It happened this spring, in the 2012 Virginia Scholastic and Collegiate Chess Tournament. Both Quentin Moore and his opponent, a rising star on the D.C.-area chess scene named Clark Smiley, came into their match undefeated over the weekend-long competition. So the state title and an expenses-paid cross-country trip to the national high school championships would likely go to the game’s winner.

Judging by his pre-tournament rating — 2141, according to the U.S. Chess Federation system, making him the second-highest of the 75 players vying for the high school title — Moore shouldn’t have had any trouble getting past Smiley (1875). But Smiley was on fire, having won nine of the 12 previous rated tournaments in which he’d played and taken second place in the other three. Smiley’s former high school coach, forgetting that the kid’s spree came in state and regional events and not globally significant competitions, now says Smiley had put up “a record only Bobby Fischer could have.”

And in a match played in an earlier round at the Scholastic tournament, held at a Best Western in McLean, Virginia, Smiley had whupped Aravind Ponukumati, a teammate of Moore’s on the perennial state champion chess squad from Thomas Jefferson High School for Science and Technology. Smiley was rated almost 200 points below his opponent, but played “several hundred points above his rating,” Ponukumati says.

“He was playing so aggressive,” Ponukumati said. “I remember thinking, He’s crushing me!”

Against Moore, Smiley continued his dominance. For an opening, he played what pawnheads would describe as the Kevitz variation of the Queen’s Gambit Declined, a sophisticated attack for which Moore had no good answer. Smiley had Moore in check after 16 moves and never let up.

“I was about to resign,” Moore says.

Moore was too focused on just avoiding checkmate to pay much mind to Smiley’s off-board behavior. He ignored Smiley’s frequent tap-tap-tapping away on a handheld Dell computer. Smiley had been given permission to use the device to keep a digital record of each move — but only for that purpose.

“A lot of kids use those now, and I knew those were allowed,” says Moore of the scorekeeping app, called eNotate, which had only recently been sanctioned by the chess powers that be for tournament use. eNotate received the blessing of administrators after its designers convinced the USCF that the software was fail-safe for cheating. Moore, then an 18-year-old senior at TJHSST, generally regarded as one of the brainiest high schools in the country, shunned the gizmos in favor of an old-school record-keeping method: paper and pencil.

But while Moore ignored his opponent’s between-move activities, tournament director Robert Getty didn’t. Getty, who says he was aware of Smiley’s winning streak, monitored the match from across the ballroom. Its one-sidedness held his interest most.

“I’ve watched Quentin Moore play in these tournaments over the years,” Getty said. “He’s always been a strong player. And while I’ve seen him lose before, I’d never seen him take a beating like he was taking here. He was getting destroyed.”

And when he spotted something fishy about the way the player consulted his personal digital assistant, Getty moved in for a closer look. After Moore’s 28th move, Getty halted the match and asked Smiley to show him the PDA. Smiley pulled away and turned off his device, says Getty, but after several uncomfortable seconds he handed it over without saying a word.

Getty fired up the Dell again, and no score sheet appeared. Instead, a screen popped up for a program from the Fritz line of so-called “chess engines.” These are super-smart, user-friendly apps able to analyze the positions of all pieces on the chessboard and consider millions of possible outcomes in a matter of nanoseconds before suggesting the best next move. By pushing all the right buttons on a good chess engine, any Kardashian sister could conceivably checkmate Fischer.

And, as proven here, with Fritz’s assistance, Smiley could destroy Moore.

Smiley admitted to Getty and others that he’d cheated. While making his confession, though, Smiley said the game against Moore was the first and only time he had ever accessed the illegal program.

Smiley was ordered to forfeit that match and all previous games in the event, and was thrown out of the tournament. Despite the player’s unadvanced age, the Virginia Chess Federation used Smiley’s name in their announcements of the suspension, one sign of how seriously they are taking the offense. The federation quickly suspended Smiley for what was termed “using unauthorized software indicating an assessment of his position and analysis of possible variations.” His ethics case was referred to the national sanctioning body, the U.S. Chess Federation. According to USCF president Bill Hall, Smiley is, at 16 years old, the youngest computer cheat ever brought before his group.

He now faces a lifetime ban.

“He’s just a little boy who made a mistake,” says Catherine Smiley, his mother.

Clark Smiley, whose mother declined to make him available for an interview, was removed from his high school team. His neighborhood club, which had become the strongest and most hard-core chess clique in the D.C. area, had a civil war over the scandal; Smiley’s high school coach, distraught over what he said was a shaming of the game he loved, led a separatist movement and formed a new confederation designed only for “honest players.”

But even though the kid’s only confessed misdeed came among small-time players in an otherwise unremarkable tournament, the electronic score-sheet caper could have implications far beyond the hotel ballroom where it occurred. Most important for everybody but Smiley: Along with being the youngest techno-cheat, he is also the first player of any age caught exploiting an approved software application as part of a cheating scheme.

So folks at the USCF are now trying to determine exactly how Smiley cheated, and how often. The answers could affect not only the severity of his punishment, but the future of computers in competitive chess.

“This is all new for us,” says VCF president Andrew Rea. “This is a serious breach. We can’t just let it go.”

Gadgetry of any sort has a rocky history in chess.

In the late 18th century, for example, a Hungarian engineer named Wolfgang von Kempelen toured Europe with a machine called The Turk, which he promoted as a mechanical chess master. Legend holds that Napoleon and Ben Franklin are among the chess aficionados who lost to Kempelen’s brainchild. Decades after those big wins, word got out that The Turk, which Kempelen built to woo Empress Maria Theresa Walburga Amalia Christina of Austria, was a royal scam: For all its pulleys and wheels, Kempelen always made sure an accomplished and totally human chess player was hiding inside the machine, making all the right moves.

The Virginia scandal involved the opposite ruse, in which a machine surreptitiously called the shots for a player. The chess engines this scheme centered on are relatively new: Computers only surpassed humans at the chessboard during young Smiley’s lifetime. Scientists had an easier time designing digital brains that could produce atom bombs or navigate lunar landings than they did fashioning a machine that could play chess worth a darn. Plainly, until relatively recently, chess was too complicated for computers. An analysis of chess’s complicatedness in Wired determined that the number of possible positions in an average 40-move game is 10 to the 128th power, a sum “vastly larger than the number of atoms in the known universe.”

In 1966, MIT brainiacs entered MAC HACK VI, a computer program they’d devised, into the Massachusetts Amateur Chess Championship, making it the first computer program ever to enter a tournament. It drew just one match and lost four.

And it wasn’t until 1981 that any computer program beat a player with a master rating in tournament play. (Full disclosure: My brother, Geoff McKenna, who, despite being a chess master by rating and among the strongest players in the D.C. area, was never a threat to take Garry Kasparov’s crown, got written up in chess and scientific magazines in the early 1980s after defeating Belle, a product of Bell Laboratories and back then the reigning world computer chess champion.)

But by 2007, a chess engine called Rybka was routinely shutting out grandmasters even when spotting the humans a pawn and taking black, thereby letting humans go first, the more statistically desirable position. Computers have gotten noticeably better since then; humans haven’t.

The man-machine war in chess is no longer contested: “Computers are better than us,” says USCF president Ruth Haring.

Some old-school gamers lament humanity’s slippage. “Chess was more fun when computers were patzers,” says Peter Biyiasas, a former grandmaster and Canadian chess champion. Biyiasas says his decision to retire from competitive chess was helped along by the advent of superhuman electronic aids.

But Haring and other caretakers of the game have been pushing to increase technology’s presence. Without computer intervention, they fear kids who spend most of their days accessing one app or another would ignore the sport of kings (and queens and rooks, et al.). And some portions of the computer creep have inarguably been a boon — online chess, for example.

And as training tools, chess engines, including the Fritz software that Smiley depended on, are a godsend to the game.

“I grew up when nothing was computerized and you had to live in New York or San Francisco to get to play against great players,” Haring says. “You just played your neighbor. Now, you can train against a grandmaster-strength program, and all the openings of all the great players are available at your fingertips. There are all these tools that have really opened up the game.”

The dark side, of course, is that technology-aided cheating episodes have popped up all over the place in recent years.

Among the more entertaining techno-scams: In the 2006 World Open in Philadelphia, the most moneyed tournament in the land — this year’s event, which concluded in July, had a kitty of $250,000 — tournament director Mike Atkins got bad feelings about a competitor named Steve Rosenberg, entered in the 2000-and-under division (a category for competent but non-master players). Rosenberg came into the tournament having won 18 matches in a row. Then Rosenberg kept his winning streak going against superior competition in the early rounds of the World Open, all the while wearing several layers of clothing in the heat of the Northeastern summer and playing each game with his hands cupped over his ears. Atkins eventually surmised the oddball get-up was part of a scheme, and that Rosenberg was somehow getting moves fed to him. With Rosenberg undefeated heading into the late rounds of the tournament and one win away from taking home the $18,000 first prize, Atkins confronted him about his suspicions, and during the interrogation a tiny electronic device was discovered in Rosenberg’s ear. The player claimed it was a hearing aid; Atkins hopped on his laptop and from Internet research quickly found that the gadget, called a Phonito, was in fact a radio receiver that could be used to relay information from a third party, and, in this case, was likely a third party accessing Fritz or some other chess engine. (The $270 Phonito was manufactured by Phonak, a Swiss electronics firm that at that time was in the news as the sponsor of Floyd Landis during his Tour de France cheating episode.) Rosenberg declined to answer Atkins’s questions; given what was at stake, the tournament director took the non-answers as a confession and booted him out of the tournament.

“If you’re going to lose $20,000, you’d scream bloody murder,” Atkins told me in 2006. “Instead, he just said, ‘If you’re going to forfeit me, just give me my thing back and I’ll go home.’ And he left.”

Rosenberg has never been heard from again in competitive chess circles. (A caller responding to messages left at the phone number in Canton, Michigan, listed for Steve Rosenberg in old USCF directories said that though his name was Steve Rosenberg, he didn’t play chess.)

And not all the bad acting in chess takes place on our shores: In July, the World Chess Federation bounced three high-level French players for an elaborate cheating scheme from the 2010 Chess Olympiad in Siberia. Joanna Pomian, the head of the Fédération Française des Échecs, the French chess federation, dropped a dime on members of her own national team. She discovered that the French squad, led by 21-year-old grandmaster Sebastien Feller, was being fed strategy in the middle of games by coaches who were consulting computer chess engines. Pomian said she’d acted only after finding incriminating text messages sent between team members, including one from a player to a coach that read, in French, “Hurry up, send moves.”

A couple years ago, I spoke with Larry Kaufman, a designer of the Rybka software, regarded in recent years as the strongest chess engine on the market. I asked if he worried that his brainchild would be abused by bad guys. Never, he said.

“The cheating part isn’t hard,” Kaufman told me. “Getting away with it is. I don’t think chess players are good enough to get away with it.”

Smiley clearly wasn’t good enough to get away with his chessboard crime, though questions remain about how good a cheater he really was. His PDA was not confiscated after he was caught using a chess engine at the Virginia Scholastic. “I showed the PDA to [other tournament officials], who also saw the PDA running with the illegal software,” says Getty, “and after he’d admitted to cheating, I returned the device to the player. I had no right to keep it.”

That meant officials couldn’t perform an autopsy on the Dell to learn how often Smiley had accessed the program illegally during tournament play.

Catherine Smiley says she believes her son’s once-and-only-once version of his cheating timeline. She also says accusations of serial cheating are nothing more than “sour grapes from people he beat fairly.”

Sour grapes or no, it is true that all the evidence contradicting Clark Smiley’s contention that he only cheated against Moore is circumstantial.

It’s also pretty darn convincing.

Smiley’s tournament wins started coming in bunches in the summer of 2011, after he’d attended a camp sponsored by the Ashburn Chess Club. They take the game very seriously there. The Ashburn club only formed in 2009, but this year its teams took first place in both the Open and Amateur Divisions of the D.C. Chess League, one of the strongest confederations in the U.S. For Ashburn’s camps, international master Nikolay Andrianov serves as the lead counselor. The club charges members for sessions with Andrianov, a Russian native who commutes cross-country from his Phoenix home. He can command such a fee because of his 1978 win over Kasparov — meaning he’s one of the few to ever beat the greatest chess player of all time in his prime.

Understandably, Ashburn brass did an awful lot of patting itself on the back and cheerleading during Smiley’s winning streak. A solicitation for Andrianov’s clinics put out last year called Smiley “a model for scholastic players.”

“Clark Smiley did it again!” read a blurb in the club’s online newsletter from August 2011, after Smiley went 5-0 while winning last year’s Atlantic Open. Smiley took home $1,200 in prize money for that win.

“[Smiley] has improved tremendously since the Ashburn Chess Camp,” read the club’s newsletter after the Atlantic Open win. “Congratulations, Clark. You make us proud of your achievements!”

The USCF stats show a turnaround that sure does seem too good to be true. Before July 2011, Smiley’s career record as a tournament player was 180 wins, 151 losses, and 13 draws. But Smiley went 41-3-2 in the 46 official games he’d played heading into the Virginia Scholastic.

“Forty-one and three? That’s a record only Bobby Fischer would have,” says Dino Obregon, the faculty adviser for the chess team at Stone Bridge High School, the Loudoun County, Virginia, school Smiley attends and played chess for before being removed for cheating. “This kid isn’t Bobby Fischer. I beat him.”

The climactic match of the Atlantic Open came when Smiley defeated Bryan Simonaire in the final round. “That would have been my biggest win,” says Simonaire, who wasn’t aware that his opponent had subsequently been caught cheating until he was interviewed for this story. The news triggered some memories of the matchup.

“I remember talking to [Smiley] after our game,” says Simonaire, who away from the chessboard is a Maryland state senator and member of the Special Senate Committee on Ethics Reform. “My impression of this kid wasn’t Whoa! This is a tough chess player!, which is that attitude you often get from kids who can really play, kids who know the game. But he just seemed like a regular kid. I figured he had a good day.”

Asked what else he recalled about their match, Simonaire says, “He had some device in his hands the whole game.”

The USCF website allows a player’s ratings growth to be displayed in graph form. Smiley’s personal chart features a massive vertical hike in his rating beginning last summer. Robert Getty points out that Smiley’s USCF rating in so-called blitz chess, a quickie version of the game, is now 283 points below his standard tournament rating. And while winning nine of his 12 standard tournaments prior to the Virginia Scholastic, Smiley never won a blitz tournament. (Moore’s blitz rating stands only 77 points lower than his tournament rating; Ponukumati’s blitz-tournament differential is just -38.)

“That’s significant because in blitz you don’t keep score,” he says. “There’s no electronic score-sheet app for blitz.”

Getty is one of a large contingent of folks familiar with the Virginia scandal who believe Smiley’s cheating scheme lasted much more than just one game.

Adam Chrisney, a fellow member of the Ashburn Chess Club, is another. Just two weeks before he was officially caught cheating, Smiley won an event called the Virginia Open. Chrisney, also an entrant, says he found Smiley’s tapping away on his PDA in the early rounds of the event bothersome, but didn’t initially think anything ominous was taking place. eNotate’s novelty and reputation as being cheat-proof provided a great cover, says Chrisney.

“I knew that [electronic score sheets] were allowed, so I figured this was a kid using his new toy,” says Chrisney.

But when Chrisney had to face Smiley in the last round of the tournament with the Virginia Open title going to the winner, his opponent’s keyboard work no longer seemed harmless.

“It should take maybe three or four taps, max, to record a move on a score sheet,” Chrisney says. “He was making copious amounts of taps on the keyboard, and I really started wondering what the hell he was doing.”

Smiley whupped Chrisney in that game, but after the match Chrisney reported what he suspected was cyber-cheating to tournament director Mike Atkins — the same guy who blew open the Phonito cheating scam at the 2006 World Open. Atkins questioned Smiley, but didn’t find enough evidence to overturn the result. (Atkins declined a request to discuss the Smiley case for this story.) The win over Chrisney gave Smiley the tournament title and a $400 cash prize. Chrisney says his judgments were vindicated after Smiley was caught at the Scholastic tourney, but says the situation makes him feel bad for the perp.

“He’s a kid, and this isn’t murder,” says Chrisney, who would have won the Virginia Open had he beaten Smiley. “But cheating is bad for chess.”

Ponukumati is also convinced he was up against a computer when he was supposed to be playing just Smiley. Virginia Scholastic tournament rules prohibited players to leave the main room if they weren’t playing. While Moore was facing Smiley in the fifth round, Ponukumati was hanging out with TJHSST teammates in an adjacent room doing a postmortem on his loss to Smiley earlier in the event. Ponukumati says he plugged all the moves from the earlier game into various chess engines and “found a clear pattern of cheating.”

“Every move from moves 13 to 30 matched [the computer],” says Ponukumati.

Moore, with a question, offers perhaps the strongest argument that this wasn’t a one-off incident: “Why would he start cheating in the fifth round of a tournament?”

The failure to seize the Dell also means some mystery remains about Smiley’s cheating methodology. It’s unclear exactly how Smiley accessed the chess engine while ostensibly also running eNotate.

“This is the first time there’s been an incident reported with eNotate,” says Rea, “so there’s still a question about what was done so [Smiley] could enable other software applications on that device.”

The two options are:

1. Highbrow But Sneaky: Somebody hacked the eNotate program stored on Smiley’s PDA to allow the app to run concurrently with a chess engine.

2. Lowbrow But Brazen: Smiley simply turned off eNotate once a game started and ran the cheating program exclusively.

Moore, who will study computer science at the University of Virginia, isn’t ready to discount the possibility that hacking took place. He admits being daunted by the brainpower that would take, however. “I couldn’t do it,” he said.

Sevan Muradian, the designer and primary vendor of the eNotate software, asserts no hacking took place. The USCF rulebook specifically states that to gain tournament certification, vendors of electronic score sheets must prove that anybody using the score sheet “cannot access a chess engine or any stored games, openings, or analysis contained within the electronics of the device.” And, say USCF officials, eNotate passed muster. Muradian remains convinced it’s hack-proof.

“Once you enter recording mode of eNotate, recording the game, you cannot flip to another application. You cannot use any other program — not Fritz or any chess engine,” says Muradian. “We deactivate any wireless connection and disable any hardware buttons. [Smiley] didn’t override that. No way.”

Only “about 500” copies of eNotate, which sells for from $50 for just the software to about $150 for a loaded PDA, have been distributed so far. Each copy is registered with the North American Chess Association. The NACA website shows Clark Smiley’s father, Mark, registered as no. D866204. Registrants can authorize others to use their software in tournaments, according to Muradian.

Muradian says his own investigation of the Virginia Scholastic cheating episode leaves him convinced the player took the low-tech route to the low road and ran only the Fritz program while cheating. Of course, if it were proven that a high school kid could override eNotate’s firewalls through a hack, the software would likely immediately be banned from tournaments. Asked if his theories on what happened were colored by what was at stake, Muradian says no.

“There was no hack,” he says.

Even so, Muradian says he’s going to design new screens for eNotate that are “more annoying,” so tournament directors can more easily discern whether a player’s PDA is in fact running the sanctioned program. He thinks that’ll be enough to prevent copycat cheats.

The USCF has not said when it will announce a ruling on Smiley’s ethics case.

As for how the scandal will affect others: Moore will henceforth be wary of every PDA-equipped opponent he faces. “I’d played [Smiley] twice when he was using the handheld device, and he beat me both times, and once when he wasn’t, and I won that game,” says Moore. “But I had no reason at the time to suspect he was cheating. I’ll suspect everyone who uses these things from now on.”

Getty intends to keep a closer eye on players of any age who show up at the table using an electronic score sheet.

Haring says she’s troubled by the cheating episode, but has no plans to use it to launch a technological crackdown within USCF.

“Technology we can work with,” she says.

Haring ascribes her positive outlook to an incident involving (who else?) Bobby Fischer. In the early 1980s, Fischer, already well into his exile from the chess world and the real world, came to San Francisco to hide out and stayed with Haring, whom he knew through chess. And while there he came across a stash of paper score sheets from her playing career, all from long before the advent of Monroi and eNotate. “I kept all my old games in a shoe box in a closet,” says Haring, who was an international master as a player before entering a career in chess administration. “And I came home from work one day and saw that Bobby Fischer had found the box and had gone through all my games. I was terrified, but I asked him, ‘So, what do you think?,’ and he said something that helped me with the rest of my life. He said, ‘You’re a pretty good player, but you’re too pessimistic.’ He was right. And when Bobby Fischer speaks, chess players listen. So I use that as a general guiding rule in the rest of my life, too: Don’t accept a bad situation; look for ways to improve your situation. It helped my chess game and my life. It helped me to look for a positive, better outcome; there’s a better move there. So, technology, yes, there are threats, but it’s good for the game.”

The Ashburn Chess Club held another summer chess camp in August, led once more by Andrianov. The 2012 camp ended with an in-house tournament, with the winner receiving a trip to Russia to play against kids in the world’s chess epicenter. That’s a big prize. But, because of the actions of a former camper at last year’s gathering, a new rule was in place. The Ashburn website advised all prospective attendees that they would have to get through camp “without the use of electronic devices.”

“I like pencil and paper,” says Andrianov. “That’s what kids in Russia use, and it’s worked out pretty well for them.”