“I don’t know. I think if I were you, I’d probably challenge the word ‘jomama.’ That’s just me.” Such was the conversation wafting over from the table behind us at the 2012 Scrabble For Cheaters tournament. Held at the headquarters of 826NYC in Brooklyn’s Park Slope neighborhood, this event is in its fifth year of raising money to foster the creative writing talents of area youngsters. It’s a single-elimination team tournament, and normal Scrabble rules apply. Except when they don’t. 

Scrabble For Cheaters codifies the mantra of the late, great professional wrestler, Eddie Guerrero—“Cheat 2 Win.” Cheating—like art forgery or, say, cat burglary—is generally frowned upon. When skillfully executed, however, these shady pastimes can elicit a grudging admiration, even in their victims. For years, Dutch art forger Hans van Meergeren enjoyed a heroic reputation for having fleeced Nazi official Hermann Goering with fake Vermeers. When 12-year-old Jeffrey Maier reached over the fence and plucked a baseball out of the air during 1996 American League Championship Series, he forever changed the destinies of both the Yankees and the Orioles. Maier was later awarded a key to the city of New York by Mayor Giuliani.

At 826NYC, it’s about breaking the rules to help the kids. (Of course, isn’t that what they all say?) I arrived at the competition through the doors of the Brooklyn Super Hero Supply Co., which looks like a bodega frequented by Ant Man. The shelves are stocked with products like capes, secret identities and cybernetic hench-fish. But the store itself is in disguise—it is a front, of sorts, supporting its 826NYC alter ego, a nonprofit center for tutoring and creative writing located in the back of the store. Kids are lured in by the retail zaniness, and before they know it, they’re learning despite themselves. 

The original 826 outpost, 826 Valencia, began in San Francisco as a pet project of the Pulitzer Prize finalist author and bleeding-heart polymath Dave Eggers. The quirky, successful concern—a writing center for kids aged 6 to 18 in San Francisco—spun off into different cities under the umbrella of 826 National. 826 is reliant on community fundraisers like Scrabble For Cheaters to bankroll its educational endeavors.

Prior to the tournament, teams raise money, which can then be used to buy “cheats” on game day. Cheats range from a single tile exchange ($50) to the wholesale invention of a new word that can be place on the board, no questions asked ($500). Others allow players to use foreign words (the “passport” cheat, $50) or to reject an opponent’s word out of spite ($250).

“You can win by raising a lot of money or being a really good Scrabble player,” said 826 NYC Executive Director Scott Seely, “but typically if you have a lot of cheats, that will win.” The cheats and their corresponding values have evolved over the years. The passport cheat, for instance, used to be $250, but this year it was reduced to $50. The cheater’s market had spoken. 

“We had someone make a judge cry two years ago.”

Notable teams this year included Game Of Thrones’ Peter Dinklage and playwright Jonathan Marc Sherman (“Overall Wash”); comedians Michael Showalter and John Hodgman (“Hodgwalter”); and the mother-daughter author team of Meg and Hilma Wolitzer (“Like The Judds, But Different”). Most believed that the team to beat was the non-celebrity tandem of Morgan Clendaniel and Gideon Friedman. “The Fightin’ Caziques,” as this cheating juggernaut is known, had won the tournament three out of the last four years, crushing their high-profile opponents with Ray Leonard-esque combos of cheats and tiles. When they arrived, these everyman champions brought with them the freshly polished Cheater’s Cup, to be awarded to this year’s winners.  

Scrabble players take cheating seriously. At the 2011 World Scrabble Championship in Poland, a minor scandal erupted when one player accused another of hiding a tile and demanded that he be taken into custody and strip-searched. Even Scrabble For Cheaters isn’t immune to underhanded tactics. Seely recalls the tournament’s first year, when someone casually swiped a tile off the table. “We caught them, and called them out on it. They denied it to the end. Scrabble junkies can get pretty intense. We had someone make a judge cry two years ago because it got so heated.” 

Emotions were more subdued this year, but there were moments of affected hysteria. Showalter and Hodgman are both veterans of Scrabble For Cheaters, but neither has ever won the coveted Cheater’s Cup. Showalter is an alumnus of the ’90s MTV sketch comedy show The State and the 2001 cult classic film Wet Hot American Summer. Hodgman is a writer and actor known for, among other things, playing the resident deranged millionaire on The Daily Show. Hodgman perhaps channeled this financial acumen to make Hodgwalter one of the tourney’s top fundraisers, but he didn’t disappoint in the derangement department, either. Heads turned when he suddenly removed his shirt and started flexing in the middle of a game. Whether this was an act of physical intimidation, psychological warfare, or lexicographical despair remains unclear. 

Maybe it was all three. Scrabble For Cheaters nullifies much of a good Scrabble player’s skills. The world’s best Scrabble player would be hard-pressed to win an honest game against the rule-benders at 826NYC. As one half of the cheat-poor, spirit-rich Team Gameological, I can attest to this personally. Our first-round opponents, The Lexicons, had raised some $700 and change. The laggards backing Team Gameological, on the other hand—having signed up mere hours before game time—failed to mobilize a timely fundraising push. Thanks to our sole sponsor, Gameological contributor Joe Keiser, we weren’t left completely defenseless. Early on in the game, I used one of our two cheats to add 10 points to a letter, which gave us the lead. Briefly.

Our game was close, at least. We overheard someone from another table going on about how their opponents made up four words. That’s $2,000 worth of cheating. “Team Annyong” spent time between rounds purchasing more cheats, discussing strategy, and playing Scrabble on their phones. One of Team Annyong’s players, Mehal Shah, can be found on the Internet sharing the art of “fighting dirty in Scrabble.” Another player, Amy Stephenson of “A Squared,” won on Jeopardy! last January. Exuding confidence, she shuffled tiles around on the board while wearing a jaunty hat.

Dinklage and Sherman faced the Caziques in the quarterfinals. Writer Sarah Vowell (who is on the 826NYC board of directors) presided as a judge. The game was a tense affair, a war of cheat attrition reminiscent of the steroid-era home run race between Mark McGwire and Sammy Sosa. Dinklage complained of a rotator cuff injury that may have been inhibiting his word deployments, and the champs eventually dethroned Overall Wash by playing the all-powerful create-a-word cheat. The gibberish they put on the board is apparently pronounced “snow.” 

Dinklage offered none of the normal platitudes of the defeated—nothing about giving 110 percent or leaving it all out on the field. “You’re catching me right after we got creamed,” he grimly informed me. “I’m filled with rage. Scrabble For Cheaters has nothing to do with real Scrabble. They’d be dead if we played them for real.” In George R.R. Martin’s brutal world, this would probably mean putting his opponents’ heads on spikes and pasting Scrabble tiles where their eyes used to be. Fortunately for the Caziques, the Emmy-winning actor is a little more forgiving than his character, Tyrion Lannister.

Their opponents made up four words. That’s $2,000 worth of cheating.

It was Dinklage’s fourth year playing in the tournament, and he credited Vowell as being “one of those people that can get you off your duff to things like this.” It also helps that Dinklage is a self-proclaimed Scrabble head. “I don’t do any games but word games. Friends don’t hang out with each other anymore,” he lamented. “Remember when we used to play social Scrabble? It’s just so rare now. So I just play Words With Friends on the iPad. It’s the only game I ever play. I used to play video games, but I’m too old for video games now.” I asked him what he used to play. “I’m the Atari generation, man. Missile Command was my jam.”

As I get older, I find that I’m less slavishly devoted to the purity of original rules. I still don’t like the designated hitter, but I’ve accepted its existence as something that must be tolerated in good humor, much like Farmville or athlete’s foot. Before 1973, when the rule was instituted, many baseball fans felt that letting a position player hit for the pitcher is tantamount to cheating. That view remains among baseball purists, but over the years the DH has become accepted as part of the baseball’s idiosyncratic world. Games like Scrabble For Cheaters or Words With Friends vulture the parts that they need from the original and jettison the rest, feeling free their own dynamics and adherents. I’m not suggesting that everyone should jam a Scrabble tile down their pants for a rainy day, but a bending or occasional breaking of the rules is a healthy step in the natural evolution of a game.

Words by Drew Toal. Illustrations by Richard Hofmeier.