Subscribe to Off Message on Apple Podcasts here. | Subscribe via Stitcher here.

Chess? That’s not what Garry Kasparov sees Donald Trump or Vladimir Putin playing—three-dimensional or any other kind. But if they did sit down for a game, the former grandmaster believes the Russian president would obviously win.


“Both of them despise playing by the rules, so it’s who will cheat first,” Kasparov told me in an interview for POLITICO’s Off Message podcast. “But in any game of wits, I would bet on Putin, unfortunately.”

For the past 10 months, Kasparov has watched Trump’s interactions with the Russian president, and he thinks Trump is playing exactly into what the Kremlin wants while apparently refusing to understand Putin’s goals.

That’s a change from prior administrations. Kasparov argues that George W. Bush and Barack Obama got Putin wrong, and inadvertently helped the Russian president expand his power. But on some level, they also understood the strategic threat Putin posed—something he doesn’t think Trump grasps. “You can lose the war even if you have [an] overwhelming advantage—militarily, economically, technologically—if you don’t recognize you are at war,” Kasparov says.

Trump, Kasparov says, “operates in really a short-term environment. … [T]he way he communicates with the world definitely shows lack of any strategical calculations.”

Please, Kasparov says: Stop calling this chess.

“When I hear phrases like ‘Putin plays chess, Obama plays checkers,’ or moreover, ‘Trump plays chess,’ I feel I have my duty to defend the game that I have been playing for decades. The game of chess is game of strategy; of course, you have many opportunities to show your tactical skills, but foremost, it’s about strategy. And also, it’s a transparent game. It’s 100 percent transparency,” Kasparov says. “You know what I have; I know what you have. So, we don’t know the intentions of the opponent, but we know the resources our opponent can use to do us harm.”

In the 1980s, the half-Jewish, half-Armenian Kasparov won international celebrity after becoming, at 22, the youngest men’s world chess champion in history. Such prowess on the global stage made him a symbol of Soviet pride back home—the sport was an “important tool to demonstrate an intellectual superiority of the communist regime over decadent West,” Kasparov says—even as he personally came to detest the communist system. His love of chess fostered his awareness of politics: He began traveling internationally for chess matches at age 13, affording him the opportunity to “see the differences” between the USSR and capitalist countries. This political awakening made his status as a national hero all the more powerful, and he used that perch to voice support for the fight for reform and freedom in the Soviet Union throughout the late ’80s and early ’90s.

So concerned was Kasparov by Russia’s backslide into authoritarianism that, in 2008, he tried to run for president of Russia against Putin’s temporary presidential placeholder, Dmitri Medvedev, only to be barred from the ballot by the kind of technicality built in to block opposition leaders—the government’s stated rationale was that he hadn’t rented the right-size space to gather supporters—and ended up boycotting the election.

Now, from his home in New York, Kasparov watches Putin’s actions, frustrated by what he sees as the lack of chesslike geopolitical strategy from democratic forces. “We’ve yet to see political leaders who can think beyond their term in the office,” he says. “That’s what strategy means, because in democracy, you have continued [government]. A dictator doesn’t care what happens when he’s gone, so it’s all about survival.”

Click here to subscribe and listen to the full podcast to hear Kasparov’s take on why Putin likes having enemies instead of friends now, and whether he can beat the chess app on his phone.

Kasparov has never met Putin, but he was suspicious of him from Day One, writing an op-ed in the Wall Street Journal warning about him shortly after President Boris Yeltsin surprised the world by picking his prime minister as his successor on New Year’s Eve 1999. Just being a KGB officer was reason enough to worry, Kasparov says, but that was compounded by all of Putin’s talk of what a catastrophe the fall of the USSR was, and then restoring the old Soviet national anthem.

Just like now, Kasparov says, Putin was emboldened by the rest of the world not having much of a response when he seized businesses, attacked the free press and had political opponents killed.

“The leaders of the free world pretended, or believed, that Putin could be a good partner,” Kasparov says. “Yes, maybe he did something that they wouldn’t approve in Russia, who cares? Because he could be someone to work with on the international arena.”

Kasparov said Putin worked over George W. Bush KGB-style, reading up on being a born-again Christian and tailor-making a story for him about being secretly baptized and wearing a hidden cross. With Obama, he made a big show of having to work out a deal on Syria, Kasparov said, but “there was no common ground, because even if Putin pretended that he wanted to help in Syria, it was all about just using an opportunity, and he was very good in grabbing every opportunity. The moment Obama created a vacuum, Putin grabbed it.”

The takeaway lesson for the world from Bashar Assad’s survival, in Kasparov’s estimation: “This, for Putin, is a demonstration that if you stick with me, I will protect you, even if the United States, the most powerful nation on Earth, wants you out.”

Enter Trump. Kasparov says that unlike most people, he was able to watch the coverage in the American and Russian media side by side through the election and since. For the Russians, it was an obvious progression through the stages of people taking Trump seriously, starting out by saying Trump’s candidacy showed that all politics could be corrupt, then to saying that it spread chaos, then to saying he’d never win because the system was rigged even though he was a great guy.

“But then it was massive celebration, and you could read, sometimes between the lines, sometimes almost openly, preaching Trump as someone who would change everything in Russian relations,” Kasparov says. “I have no doubt that Putin’s dream was another big Crimea meeting, big Yalta to divide the world.”