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A History of Crosswords

I've spent half a century writing for radio and print (mostly print). I hope to still be tapping the keys as I take my last breath.

It’s surprising to learn that crossword puzzles are only about 100 years old. You imagine a grizzled monk in his unheated cell in the 13th century labouring over an illuminated manuscript trying to trick his fellow holy men into using the wrong Latin word. Having been duped into writing “canis” for four-legged beast instead of “equus,” Brother Wilhelm slinks off plotting revenge. But no, we have to thank, if that’s the right word, Arthur Wynne for inventing the crossword in 1913.


The First Crossword Puzzle

The New York World ran a weekly puzzle page entitled “Fun” in its Sunday edition. Its creation was entrusted to a British immigrant called Arthur Wynne.

For the Christmas 1913 issue of the newspaper, Wynne invented something he called a “Word-Cross Puzzle.” It was a diamond shape of boxes with clues to the words that had to be filled in. The word FUN was already in place across the top.

Wynne was adapting simple word games that had popped up in 19th-century England and had been created for children. His grandfather had taught him how to solve “word squares,” as they were called, as a child.

The Word-Cross was immensely popular and became a regular feature of the “Fun” page.

While readers loved the new mind teasers, typesetters hated them. They were notoriously difficult to get right in the composing room. Inevitably, typographical errors plagued the puzzles, and at one point the title of the game was transposed and became “crossword.” The name stuck.

Wynne played about with a variety of shapes and finally settled on the rectangle.

The Crossword Craze

Briefly, The New York World toyed with dropping the crossword but wisely listened to the counsel of its readers who threatened subscription cancellations.

In 1924, a young man fresh out of Columbia University was trying to get a toehold in the publishing industry. He spotted the popularity of crosswords and he and his business partner went to the newspaper with a proposal. They offered to buy the rights to selected crosswords for $25 each and to publish them in a book.

The publication was a screaming success and sold more than 300,000 copies in its first year. It provided the seed money for Richard L. Simon and M. Lincoln Schuster to start what is now America’s largest book publishing company.

The popularity caused a spike in dictionary sales. Fabrics with black and white squares were turned into dresses and shirts.

The Broadway hit musical Games of 1925 produced a hit song “Crossword Mama, You Puzzle Me.”

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Crossword Rules

Over time, the organization of crossword puzzles became codified. Although it is now considered the gold standard of U.S. crossword puzzle creators, The New York Times long held itself aloof from what it called “a primitive form of mental exercise.” It wasn’t until February 1942 that The Times succumbed; here are a few of the conventions that apply to its crosswords:

  • The grid is symmetrical. The pattern of black and white squares is the same if the puzzle is rotated through 180 degrees.
  • A general guideline is that black squares should occupy no more than 16 percent of the puzzle. There should be no large blocks of black squares.
  • All words must link up with other words.
  • Two-letter words are frowned upon by aficionados; words should be at least three letters long.
  • No section can be cut off from the rest of the puzzle by black squares.
  • No words can be repeated in the same puzzle.
  • No naughty words are allowed.

The Cryptic Crossword

The first American crosswords tended to focus on general knowledge and word definitions. Great Lake (Erie) gets many a compiler out of a tight corner who has run into a shortage of vowels. Likewise Jai Alai and Oreo.

When the craze crossed the Atlantic and landed on the desks of English newspaper editors it took an evil turn. Enter the cryptic crossword.

Finding a synonym for unclear (5) no longer did the job. Thanks to people who love to play around with words, puzzlers can now be confronted with a clue that reads “Fashion that would be indefinite with a substitution for nothing” (

The keys in this convoluted clue are “Fashion,” “Indefinite,” and “Nothing,” and these are supposed to lead you to the answer. So, fashion conjures up haute couture, style, chic, and, if you are really lucky, vogue.

Indefinite might suggest unclear, confused, or dubious. But, if a moment of divine inspiration strikes, you might think of the indefinite article “a.”

Nothing can be zero or naught and represented by the letter “o.” Substitute “o” with “a” as instructed by the clue and vogue becomes vague, a synonym for unclear.

It is for this kind of linguistic chicanery that the witness protection program was created.

Leaked Secrets During Wartime?

In the month prior to the D-Day landings of June 6, 1944, a remarkable series of secret code words for the attack appeared in The Daily Telegraph’s crossword puzzle. “Utah” and “Omaha,” two of the landing beaches, and “Overlord,” the code name for the entire operation appeared as answers to clues. Other code words such as Mulberry (artificial harbours) and Neptune (the navy component of the assault) appeared just days before the landings.

The high command went into a panic thinking that someone was leaking secrets. Military intelligence arrested two crossword compilers but, after interrogation, decided the men were innocent.

However, a school headmaster, Leonard Dawe, was one of the creators. He was in the habit of inviting schoolboys to fill in crossword blanks as a mental exercise. Some of the boys mingled with Allied soldiers where they picked up the code words that were being freely bandied about. They then got inserted into Mr. Dawe’s crosswords.

Bonus Factoids

  • In 1924, The Times of London huffed and puffed in dudgeon about the popularity of crosswords. It called them “a menace because it is making devastating inroads on the working hours of every rank of society. Everywhere, at every hour of the day, people can be seen quite shamelessly poring over the checker-board diagrams, cudgelling their brains for a four-letter word meaning ‘molten rock’ . . .” The Times resisted the popular wave until 1930 when it published its first crossword.
  • One of the main forces in the creation of cryptic crossword puzzles was the British school master Derrick Somerset Macnutt. Understandably, he operated behind a pseudonym, probably to protect himself from angry mobs who found his puzzles so fiendishly difficult that they wished to do him harm. Appropriately, he compiled his puzzles under the name Ximenes, a Grand Inquisitor of the Spanish Inquisition.


  • “Two Girls, One on Each Knee: The Puzzling, Playful World of the Crossword.” Alan Connor, Penguin Books, November 2013.
  • “Basic Rules.”, undated.
  • “The Best of the Best of Uncle John’s Bathroom Reader.” Bathroom Reader Institute, July 2008.
  • “Beginner’s Guide to Solving Cryptic Crosswords.” Sandy Balfour, The Guardian, May 3, 2010.
  • “D-Day Crosswords Are Still a Few Clues Short of a Solution.” Val Gilbert, The Telegraph, May 3, 2004.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2018 Rupert Taylor


Liz Westwood from UK on December 29, 2018:

This is a fascinating article. I always assumed that crosswords had been around for longer than this. I was amused at the fumings of The Times, especially given that their crossword is now so well known.

Ellison Hartley from Maryland, USA on December 27, 2018:

Cool article! I'm no good at crosswords, I'm more of a word search kind of girl!

Pamela Oglesby from Sunny Florida on December 27, 2018:

I have never thought about when crosswords puzzles were created, so I found this information very interesting. I enjoyed the videos also.

Rupert, Have a Happy New Year.

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