Can Garry Kasparov stay a move ahead of Vladimir Putin?

Perhaps the greatest chess player ever, the former world champion has become a fierce critic of Vladimir Putin's Russia and an advocate for freedom around the world.

In February 2013 the Investigative Committee of Russia gave Garry Kasparov's 76-year-old mother a call. They were looking for her son.

Kasparov had been one of the nation’s brightest lights for decades. In 1985, at 22, he became the youngest winner in the history of the world chess championship. He was suave and cocky, a virtuoso, and he captivated the chess-mad U.S.S.R., where every world champion became a household name. He is widely considered the greatest player ever. Twelve years would pass, and the Soviet Union would fall, before he lost his first match, and even then he remained ranked No. 1 until his 2005 retirement, when he abandoned chess to become a political activist.

Russian president Vladimir Putin had been running the country for only five years, but already Kasparov saw the nation hurtling backward. Kasparov and his compatriots called for fair elections; instead Russia held votes that were presumed to have been rigged. The more Putin clamped down—silencing dissent, eliminating enemies—the more urgent Kasparov’s mission became. In 2007, he was jailed for protesting and then denied the opportunity to run for president. (Putin’s comment on the arrest: “Why did Mr. Kasparov, when arrested, speak out in English rather than Russian?”) Then, in 2012, Kasparov was arrested and detained while protesting the imprisonment of the dissident feminist punk band Pussy Riot. A Russian court acquitted him soon after on the charges that he bit an officer. But still the Investigative Committee, Russia's equivalent of the FBI, wanted to have a chat.

“They ‘invited’ me,” Kasparov says, “to be questioned as a witness in one of the many political cases they were investigating.” For guidance he called his friend Boris Nemtsov, another opposition leader. Nemtsov told him, “Garry, you enter the building as a witness, and if you exit the building, it's as a suspect. Stay away.”

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Kasparov by then was spending most of his time in New York City. Now, more than four years later, he has yet to return to Russia. He lives on Manhattan's Upper West Side with his wife, Daria, and their daughter, Aida, 11, and son, Nikolas, 2. (He has another daughter and son from two prior marriages.) He crisscrosses the U.S. and Europe as chairman of the Human Rights Foundation, which promotes democracy around the world.

As for Nemtsov? He was gunned down in Moscow in 2015, hours after he spoke in support of a protest against Russia's war in Ukraine. “I wish Boris had followed his own advice,” Kasparov says.

According to Akhmed Zakayev, a Chechen leader in exile in Great Britain, Putin and Chechen dictator Ramzan Kadyrov resolved after protests in 2012 to punish four major opposition leaders: Alexei Navalny and Sergei Udaltsov would be jailed, and Nemtsov and Kasparov would be killed. Kasparov notes that indeed Navalny and Udaltsov were sentenced to prison terms, and Nemtsov was killed—“so maybe it’s a real story.”

Kasparov has even been getting an unusual question at book signings recently: Why aren’t you dead? To these queries he replies that at this point, his death would only negligibly burnish Putin’s strongman credentials; he has already made his point.

As the grandmaster sees it, Putin reached a point in early 2014 where he had run out of moves domestically. “You need confrontations with the free world to stay in power [in Russia],” says Kasparov. So Putin invaded Ukraine and annexed Crimea. Although the new territory bolstered his neo-Soviet reclamation project, retaliatory sanctions from the West manacled the Russian economy. (A coincidental collapse in the price of crude oil had already jeopardized Putin's agenda.) But Putin, pressured to retreat, chose instead to counterattack. He increased Russian involvement in Syria, casting his country as the courageous enemy of ISIS.

The menace Putin posed troubled Kasparov enough for him to publish a book, Winter Is Coming, his first nonchess title, in 2015. In it he likened Putin’s past decade to Hitler's 1930s, and he fingered Bill Clinton, Barack Obama and Gerhard Schröder as latter-day Neville Chamberlains.

As with most every Hitler comparison, it struck some as hyperbolic and alarmist. Well, it did back then. “I tried to tell people that winter was coming, and they didn't want to hear it,” Kasparov says. “Now people all want me to tell them to be afraid.”

Kasparov was reminded recently of his 2015 book-tour appearance on Bill Maher’s HBO talk show. Maher told Kasparov to wake him up when Putin invades Poland. Kasparov says it took all he had not to jump up and down on his chair. “Well,” Kasparov says now, “it seems as though he skipped over Poland and went straight to Wisconsin.”

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Kasparov is a man of many theories—that’s all they are, theories—but they’re shaped by years of tussling with Putin, and untainted by any great yearning for President Hillary Clinton. (Kasparov’s American political hero is Ronald Reagan, thank you very much.)

“In Putin’s eyes, Trump was the perfect counterpart,” he says. “The way Trump views the world is all about doing business, about deals.” Kasparov figures Putin aspired to approach Trump with the deal of all deals: “NATO, the EU, who gives a damn? Let’s redesign the map; you’re FDR, I’m Stalin. Maybe we bring in Angela Merkel, or the president of China—we’ll be the new Big Three. Equals! Who cares about Estonia, Latvia, Syria? We’ll play the game. Mmm, for Trump, that’s music to his ears!”

How would such a deal get done? Who would even be able to put it in front of the president, knowing that it contravened American doctrine and would not make it through the ranks of career foreign service officers at the State Department?

That, Kasparov says, is where Michael Flynn came in: “I’ve been saying from Day One that he was compromised.” Former acting attorney general Sally Yates says she told the White House in January that Flynn was vulnerable to Russian blackmail. Kasparov says Putin must have figured Flynn would quietly advance Kremlin interests.

With Flynn in control of the national-security apparatus and in back-channel communications with Russia, and with Rex Tillerson, a Russia-friendly dealmaker, atop a threadbare State Department (nearly 200 posts stood empty as of late April), all the pieces had fallen into place. Putin had influenced the U.S. election and now he could do the same to U.S. foreign policy.

But in early February, top-level government sources leaked to The Washington Post that Flynn had discussed with Russian ambassador to the U.S. Sergey Kislyak the possibility of lifting sanctions Obama had placed on Russia, and then had lied about it to FBI agents. Four days later, Flynn was fired.

Kasparov's protest of the Russian government's policies in 2012 earned him the same global fame his chess championship had decades before :: Lisa Kessler/AP

Politicians and commentators have long treasured chess as a metaphor for diplomacy. (Even Trump: “You can’t terminate [multilateral pacts]—there’s too many people, you go crazy. It’s like you have to be a grand chessmaster. And we don’t have any of them.”) It’s not a bad metaphor, as metaphors go: Diplomacy, like chess, offers multitudinous but not limitless options for moves and countermoves, and rewards careful evaluation of your position and your opponent’s.

When Kasparov rose to prominence, though, chess was not just a geopolitical metaphor but a vehicle for geopolitics itself. The game has always been thought of as a relatively pure measure of intellect, and the presence of a Soviet atop the world rankings signaled to the empire’s subjects, no matter how poor and starving they may have been, that they possessed some sort of superiority.

An unbroken run of Soviets had held the world championship from Stalin’s tenure to Brezhnev’s. Then came Bobby Fischer. A decade before he beat then champion Boris Spassky in Reykjavik in 1972, a 19-year-old Fischer had alleged in Sports Illustrated that the Soviets had fixed international tournaments and conspired to deny him a shot at the world title for the sake of propaganda. (They almost certainly had.) But he eventually did conquer Spassky.

Anatoly Karpov claimed the title in 1975, when Fischer’s mania prevented him from defending it. And Karpov still held it in 1984, when Kasparov came calling, determined to remake the image of the Soviet chess superstar as the U.S.S.R. itself was loosening up. Karpov was an ethnic Russian and a Communist Party darling; Kasparov was, in his words, “a half-Armenian, half-Jewish menace to this good Russian boy.” His attacking style also contrasted with his predecessors’.

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Their first match took five months—and never ended. Karpov led five games to three (there had been 40 draws) when chess authorities called it off, ostensibly to protect the health of the players. (Kasparov contended that Soviet powers had prevailed upon the chess federation to suspend it before Karpov blew the lead.) The 1985 rematch in Moscow, contested under modified rules to prevent another marathon, saw Kasparov win 13–11. Kasparov won again in ’86, and drew in ’87, retaining his title.

Kasparov characterized the matches then, in SI, as a “battle between democracy and totalitarianism.” In Playboy, in 1989, he complained about the U.S.S.R.’s sexual repression, its government and “the Soviet chess mafia.” He threw his support behind the incipient pro-democracy, pro-capitalism movement.

And what happened to him? Nothing. “Because of my chess success,” he says, “I was untouchable.” That was no way for a Soviet to talk. But he was untouchable, and he had had unprecedented success, beating Karpov again in 1990. What more was there left for him to do in the chess world? The answer would come in the form of a humble “science experiment” backed by the sixth-largest company in the world.

It is unfortunate that a great many people happen to know Garry Kasparov—the pro-democracy crusader and probably the best chess player ever—as the grandmaster who lost 20 years ago to a computer.

After all, Kasparov had beaten two of that computer’s forerunners, and had he played up to his usual standards, he says he would have beaten the computer in 1997 too. He makes this clear in Deep Thinking, his new book concerned primarily with artificial intelligence writ large but which also provides Kasparov's first extended commentary on his loss to IBM's Deep Blue.

In the book he writes about the machine's handlers with the sort of spite usually reserved for dreaded rivals: “Secretive and antagonistic ... IBM wasn’t only building a chess machine to beat me at the board, but a machine to beat me, period.”

At the dawning of computer chess, grandmasters could easily tailor their games to machines’ obvious strengths and weaknesses. Carnegie Mellon researchers predicted in 1957 that a computer would beat the human champion by 1967; they were 30 years off. Computers understood chess mathematically rather than intuitively, which meant that while they could thrive in the middle game as pieces were strategically traded, they would struggle elsewhere. Computers simply lacked the processing power to see as far ahead as humans.

Then again, unlike humans, they never lose focus. And by 1997 the machines had gotten stronger and closer to victory—Deep Blue I had taken a game from Kasparov in their match the year before. Even so, to hear Kasparov tell it, he initially saw nothing sinister in IBM's request for a rematch once the machine had been suitably souped up. He thought it'd be a pleasant rivalry that would challenge (and enrich) both sides.

He was wrong. Kasparov and his team were denied access to records of games Deep Blue had played to train for the rematch, though he had received them before the first match. The machine had been taught human ploys, including pausing before making moves it knew it wanted to make. IBM hired several more grandmasters than Kasparov was aware of to stuff the machine with opening moves chosen for their particular effectiveness against him. Some of this value was lost, though, because Kasparov didn't play like himself in the Deep Blue matches—he switched to a style he thought would accentuate the computer's limitations.

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The world descended on the 35th floor of the Equitable Center in in midtown Manhattan that May to observe the match. Newsweek's cover had christened it, The Brain’s Last Stand. Kasparov won the first game but lost the second, resigning in anger, he writes, after being "so concerned with what it might be capable of that I was oblivious to ... how badly I was playing."

The knife was twisted a day later when a member of Kasparov's team told him that at the time he resigned, certain of defeat, the match had actually been a draw. The subsequent "shame and frustration made it nearly impossible to play." They drew the next three games.

Kasparov would lose Game 6 in humiliating fashion; it was the fastest game he had ever lost and the first time he had lost a match, ever. Kasparov made an early move—an unusual variation on a canonical opening, one that commentators roundly condemned as an unthinkable blunder—that he figured, nay, he knew, would trick the computer into retreat. Instead Deep Blue attacked. Kasparov's position was fatally compromised, and he became catatonic.

In a 2009 interview quoted in the book, one member of the Deep Blue team, Miguel Illescas, said that they had programmed that very override the morning of the match. Illescas also said—while maintaining that there was no connection—that IBM had hired a Russian-speaking guard to watch Kasparov during the match. Kasparov writes, "I will not repeat here the stream of profanities in Russian, English and languages not yet invented that escaped my lips when I first read that paragraph.... Am I alone in failing to make the leap of faith required to believe that the timing of this could possibly be innocent?" Kasparov does offer space to another member of the Deep Blue team, who says that the override was put in a month before the match, not during it.

Before he retired, Kasparov would finally lose to a human, Vladimir Kramnik, in October and November 2000, and then to Karpov. But nothing vexes him more than the loss to the machine followed by its immediate retirement from the sport. "I still have hard feelings," he says, "but now we can look at this event as a part of history. From my first loss to Deep Blue in 1996, that was it—from then on there was a clear path to machine superiority."

Adam Nadel/AP

Machines and their coming domination of the U.S. labor market prompted a lot of pondering after the 2016 election, and Deep Thinking's upbeat futurism is grist for that mill. Kasparov imagines man-machine hybrids pushing the U.S. toward staggering productivity in as-yet-undiscovered areas. He is fond of discussing elevator operators: how they remained long after the arrival of push-button technology only because riders were accustomed to them.

Estimates are that automation will displace 38% of U.S. workers over the next 15 years, but the Trump Administration is unconcerned: Treasury Secretary Steven Mnuchin said in March that job loss due to mass automation was "not even on [the administration's] radar screen" and was 50 to 100 years away.

Such denial of the coming upheaval, not the upheaval itself, is what concerns Kasparov most. "Machines won't make us obsolete," he says, "but our complacency might."

Yet Kasparov is heartened by what he has observed since Trump's election. "He has brought a lot of people into the political process," Kasparov says. "He has shown that American institutions are more resilient than we thought. I'm optimistic." And hey, if the guy who lost to a computer and spent years in Putin's crosshairs can still smile—why shouldn't we?