The puzzler and the puzzled | Feature | Chicago Reader

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The puzzler and the puzzled

In which our writer searches through, down, and across the history of crosswords for clues on constructing his own

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After I called Tausig for pointers on constructing puzzles, I went off to gin up some ideas. In a standard 15-by-15 puzzle, he said, ideally 40 squares, and at least 37, should be taken up by the theme. A general symmetry is desired: if one of the theme answers is 13 letters long, there should be another 13-letter entry to match it. And there should be at least three answers that correspond to the theme.

When filling a crossword grid, I suppose the old saw about writing what you know applies doubly—you're literally restricted by what you know, though cheating is allowed. (Having specialized software voids the question altogether. Tausig uses a program called Crossword Constructor, with the computer suggesting words to insert into the ever dwindling blank spaces. It comes with a word list that Tausig can add to.) Whatever's on the mind of a given constructor can affect the makeup of a grid, or the way that it's clued. In 2007 Bill Clinton was invited to write clues for a Sunday Times puzzle that had been built by constructor Cathy Millhauser, who clearly had the former president in mind when she filled the grid. The theme was baby boomers; Clinton supplied the clue "Boomer's update of a 1972 Carly Simon song?" to the answer YOU'RE SO VEINY. Of course Clinton has other well-known interests, and the puzzle also included entries for "Foreign lady friends" and "Those French girls" (AMIGAS and ELLES, respectively).

Ben Tausig, who writes the Reader's Inkwell crossword, may regret being publicly involved with the creation of the puzzle Chillinois
  • Ben Tausig, who writes the Reader's Inkwell crossword, may regret being publicly involved with the creation of the puzzle Chillinois

In Crossworld, Marc Romano notes the layers of cultural specificity in the solution to a vague clue like "2002 upset," which he found in a puzzle by wunderkind constructor Brendan Emmett Quigley, who in 2007 was accused by the Boston Globe of "making the New York Times crossword hip." The answer, SUPER BOWL XXXVI, he notes, requires the solver to know that, first, "Superbowls are numbered with Roman numerals and, second, that the thirty-sixth was an underdog victory pulled off by the New England Patriots." And that's sports. Everyone knows about sports.

Romano later finds out that Quigley, being from Boston, has an indigenous interest in the Patriots. He had also been watching the game while he built the puzzle.

What was I doing as I first attempted to build a puzzle of my own? As it happened I had just broken up with my boyfriend of three years, and so I was after the usual pursuits: listening to down-tempo music, drinking such whiskey that would make a cowboy blush, and reading textual analyses of the Elizabeth Bishop poem "One Art" on the Internet. The poem, a villanelle, is the one that starts out: "The art of losing isn't hard to master"; Bishop follows the casual, almost playful tone almost to the end, when she switches to the second-person and confesses that "losing you" is, finally, a "disaster." The effect is devastating. I started to wonder if I couldn't build a crossword around the poem's rhyme scheme, which involves the repetition of "-aster": vaster, faster, disaster.

Plus, here was a chance for a good Chicago reference—one would obviously want an answer to be PLASTER CASTER, as in Cynthia Plaster Caster, the local groupie who makes plaster molds of the penises of rock stars. What else? BROOKE ASTOR, the New York heiress who died a few years ago at age 104. Symmetry is important in crosswords (constructors also speak often of "elegance"), so I'd need another 13-letter entry and another 11-letter entry, to match what I had so far. I cycled through a few ideas: GRANDMASTER, as in Flash, or chess; GHETTO BLASTER, too racist; WITH DISASTER, as in flirting—too long. Finally SANDBLASTER, the graffiti-fighting tool, and NOW DO IT FASTER, a phrase that seemed colloquial enough, though at this point I suspect it wouldn't have made it past Ben Tausig's editorial pen.

I never intended to show him this one, though. I just wanted a little practice. I gave the finished product to a couple of coworkers, who both finished it. Tausig told me later that unless it was for a poetry magazine or something, the theme was "a bit too specific." In his book Gridlock Matt Gaffney talks about attempting to piece together an income by making themed puzzles for specialized magazines. It's not high art. "I once paid my rent by writing a tabbies-themed crossword puzzle for a cat magazine," he writes. "The clue for 18-across was 'It might flatten when tabby's angry' and the answer was EAR. Not quite Michelangelo at the Sistine Chapel, but the check cleared, and I could always hope that time would bring better things."

Margaret Farrar retired as the New York Times's puzzle editor in 1969 and was succeeded by Will Weng, who held the job until 1977. Of the four puzzle editors in the Times's history, Weng's tenure was perhaps the least remarkable—he wasn't a pioneer of the form like Farrar was, and he didn't refine and popularize it to the extent of the current editor, Will Shortz. Certainly he didn't have the chilling effect of his immediate successor, Eugene Maleska, a fearsome former Latin teacher. Maleska was a bane. His tenure was characterized by an overreliance on what cruciverbalists call "crosswordese," needlessly abstruse clues and answers that hinder solution of the puzzle more than they help. In Cruciverbalism, Stanley Newman supplies an example. Maleska would've looked favorably, he thinks, on "Fibre of the gomuti palm," the trickiest clue in Arthur Wynne's inaugural word cross. In the post-Maleska era the clue might have been different: "Homer Simpson exclamation." For both clues the answer is DOH.

Newman, a competitive puzzler, also began building crosswords during Maleska's reign at the Times, and had a serious ax to grind. He starts Cruciverbalism with an account of an event known as the LOA incident, which he variously calls an "outrage" and an "atrocity." Newman was upset that Maleska chose not to clue the answer LOA with reference to Hawaii's Mauna Loa, both traditional and a kindness to solvers; instead the editor clued it as "Seat of Wayne County, Utah," which, Newman notes, then had 364 inhabitants. "My apologies to the people of Loa," he writes, "but 'Seat of Wayne County, Utah' was a useless piece of information that made it into the Times puzzle solely because Eugene Maleska took a pedant's pleasure in flummoxing other people with obscure facts."

Newman also edited the Crossworder's Own Newsletter, a platform from which he "declared war" on Maleska. Not only were Maleska's puzzles esoteric, Newman thought, they were also "defective." In a newsletter feature called Keeping Up With the Times Department he pointed out each time the paper committed a "howler"—in his estimation, something like "issuing a puzzle with a theme that called for celebrities' last names that are also cities (JOHN DENVER, JULIE LONDON) but boneheadedly included a country (JILL IRELAND)." Newman wasn't alone in his distress over Maleska's pedantry. He represented a movement of puzzlers that came to be called the new wave—younger enthusiasts who wanted crosswords to be, if not exactly easy, then at least not larded with useless, alien information.

Maleska was vanquished not by Newman's newsletter but by death. He was replaced in 1993 by Will Shortz, who was born on an Arabian horse farm in Indiana and received a degree in "enigmatology." Since the 70s Shortz had been the editor of Games magazine and the founder and host of the American Crossword Puzzle Tournament, which brought competitive puzzlers together for annual competition in a hotel in Stamford, Connecticut. It was depicted in the 2006 documentary Wordplay, and has since moved to Brooklyn.

Under Shortz, the puzzle caught up to pop culture, or started to. Romano notes that Shortz also "radically reinforced" the policy of presenting puzzles in ascending order of difficulty through the week, with Monday the easiest and Saturday the most diabolical (Sunday's, a much larger puzzle, is supposed to be about on par with Thursday). A certain amount of crosswordese is unavoidable, which is why you see the name of Brian ENO so often in puzzles. Recently Matt Gaffney introduced a way to measure what he called the "Shortz Factor," which relates to how often a vowel-rich famous person's name appears in the Times. Others have calculated this honor not by frequency but by day of the week; the writer Sherman Alexie said that he's been pleased to watch his name appear earlier in the week as his star rises.

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