You have to be good to grab the attention of renowned puzzlemaster Will Shortz.

SPOILER ALERT!  This week’s post is about a crossword puzzle that I created and submitted to The New York Times.  For the most satisfactory reading experience, I advise you to attempt to solve the puzzle first.  To do so, you will need to download the free Across Lite crossword application.  If you’re a fan of the NYT Crossword, you’ve probably already done this.  Next, download my crossword puzzle in Across Lite format.  You’ll be able to tackle my puzzle on your computer, or you can print it out and have at it with a pencil.  Either way, good luck!

The summer of 2009 became the Summer of the Crossword Puzzle for me.  As a teacher who works according to the traditional school calendar, I have the luxury of indulging my interests every June, July and August.  What’s more, as the father of two active girls who participate in a variety of summer activities, I am often sitting poolside during a swim practice or waiting for the morning’s cross country training to end.  Short of good conversation with a fellow human being, I have found that a decent crossword puzzle is an ideal way to pass idle time.  It’s also a wonderfully engaging distraction from the dull concerns of everyday life.  That summer, the crossword puzzle rose in my estimation from a mere diversion to a worthwhile pursuit.

Key to my conversion from a casual solver to an enthusiast was the understanding that not all crossword puzzles are created equal.  There was a good reason why certain puzzles had been exasperating to me:  they were filled with crosswordese, the arcane vocabulary of obsolete little words that are used almost exclusively by struggling puzzle constructors simply to make a crossword work.  Even the most esteemed crossword of them all, that of The New York Times, was once guilty of this under the stewardship of former puzzle editor Eugene T. Maleska.  His legacy of impenetrable obscurities was quashed by current Times puzzle editor Will Shortz, whose philosophy leans toward making crossword puzzle solutions more dependent on wordplay than trivia, and what trivia there is should be universal rather than local.  In shortz (I apologize for that), a good crossword puzzle is challenging yet accessible.

I became a fan of the NYT Crossword, relishing its increasing difficulty as the week progresses from Monday through Saturday.  I read all the books I could find about the history of crosswords and the state of cruciverbalism today.  And then, on a whim, I printed out a blank 15 x 15 grid and gave a whirl at constructing one of my own.

My first effort gave me immense pleasure upon its completion, especially as it took me a full working day to construct.  Its theme was an in-joke intended solely for the amusement of my brothers, and therefore it was suitable only for a very small audience.  However, the mere fact that I was at all capable of crossword construction emboldened me to try something that might be appropriate for publication.  In a moment of great, swaggering bravado, I resolved to aim no lower than the pinnacle of puzzledom:  The New York Times.

The first task was to decide upon a theme.  I toyed around with words and phrases related to various interests of mine, keeping an eye out for anything that would work well on a standard daily crossword grid.  Nothing worked to my satisfaction.  Then I wondered, how about a Monty Python puzzle?  I soon discovered, to my delight, that the phrases MONTYPYTHONS and FLYINGCIRCUS were both 13 words in length, suggesting major thematic answers that could symmetrically offset each other. 

Next I entertained the notion of inserting the last name of each of the Pythons into the puzzle. John CLEESE and Terry GILLIAM have rather inflexible surnames.  I would have to clue them by referencing the men themselves, but at least I could use any of their well-known solo works.  Graham CHAPMAN could be clued with Johnny Appleseed, Terry JONES offered plenty of possibilities, and Eric IDLE is an actual word.  As for Michael PALIN, the spectacular Q  Score of a much-parodied Republican vice-presidential candidate was a true gift.  I went about setting all six of the Pythons and the name of their television show into my grid.

In general, it’s considered bad form to show off your cleverness by trying to wedge a very large number of thematic answers into a single 15 x 15 puzzle.  I already had eight of them at this point.  Still, I wondered if I couldn’t bury a few more Pythonic references among the fill (the letters that make up a puzzle’s solution).  LIFE would be related to two Python films, Life of Brian and The Meaning of Life.  Well, why not toss BRIAN and MEANING in there as well?  BBC, Python director IAN McNaughton, Palin’s IT’S catchphrase and BRITS found their way into the grid as well.  That put me at a rather silly fifteen thematic answers.  Even so, it bothered me that I made no mention of Monty Python and the Holy Grail.  Every way I worked it, even after multiple drafts, I could place neither HOLY nor GRAIL within the puzzle.  Then it occurred to me to hide it within bonus anagram circles.  What could be better than to finish the puzzle by finding THEHOLYGRAIL?  When I discovered that I could place the circles in such a way as to maintain the symmetry of the grid, I was in heaven.

Today’s puzzle constructors create their fill by compiling enormous databases of words and phrases from a which a computer chooses whatever fits the grid.  Not having this luxury, I consulted puzzle-solving websites that would list every possible word that is, say, five letters long with the fourth letter being K.  It helped enormously, but I eventually had to resort to a little crosswordese.  There was IBA, which I discovered was an acronym for Britain’s defunct Independent Broadcasting Authority.  ROA  is a  little bit of accounting jargon that stands for Return On Assets.  And then there was ALEO, which I didn’t think I could clue by referencing the Zodiac.  Finally I resorted to a bit of local trivia:  it happens to be the name of an Italian restaurant in New York City.  Well, if you’re going to be local in The New York Times, keep it in the Big Apple, right?

I massaged my puzzle until it was as good as I could make it, got some feedback from family members willing to try it, and revised a few clues.  Finally, I thought I had something worthy of consideration by the esteemed Mr. Shortz.  Then, conveniently yet coincidentally, I discovered that a momentous day in Python history was looming.  October 5, 2009 would be the 40th anniversary of the first airing of Monty Python’s Flying Circus.  The Pythons themselves would be in NYC to mark the occasion.  It was now early August.  There was no time to lose.  I assembled all my materials, carefully followed the submission guidelines, and mailed my puzzle to Will Shortz on August 5, hoping there would be enough time for it to be evaluated, accepted, and ultimately published on the great Pythonic anniversary.

Weeks passed by, and the enthusiastic response I hoped to receive did not come.  I envisioned my puzzle being passed along to Shortz’s inner circle for testing by top cruciverbalists.  Maybe contributors didn’t even hear yea or nay before their puzzles were published.  As October grew closer, I nursed a dim hope that I might see my very own puzzle appear in the Times sometime during the week of the 5th.  Alas, the optimum window for publication came and went.

On the Sunday before Thanksgiving, I finally received a message from Will Shortz in my inbox:

Hi Robert,

This is Paula Gamache writing, helping Will with correspondence.

Will says thanks, but must send regrets on your “What’s All This, Then?” 15x, whose theme didn’t excite him quite enough.

Sorry about that.  Will did appreciate seeing this, tho.

Best regards,


I exhaled a sigh of disappointment and pondered submitting my puzzle to another publication.  I still thought it was a decent crossword, if not Times-worthy.  As I mulled over my options, I remembered that the Monday Times puzzle was already available for downloading, as is the custom on Sunday evenings.  I printed it out so that I could solve it with a pencil, which I prefer over the computer.  It wasn’t long before my face twisted into an ironic smirk.

What was the theme of the New York Times crossword on Monday, November 23, 2009?  It concerned a certain group of lads from Liverpool.  Hidden within the fill were the four first names of The Beatles.