UW News

December 10, 2009

Tax law and crossword puzzles: Being creative within restrictions

An avid crossword-solver, UW tax law professor Sam Donaldson was looking forward to working the puzzle in the back of his in-flight magazine on a recent trip. To his disappointment, it was a puzzle he’d already solved. In fact, it was one that Donaldson had constructed himself and was first published in the New York Times.

Any fan of crossword puzzles knows how addictive they can be, and the puzzle bug bit Donaldson as a child. He was as an avid reader (and solver) of Games magazine puzzles and his father solved the newspaper crossword puzzle every day.

“As a child, I would peer over his shoulder as he worked the crosswords, and occasionally he’d ask for my help with the clues,” said Donaldson. “I realized later that I don’t think he ever really needed my help.”

A few years ago, Donaldson watched Word Play, a documentary about crossword-solvers and constructors, and was intrigued with the American Crossword Puzzle Tournament featured in the film. He attended the 2008 event to celebrate his 40th birthday. Stressing that he doesn’t consider himself good to enough be truly competitive (“I was ranked 492 out of 699 contestants”), Donaldson said the weekend “was better than I could have ever hoped.”

“The contestants were all very friendly, warm, wonderful people. Even though crossword solving tends to be a solo activity, entire families came to the tournament.”

At the tournament, he talked to other contestants about constructing crosswords. They had recommendations for books and software and on the flight home, Donaldson wondered “Could I be good enough to get a puzzle in the NYT?” When he returned to Seattle, he started to construct his first puzzle.

Constructing crossword puzzles is just as complex as the puzzles themselves. They cannot have more than 78 words of at least 3 letters in length. The words must be recognizable. The grid can have no more than 38 black squares and, for English crossword puzzles, must have 180-degree symmetry (meaning they look the same upside-down as they do right-side up). Words used in clues cannot be found in the answers. And, a good puzzle has a clever theme. For NYT puzzles, the difficulty of the puzzle increases later in the week, meaning a Wednesday puzzle is harder to solve than a Monday puzzle, with Saturday’s puzzle being the most difficult.

Donaldson says he is drawn to puzzles, especially the construction of word puzzles, for much of the same reason he was drawn to tax law.

“Crossword constructors are like tax lawyers: you are limited by a ton of restrictions, but yet you have to have the ability to be creative within the existing set of very strict guidelines. You have to come up with things that work,” he said. They also share the love of words and the complexity of the English language.

“I don’t have the word smarts of most puzzle constructors, but I enjoy the impact each word has on a puzzle. Even the clues make creative use of language.”

Donaldson said the first puzzles he created and submitted were “horrible,” but he kept at it. After several of what he calls “thanks, but no thanks,” letters, Donaldson received a direct reply from none other than Will Shortz, the crossword puzzle editor of the NYT (referred to in Word Play as the Errol Flynn of Crosswords).

“He said, ‘I like this one, but can you fix one corner of the puzzle?'” Donaldson reworked it and, after a few more tweaks and bits of advice from Shortz, he was informed his puzzle was accepted for publication.

“The tricky thing about having your puzzle published in the NYT is you never know when exactly it will appear. They’ll tell you ‘It’s a Tuesday puzzle,’ but it could take up to a year for it to be published.”

On Thursday, October 2, 2008, Donaldson performed his daily routine of turning to the NYT crossword puzzle in the newspaper. After answering the first clue, he was dismayed to find the answer for 1A was the same as 1A for his own puzzle that he submitted. It was when he went to the second clue, however, that he realized this was his puzzle — it turns out that Shortz had slightly changed his 1A clue.

So far, the NYT has published two of Donaldson’s puzzles (the second appeared Wednesday, June 3, 2009) and accepted another four for publication. Law School Dean Emeritus Ron Hjorth, a friend and colleague of Donaldson’s, is also an avid crossword solver. Hjorth popped his head into Donaldson’s office after solving his second published puzzle with this advice: “Don’t quit your day job.”

When he’s not working on or creating puzzles, Donaldson directs the law school’s masters program in tax law and teaches a number of tax and business law courses. He’s popular with law students, who voted him Professor of the Year in 2002, 2004, 2006 and 2008. By student request, he also holds the honored role of auctioneer at the law school’s biggest fundraising event, the annual Public Interest Law Association auction.

As for Donaldson’s first NYT published puzzle, that later appeared in his Delta Sky Magazine, Donaldson admitted to making a few trips up and down the airplane aisles to see who was working on his puzzle.

“Wouldn’t you know it, they were all busy working the darn Sudoku!”