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Chapter 1

Hello, World

[Faux pas?], 6 letters*

—JOON PAHK, Outside the Box, 2020

The story begins with a baby, or at least the idea of one—it was 1989, summer in suburban Auburndale, Massachusetts, at the west end of leafy Newton along the Charles, most of the vinyl-sided homes keen to resurrect the analog witchiness of old New England by opting for gas lamps instead of streetlights, candles on the sill instead of electric overheads. Eric Albert and Peg Primak had decided to start a family. Peg, a manager at Bolt, Beranek and Newman (BBN, the R&D behemoth and precursor to Raytheon, the missile and defense technology outfit) was gifted at navigating the ecru nooks and crannies of corporate bureaucracy, and didn’t want to quit. Eric, who’d worked as a computer programmer for a decade and jonesed for something more independent (“I’m no good at being an employee,” he told me, “I think like an owner”), thought he’d try being a stay-at-home dad. In the meantime, he needed a new job—something he could do remotely, something more entrepreneurial—since New England homes and New England babies weren’t cheap.

In 1989, there were barely a million American stay-at-home dads (that number has since doubled), and about as many suburbanite workers who didn’t commute by car to an office park; the overlap may as well have been the null set. Eric was an outlier. As it happened, he was spending a few days that summer with a merry band of outliers, the members of the National Puzzlers’ League. Launched in New York in 1883, the League, which issues a riddle-riddled monthly newsletter named The Enigma, was founded “to provide a pastime of mental relaxation for lovers of word puzzles, to raise the standard of puzzling to a higher intellectual level, and to establish and foster friendships among its widely scattered members.” At the 1989 convention, in the lobby of a Cleveland hotel, Eric had an idea: he could become a professional crossword puzzle writer. He pictured sitting in his den, baby balanced on his lap, tax-deductible reference books fluttering open like manta rays, as he dashed off grids to editors he already knew from the League.

Eric canvassed his fellow conventiongoers. Collectively, as if referencing how their technicolor “recreational linguistics” might be for the mind what a Mardi Gras second line is for ear and eye, NPL members are known as the Krewe. Individually, members of the Krewe are known by “noms,” cryptic pen names inflected with festive wordplay or personal accents. Eric sought advice from Hex (the puzzle power couple Henry Rathvon and Emily Cox, colleagues at BBN), Double-H (Henry Hook, a surly, quick-witted Brooklynite known as “the Marquis de Sade of the puzzle world”), and WILLz (Will Shortz, a play on Will + “short” Z, then the editor of Games magazine; he would take over the Times puzzle editorship four years later). Photo captions from that year’s convention read like a yearbook from a Wookiee magnet school: “Back row: [. . .] Hudu, Ai, Grams, Qaqaq, Smaug, Faro, Blade, Alf, Sluggo, Ulk (behind Sluggo).”

So spoke the G(r)eek chorus: “Don’t do it.” To many of them, puzzling was a hobby, only that, and besides, everyone wanted their byline in the New York Times Arts & Leisure section, willing to suffer the slings and arrows of a freelancer’s pittance in pursuit of nerdcore bragging rights. The flood of submissions was one reason rates were so low: $15 to $75 for a 15-by-15-square crossword, the standard for dailies; $50 to $250 for a Sunday-sized 21-by-21. “Few people could grind them out quickly enough,” Eric wrote at the time, “to be able to afford both food and shelter.”

But maybe a computer could. Back then, crosswords were made entirely by hand. Graph paper, pencils, erasers; a miscreant’s penchant for puns; a mystic’s delight at serendipity—these were the tools of the trade. One constructor ordered specialized scratch pads stamped with 15-by-15 grids from a company in Maine. And when they needed a 7-letter word whose third letter was X, constructors might haul out a reference like The Crossword Answer Book, a doorstopping dictionary facsimile whose section headings were semi-filled-in strings, like neon signs with letters selectively dimmed and flickering: ?N?B??, ?N??B?, ??NB?? Form and function, as in any genre, followed material constraints. The prolific constructor Brendan Emmett Quigley—puzzledom’s punkest rocker, whose shock of red hair and warlock beard make him part Velvet Revolver frontman and part retirement-era David Letterman—has said he built countless grids in the 1990s centered around flashy 7-letter words, packed like sardines in a crossword’s corners; the reference book he owned didn’t go up to 8s.

When Eric returned to Newton from Cleveland, he cast around for existing crossword construction software, but there wasn’t much to speak of. Mary Virginia Orna, a chemistry professor at the College of New Rochelle, used her lab’s x-y plotter to print professional-looking grids, but it didn’t help construct them. The few commercially available programs produced only “criss-cross” lattice grids from user-supplied dictionaries, waffle-like puzzles where the words rarely crossed and that often lacked the canonical 180-degree symmetry of modern grids. Mel Rosen, a well-known puzzle maker, editor, and member of the Krewe (nom: Quip), sold Eric a copy of The Crossword Puzzler, a program he’d written for the IBM PC that helped enter, store, and retrieve clues; autoformatted numbered grids and clues for printing; and even boasted a nascent search mechanism, fetching words that matched a specific pattern of letters. It certainly softened the constructor’s burden. “But I didn’t want to make the job easier,” Eric wrote. “I wanted to make the job go away.”

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Eric was born in Boston in 1957. His mother was a biology professor with a PhD from Brown, an accomplished woman of science at a time when graduate programs still rarely admitted women. His father, a computer scientist, exposed Eric to math from a young age. By the time he was eight, Eric had memorized solutions to puzzles by the legendary Sam Loyd, a prodigal chess player turned “recreational mathematician”—that is, a practitioner of “mathematics uncontaminated by utility,” in the words of writer and mathematician Martin Gardner. Loyd’s “Famous Trick Donkeys” puzzle was used as a promotional item for (and later sold to) P. T. Barnum and his circus. (When Loyd died, in a kind of oedipal rearrangement, his son Walther changed his name to Sam, and continued his father’s work of producing puzzle books and toys.) Eric and his father would solve the Times crossword as a pair, announcing a clue number when one of them knew its answer, giving his co-solver a chance before writing it in.

In high school, Eric landed his first coding job. He did research for Edmund C. Berkeley, a computing pioneer whose 1949 book Giant Brains, or Machines That Think all but predicted internet search (“Suppose that you go into the library of the future and wish to look up ways for making biscuits. You will be able to dial into the catalogue machine ‘making biscuits’ ”) and email (before “going to South America for a year, we [will] see our address book as a spool of magnetic tape. When we wish to send out announcements, we put a stack of blank envelopes into the machine”). Eric would fiddle with the refrigerator-sized instruments after school, fussy and expensive enough that Berkeley kept them behind locked doors. Then on to Brown University, where he was an early beneficiary of the school’s Open Curriculum, which abolished core requirements and allowed students to take any number of classes Pass/Fail. Eric, who attended Brown at the same time that Talking Heads were forming just down the slope of College Hill at the Rhode Island School of Design, had a very 1970s undergraduate experience. Already a capable programmer, he opted for a BA rather than BS degree in the newly christened Computer Science department, just as the field—more abstract, more creative—was extracting itself from the blockier diktats of Electrical Engineering and Applied Mathematics. He made an impression on Andries “Andy” van Dam, the graphics pioneer whose mentorship, at Brown, of several future Pixar filmmakers is believed to be the origin of the Toy Story protagonist’s name. He ended up taking all his nonmajor classes Pass/Fail. He was the only man in a survey course on Lesbian Literature (he passed, he says, in more ways than one).

Outside of schoolwork, Eric and a close friend, Alan Frank, cowrote perhaps the first-ever distributed computer game. Eric had devoured one of the earliest teletype “interactive fictions,” in which players read preprogrammed text and responded with short commands, a limited number of which would move the narrative forward. The game was William Crowther’s 1976 Colossal Cave Adventure, a cross between Dungeons & Dragons and Crowther’s experiences exploring and mapping Kentucky’s Mammoth Cave, the longest cave system in the world. That story begins:

You are standing at the end of a road before a small brick building. Around you is a forest. A small stream flows out of the building and down a gully.

What’s next?

Alan and Eric built new functionality on an IBM 360 mainframe—“That was no joke,” he says, “that was real computer science”—so others could design their own levels in the game. Years later, after overhearing Eric’s name at a Brown reunion, a faculty brat turned game designer thanked Eric for his service; playing it, the man said, was the reason he’d gone into game design in the first place. Eric and Alan were also members of the university’s Scrabble club. A friend who owed Eric a favor unearthed a digital copy of The Official Scrabble Players Dictionary, and together he and Alan programmed a set of tools to give themselves a competitive edge. Their software spit out a list of the 7-letter words (bingoes, in Scrabble lingo) that, given the overall distribution of tiles and the existing board, were likeliest to appear on a rack.

After graduation, Eric and Alan decided to live together in Medford. Eric wended his way through a glossy hedge maze of software jobs, gigs that, come the full moon, revealed some Halloween-ish underside. He liked the technical work at BBN (he’d worked there too, as did Crowther; everyone did, they “basically invented the internet,” says Eric) but felt stifled under the fluorescent spotlight of management. He worked for a start-up run by three MIT professors that buckled under the founders’ corruption; one of the professors was John Donovan, a management guru whose high-priced, high-theatrical seminars earned him the nickname “the Johnny Carson of the training circuit,” and whose litany of misdeeds includes forged documents, a decades-long legal battle over one of his son’s fortunes, and falsely claiming another son hired Russian hit men to assassinate him. (He was saved by his belt buckle, he said, which had magically deflected the bullets, leaving just a flesh wound in his stomach.)

After all that software mishegas, computer programming for pay came to remind Eric of the Sherlock Holmes story “The Red-Headed League.” In it, a pawnbroker with red hair is handsomely paid to copy out the Encylopaedia Britannica—numbing, fruitless clerical work, meant to distract while criminals pilfer a bank nearby. It was not the income-generating but the recreational tinkering that lit up Eric’s circuits, and soon he would train his algorithmic gaze on a problem that served as a precursor to computer-generating crosswords: word squares.

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Word squares are crossword fossils, grids of letters arranged so the same words can be read horizontally or vertically. Chisel swapped for pencil, an answer key in search of clues, they have the eerie, extraterrestrial heft of Stonehenge or crop circles. The best-known specimen is the Sator Square, a 5-by-5 Latin creation first discovered in 1936, carved into a stucco column in the ruins of Pompeii’s Palestra Grande, dateable to before 62 CE:

S A T O R

A R E P O

T E N E T

O P E R A

R O T A S

Read row by row or column by column, the square offers the same palindromic message: SATOR AREPO TENET OPERA ROTAS, “The sower Arepo holds the plow.” In the centuries to come, the sentence became a kind of counterspell; one imagines flapping black robes, slits of etched letters brimming with orange light. In the fourteenth century, it is said, the square could quench wildfire; in the fifteenth, it cured the insane. To many, the crossed palindrome at its center, TENET (“he holds”) represented Christ; the sower might have been a reference to the parable of the sower, in Matthew 13. The square has been inscribed on the walls of abbeys and chapels, scratched into amulets and books, a lexical mandala tattooed the world over by mystics and paranoids. Around 1830, a Dutch doctor in Pennsylvania included the inscription in a medical manual, the block-letter engraving of Pompeii traded for inked manuscript cursive as florid and witchy as the flick of a wand. Patients were instructed to write the square on a piece of butter bread, then consume it, as a cure for rabies.

Late in the twentieth century, Eric and his friend Alan were methodically furnishing word squares of increasing scale, tracking their progress like rock climbers advancing from V2s to V5s. They’d worked their way up from 3-by-3s you could fill off the top of your head to 7-by-7s requiring a dog-eared Oxford English Dictionary nearby. Everest, to them, was the 9-by-9. As far as they knew, the first 9-by-9 square in history had appeared on December 28, 1897. Constructed by Arthur F. Holt (“the master formist of his time,” beamed Eric), the square ran in the Chicago Inter Ocean “back when newspapers were enlightened enough to carry that sort of thing.”