The New York Times Crossword Puzzle Still Stumps After 80 Years

New York Times, crossword
It used to be a major challenge to try and solve the Sunday puzzle in pen. These days, lots of people solve the puzzles online or electronically. Flickr (CC BY-2.0)

If you don't enjoy solving crosswords, your friends or coworkers, parents or grandparents might. It's relaxing, fun to do alone or with a buddy, and research shows it's good for your brain. Pushing 80 years old, The New York Times daily crossword in particular is an American institution.

Strangely enough, The New York Times was the last major metropolitan daily newspaper in the country to start a crossword. When the crossword puzzle craze gripped the United States in 1924, the paper publicly condemned the fad, publishing a scornful editorial in which it called crosswords the "latest of the problems presented for solution by psychologists interested in the mental peculiarities of mobs and crowds." Which was a pretty sick burn back in 1924. Simon and Schuster published the first crossword puzzle book that year, and most American newspapers started a crossword between 1924 and 1926. The holdout of The Times might have had something to do with the fact that it had never done comics or entertainment features of any sort — the fun stuff was considered frivolous by its editors.


But the crossword had staying power, and at the beginning of World War II, Arthur Sulzberger, the editor of The Times, decided it was time for the paper to start its own puzzle.

First Editor Was a Woman, Margaret Farrar

"The probably apocryphal story is that Sulzberger was tired of buying the competing New York Herald Tribune to get their crossword," says current New York Times crossword editor Will Shortz. "It was the start of World War II, and it was thought that people needed to take their minds off the grim war news. So, The Times had the good sense to ask Margaret Farrar to be the crossword editor. She had co-edited all the Simon and Schuster crossword books going back to the very first one in 1924. Margaret immediately raised the quality of the crossword above anyone else's — the intellectual calibre of the puzzle, the cultural references and just the quality of the puzzle-making: more interesting vocabulary and fresher, more on-target definitions."

Farrar was The Times crossword editor for 27 years, from 1942 to 1969, and the puzzle evolved a bit over that time. At the start, she was given the directive that the puzzle should reflect the information the reader was picking up in the pages of the newspaper — so if you go back to those early puzzles, you'll see a lot of war references. But Farrar thought the crossword should distract people from the harsher aspects of life, which is why, over time, she began to include more entertainment, literature and non-news subjects.


Farrar was succeeded in 1969 by Will Weng, who was the head of the Metropolitan desk at The Times before he took the job of crossword editor. Weng was an old-fashioned news man, but had an abiding love of crosswords — he had been creating puzzles for The Times for years before he became editor.

"His greatest innovation for The Times crossword was humor," says Shortz. "He was genuinely a funny man and his sense of humor came through in the puzzles. Weng retired in 1977 and was succeeded by Eugene T. Maleska. I'd say the wordplay in the crossword themes became more varied and sophisticated under Maleska — it became more a word game than in previous years. But Maleska was a staid guy — he had been a school superintendent in the Bronx, he loved opera and classical music and his puzzles had a more serious tone than Will Weng's."


Will Shortz, Current Editor Extraordinaire

Shortz became crossword editor in 1993 when Maleska died, and one of his goals has been to modernize the puzzle — to include more current cultural references, more up-to-date language and more playful themes. And the audience has broadened under Shortz:

"It used to be you'd think of crosswords as being mainly for older people, and I think that was true before I became editor. I can tell how the audience has broadened just by the people who contribute to the puzzle."


In the whole history of the puzzle before Shortz became editor, only six teenagers had gotten puzzles published in The Times. In Shortz's 25 years as puzzle editor, he has published 37 teenagers and lots of 20- and 30-somethings. The average age of contributors has come down by about 15 years — from the early 50s to the late 30s. The youngest person Shortz has published was 13, the oldest person was 101.

"It's an extremely diverse group of people who make The Times crossword," says Shortz. "It reflects The Times readership itself."

Shortz, you might have gathered, does not construct the puzzles himself, though he does create variety puzzles — unique and new variations in crosswords. Shortz and his two assistants get between 75 and 100 puzzle submissions each week, which they look through, cull to select the best ones, then edit for publication.

These days, most crossword puzzles have themes, which means the long answers tie together in some interesting way. When making a puzzle, you put your theme answers in a grid first, plotting black squares around those, which divides the grid into sections, which are then filled with words. When you've polished the puzzle to the best of your ability, you write the clues.

The Times crossword gets more difficult as the week progresses: Monday is the simplest, and the puzzle turns up the heat a little each day until the Saturday puzzle, which can seem nigh-on impossible. The Sunday crossword is bigger, but as far as difficulty goes, it's like a hard Wednesday or easy Thursday. Sunday is the biggest circulation day of the week, so Shortz wants to make sure the crossword is accessible to the broadest possible audience.

When Shortz started his job in 1993, virtually all the puzzles were created by hand on graph paper, and all of them were solved with a pencil (or pen, if that's the way you roll, hotshot). These days, most crossword constructors use computer software to build their puzzles, and lots of people solve the puzzles online or electronically.

"You have to subscribe to solve the online version of The Times crossword — even if you subscribe to the printed or online versions of the paper, you have to pay extra for it," says Shortz. "These days 430,000 people subscribe to just the crossword. It's become a significant source of income for the company."