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Chapter 1

My Puzzling Problem

I am hopelessly addicted to the New York Times crossword puzzle.
Like many addicts, it's taken me time to admit I have a problem. The hints I was heading for trouble came, at first, only occasionally. The moments of panic when I realized that for whatever reason I might not be able to get my fix on a given day. The toll on relationships. The strained friendships. The lost hours I could have used to do something much more productive.

It gets worse, too. The high no longer lasts as long as it once did; what initially could occupy me for a whole afternoon now takes me twenty minutes or less to get through. I have become increasingly alarmed that the supply of the thing I need is limited. The Times publishes only one puzzle per day, and when that's done I find myself rooting about for substitutes--the Wall Street Journal, Philadelphia Inquirer, and New York Sun puzzles, to name just a few--that are somehow less satisfying. Sure, there are a couple of thousand puzzles in the Times's electronic archive. But a puzzle you've already done being something of a dead letter, falling back to that recourse is something like accepting an herbal cigarette when you're a smoker plumb out of Camels. There is no substitute for the genuine article, and a sort of panic sets in once it's no longer available. To badly paraphrase the British novelist C. S. Forester, it is prospect and not possession that affords the greatest pleasure, and the delicious agony of the twenty-four hours between completing one puzzle and starting another makes up the circadian rhythm by which my life has been regulated for nigh on two decades now.

If you've ever been to or listened in on a meeting of any of the twelve-step groups--Alcoholics Anonymous, Narcotics Anonymous, Overeaters Anonymous--you may have noticed the pattern that emerges from the narratives of the people who get up to publicly confess their addictions. These men and women all seem to be describing, in their own ways, how they were caught blindside by their particular object of desire. At an AA meeting, it may be the woman whose parents owned a tavern; all those surreptitious sips of liquids from colorful bottles as a little girl transmuted, for her, into a spiral of inebriation and promiscuity that ended only six months before in this very room. At an NA meeting, it may be the regional salesman whose toots of cocaine on the road, originally just to help clear his head, paved the way for divorce, petty theft, and finally grand larceny and imprisonment.

What these stories say, in essence, is that all addicts go through a lapsarian event of some sort or another, which may be why so many twelve-step meetings take place in churches: It's comforting to explain one's own fall from grace in an environment where the fact of being out of grace is dwelt upon so constantly. Addicts seem to fetishize the fact of their own fall, even though the process of falling is, in the end, rather the same whether you happen to be the reformed floozy, the now reemployed and sober salesman, or Adam and Eve. Only the substance changes: alcohol, cocaine, knowledge of good and evil. Or crosswords.

My own fall was right down the pipe, in addiction-narrative terms. Along with a few friends from my hometown at the northernmost end of Boston's North Shore (white-clapboard public buildings, preppies, gulls wheeling in the deep, snug, boat-filled harbor), I was invited down to New Canaan, Connecticut, for a house party hosted by a friend of ours whose parents had, the year before, moved from the Bay State to the Nutmeg State. This was late summer 1985; I was between my sophomore and junior years in college. The six of us drove down in two cars at far too great a speed, with me at the helm of a Ford F250 pickup whose nervous owner sat beside me, constantly doling out advice about the way I was handling his beloved truck.

Apart from the nagging, which occurred both on the way down and the way back up (and which I resented from someone who not only regularly treated his friends to hundred-mile-an-hour dirt-road horror shows, but who also needed me to do the piloting because the Commonwealth of Massachusetts had suspended his license for drunken driving a month before), it was really a perfect weekend. New Canaan was in its late-summer torpor, the hired band was unexpectedly decent, the cold beer flowed, and our friend's new Connecticut crew was so much like we six in thought, dress, and background that everyone seemed to have known one another for ages. We had, in short, a ball.

I went to bed late but woke up, as I generally did then and still do now, early. No one else in the house was stirring except the mother of the family. When I appeared in the kitchen, seeking coffee after a dip in the pool, she said the newspaper hadn't appeared and wondered if I'd be good enough to pick one up at a store in town (or village, really, at the time).

"Or two," she added. "With so many of you kids in the house, someone else is bound to want another magazine."

I drove into town and bought, as specified, two copies of the New York Times. When I returned, coffee was ready, no one as yet had emerged from the bedrooms upstairs, and my friend's mother was dropping a celery stalk into a Bloody Mary. With a grunt of thanks, she took one of the papers, extracted from it the New York Times Magazine, and flipped it open to the puzzle page.

Then she sipped her drink, examined the black-and-white grid, and set to work. The house was silent but for her sipping (Bloody Mary), my sipping (coffee), and the rapid-fire scratching of her pencil. I didn't know yet that it's perfectly acceptable in Times-buying households to say nothing to a houseguest, even if the guest is your daughter's and not your own, until you've finished at least half the puzzle and a Bloody Mary.

Feeling vaguely offended, I reached for the spare magazine out of sheer retributive spite. The next moment, I became a puzzler.

This is not to say that I'd never done a crossword before. I had, in spades: the Boston Globe puzzle, most of the time, or the puzzle in TV Guide, or any other puzzle one picks up at moments when one needs distraction. The one common denominator is that they were easy, pastimes rather than challenges, so at the time I preferred reading to puzzling. I still do, except for when a fresh Times puzzle is to be had.

Ten minutes later, my friend's mother mixed herself another Bloody Mary and returned to the kitchen table. After maybe another twenty minutes, she sighed contentedly. Then she mixed herself a third Bloody Mary and rummaged through the other sections of the paper. My coffee was cold and barely touched and I'd completed less than a third of my puzzle when the daughter of the house appeared, with the other houseguests more or less in tow, if two hours later counts as "in tow." My friend said good morning to her mother and then drifted over to ask me how I was doing with the crossword. I grunted by way of answer. I had begun, you see, to understand.

I couldn't believe that a New Canaan matron with two stiff prebreakfast drinks under her belt had managed to complete the same puzzle I was working on a full three hours before I did. I was at least thirty years younger than she and the lazy salutatorian of my high school graduating class--and a second-year student at Yale, for God's sake, even if an unmotivated one. My performance was shameful.

When I finally did finish, barely minutes before we were all due to drive home again, and after having spent several hours skulking around the house, avoiding the presence of people who wanted to "help" with the puzzle, I glanced at the top of the page to see who was responsible for it. The only hint that it had not been constructed by Satan himself--that there was a human agency behind the puzzle--was the single line, "Edited by Eugene T. Maleska."


Maleska Versus Shortz

That name "Maleska" imprinted itself upon my brain at once and forever. It was an odd-sounding collection of syllables: odd-sounding in the sense that it echoed any number of East European names whose possessors had bedeviled me up to then with their machinations physical (Erno Rubik), literary (Ernst Kantorowicz, Mikhail Bakhtin), and scientific (Dmitry Mendeleyev, cursed be all chemistry).
"Fine," I thought to myself as we piled into our cars. "Fine, Eugene T. Maleska, from this day onward, you'll publish no puzzle but that I'll complete. Eugene T. Maleska, you probable Slovakian evil genius, from this day on your ass is mine."

In truth, from that day on, the ass-ownership situation was the other way around completely. Eugene T. Maleska had possession of my puzzler's soul from that day in August 1985 until he died in 1993; I mourned his passing the way someone else might mourn the closing of a favorite corner restaurant--with a sense of grief partly admixed with an anticipatory dread of what new institution might come to take the departed one's place.

Many others, over the ensuing years, were also to mourn Eugene T. Maleska. A former teacher of Latin and then administrator in the New York City school system, he was an iconoclast and, some had it, a world-class curmudgeon, famous for developing instantaneous and permanent grudges against crossword constructors who violated any of the myriad iron (but never actually spelled out) rules he seemed to believe governed the world of puzzles. Yet he had built up an ardent following of people who agreed with him that puzzles should mainly concern themselves with high culture and disdain words or phrases that had originated since roughly 1960. If you knew the names of opera stars, the titles of popular songs from the 1930s and '40s, and which horses had won the Kentucky Derby in the first half of this century, you stood a fair chance of completing any crossword the Times published under Maleska's tenure, which began in 1977. If, like me, you didn't have this body of knowledge to hand--or if you were unfamiliar with Maleska's favorite filler words, such as "adit," "oryx," "ani," and "esne," among a dozen or so others--you were forced to rapidly develop a working understanding of both the references and the vocabulary. If you were of a certain age or a cultural snob or raised in or around New York City (or, ideally, all three), he was your hero: You knew what to expect from the crossword that would appear on your doorstep the following morning, and you could be reasonably certain you'd eventually finish it. In a sense, consistently solving Maleska's puzzles made you an honorary New Yorker, back when New York was Ed Koch and not Rudy Giuliani or Michael Bloomberg.

All that changed when Maleska went up, in 1993, to that big crossword grid in the sky. The puzzle's new editor, a person named Will Shortz, had a very different understanding of what a crossword should be, and, for the effect he would have on me as well as on literally millions of other puzzlers, he turned out to be a far, far more baneful figure than his predecessor. Largely this is due to the fact that Shortz is a much cleverer puzzle editor than Maleska or his predecessors, Margaret Petherbridge Farrar and Will Weng (my deep apologies, Eugene T.; you were fun while you were around, and I do still miss you). Shortz is also a more technical, more engaged, and more democratic puzzle editor than any of his forebears.

What the words "clever," "technical," "engaged," and "democratic" mean when applied to crosswords is an indication of the changes Shortz was to bring about in the august institution of the Times puzzle (which began running every Sunday as of 1942 and daily as of 1950). For now, the words "fiendish," "difficult," "evangelic," and "irksome" can stand in for them. But the point, again, is that the old Times puzzle used to demand of its solvers little more than a general body of knowledge acquired over a lifetime spent in the United States from about 1935 to about 1985. This is not to say that Maleska's puzzles weren't difficult enough. Under Will Shortz's direction, however, the puzzle began to demand much more extensive knowledge of contemporary culture, plus the ability on the would-be solver's part to come to terms with a number of other puzzle dimensions: themes that bear on how one interprets clues correctly, rebuses, squares containing more than one letter or figure, graded levels of difficulty, and so on.

Perhaps the most significant change instituted by Shortz was radically reenforcing the policy of scaling puzzles by difficulty, with the week's easiest appearing on Monday and its hardest on Friday or Saturday. (Although larger than the weekday crossword, Sunday's is usually, in terms of difficulty, at about the Thursday level.) For many, including me, this meant it soon became almost pointless to pick up a copy of the New York Times on Monday or Tuesday, since the puzzles appearing in them were constructed with the beginning or inexperienced solver in mind and, in a noncompetitive context, simply weren't worth doing. For many other people, this time not including me, it also soon became pointless to pick up Friday or Saturday's, either, since their difficulty upped the frustration factor manyfold, causing legions of faithful crossworders to abandon a particular puzzle for perhaps the first time in their lives. And, needless to say, to curse this interloper who had ruined the classical crossword experience so carefully nurtured by Maleska.

Even Shortz's name seemed an ill omen, since all his predecessors had sounded, or at least on the printed page looked, more imbued with gravitas than he. Margaret Farrar (nae, and for a while editing puzzles as, Margaret Petherbridge, which sounds like a character out of Wodehouse) had echoes of Farrar, Straus and Giroux and serious books; the unusual moniker of the Times's second puzzle editor, Will Weng, didn't bring any specific image to mind, but that odd combination of Western-sounding first name and Asian-sounding last certainly caught the eye. "Eugene T. Maleska" is of course a showstopper, evoking images of scholars poring over massive tomes in the lugubrious silence of the Slavic Reading Room at the New York Public Library. By contrast, "Will Shortz" sounds like someone you'd meet in the cattle-feed section of a farm-supply store in Indiana.

Shortz was in fact born in Indiana, and when you meet him in person he's every bit as warm, open, enthusiastic, and friendly as you'd expect someone from the Hoosier State to be, but that's about where the whole expectations-met game comes to a shuddering halt, Shortz-wise. Sometime around 1960, when he was less than ten years old, he fell in love with puzzles. After a couple years of practice, he sold his first one for publication when he was fourteen. He entered Indiana University as an economics major, but soon realized the school had an independent-study program that allowed a limited number of students to design their own major. He applied and, as every press piece on Shortz since has reported, he convinced the docents to grant him an undergraduate degree--the only such degree granted by any university anywhere, ever--in the field of enigmatology, or the study of puzzles and games and their relationship to the cultural environment in which they are created and solved. After college he went to law school, and for a while it seemed that, his unusual undergraduate concentration aside, Shortz was headed for a career that would raise no eyebrows in his Indiana hometown.