Russia Experts Worry KGB Agent-Turned-Murderous Dictator Putin Will Play Trump

As President Donald Trump heads to Alaska to meet with the KGB agent-turned-dictator for whom he has long held a fawning admiration, Russia experts worry that the big loser will be Ukraine, the neighbour Vladimir Putin invaded three and a half years ago.

“There’re lots of ways this can go wrong,” said Fiona Hill, a Russia analyst on the National Security Council during Trump’s first term. “I’m kind of worried about the fact that it’s supposed to be a one-on-one.”

Trump is traveling to Joint Base Elmendorf-Richardson in Anchorage for the meeting with Putin, with the stated goal of ending the bloodshed caused by Russia’s invasion. It will be Trump’s first meeting with Putin, now widely considered a war criminal, since he returned to office in January. Putin would face arrest travelling to most countries and needed a waiver of US sanctions to set foot on American soil.

Trump’s summit, though, was hastily scheduled with little groundwork, apart from meetings conducted by his friend from his New York real estate days, Steve Witkoff, whose last trip generated confusion after Witkoff apparently misunderstood Putin’s demands.

“I think that the main thing to watch is whether Putin is able to use his KGB training to bring Trump back under his spell,” said John Bolton, Trump’s national security adviser at the time of his only previous summit with Putin in 2018. “And they can get back to being Vladimir and Donald, the good friends that Trump thought they were until they couldn’t get a ceasefire out of Putin for the first six months of this term.”

How much Trump actually pushes Putin to end his slaughter in Ukraine remains to be seen. In the days following the invasion in February 2022, Trump called Putin a “genius” and “savvy” for having done so. As former President Joe Biden pulled together a coalition to help Ukraine, Trump instead began blaming Biden and claiming that Putin never would have invaded had Trump remained in office.

For most of last year, Trump promised he would end the war on the day he returned to the White House or even before. Two hundred and seven days later, Russia’s assault continues, with missile and drone attacks on civilians only getting deadlier and more frequent.

Only in recent weeks has Trump acknowledged the brutality of Russia’s attacks. He did so again on Wednesday when asked if he thought he could persuade Putin to stop. Trump responded that he thought he had made that case to Putin several times now, only to see yet more bombardments that night.

“So I guess the answer to that is no, because I’ve had this conversation,” he told reporters during a visit to the Kennedy Center.

Ukrainian President Volodymyr Zelenskyy and leaders of America’s European allies, meanwhile, tried to head off potential disaster by preemptively arranging a call with Trump on Wednesday to warn him that Putin’s word has little value.

“It’s [the] most important thing that Europe convinces Donald Trump that one can’t trust Russia,” Polish Prime Minister Donald Tusk told reporters after the call with Trump.

Germany’s new chancellor, Friedrich Merz, said leaders “made it clear that Ukraine must be at the table as soon as follow-up meetings take place.”

“Trump has already given Putin the gift of a meeting with the president of the United States in the United States,” said Michael McFaul, a former U.S. ambassador to Russia and now a professor at Stanford University. “I hope Trump has a strategy for getting something in return. So far, I see little evidence that he does have a strategy. Eager to be proved wrong on Friday.”

For Trump, though, the fact that he is having a summit with an autocratic leader could well be more important than any particular result.

Trump was dazzled by the reception he received when he visited China’s Xi Jinping in Beijing in November 2017, gushing over the food, his trip to the Forbidden City, the military display. “My feeling towards you is incredibly warm,” he told Xi. “You’re a very special man.”

For years, Trump boasted that he was the first U.S. president to meet with North Korea’s dictator in 2018. He proudly displayed a photo in the West Wing of himself shaking hands with Kim Jong Un after Trump subsequently traveled to the DMZ during a trip to South Korea. After he lost reelection in 2020, Trump took the photo with him and hung it in a restaurant at his Trump Tower in Manhattan.

“He enjoys palling around with them. He thinks Xi Jinping is a friend,” Bolton said. “After the first meeting in Singapore with Kim Jong Un, Trump said they fell in love.”

Trump similarly sought out a one-on-one meeting with Putin during his first term, even though there was no agreement or even a framework to finalize — the customary prerequisites for a summit. At the end of that meeting in Helsinki, Trump infamously declared he believed Putin, a trained Soviet-era spy, over his own intelligence agencies about Russia’s work to help him win the 2016 election.

Trump’s claim that he would be able to end the war in Ukraine in a single day stemmed from his view that he “got along great” with both Zelenskyy and Putin — a questionable assertion, at best.

While Trump has been trying to curry favour with Putin since at least 2013, when he was hosting a beauty pageant in Moscow — “Will he become my new best friend?” Trump wrote on social media — there is no evidence Putin respects Trump.

Indeed, heading into the Alaska meeting, Putin openly insulted Trump and the United States generally by awarding an Order of Lenin medal to a CIA official whose son was killed in Ukraine while fighting for Russia. The 21-year-old suffered from mental health problems, and that medal has been obsolete since the dissolution of the Soviet Union.

Putin’s government also announced this week that the only way to end the war was for Ukraine to give it all the territory that Russia has been unable to take by force after 42 months of trying.

And Trump’s relationship with Zelenskyy began with his attempt to extort him into announcing an investigation into then-candidate Biden, withholding congressionally approved military aid as leverage. Trump was ultimately impeached for his actions, but remained in office because all but one Republican senator voted not to remove him.

Trump has ever since then disparaged Zelenskyy, at one point even calling the democratically elected leader a “dictator.”

Even if Trump’s personal views toward Putin and Zelenskyy did not complicate matters, Bolton said he wonders what purpose a meeting with Putin serves right now.

“The Russians understand force, and right now, Putin is being told he’s winning on the battlefield, and I think by at least some metric, he is,” he said. “The only way to get the Russians to negotiate seriously is to do more to show that their military position in Ukraine is weak, to show that if they don’t negotiate, Ukraine is going to win the war.”