vowels than you would in ordinary text, and those words are going to be used more often. And that’s how you end up with words like OREO and ARIA being overused.” 

The number of venues for selling crossword puzzles has diminished over the years, says Ginzburg, partly because fewer people read newspapers. And although he has less time to devote to it, solving puzzles will always be a favorite pursuit for Ginzburg: “I enjoy it more now that I’ve had the chance to create a lot of puzzles and because I appreciate more the artistry that goes into them.” 

As father of a 7-year-old and a 5-year-old, Ginzburg also gets a kick from hearing them start to make puns and experiment with wordplay. “It’s like, ‘Yes! They picked up the gene!’” 

The crossword solution can be found here.