Russian President Vladimir Putin and US President Donald Trump hold a bilateral meeting at the G20 Osaka Summit 2019. Photo / Getty Images
Donald Trump says that within two minutes of meeting Russian President Vladimir Putin in Alaska, he will know “exactly whether or not a deal can get done” to end the war in Ukraine.
For the Ukrainians and Europeans, there is more than just a whiff of Munich about this summit, with neither party receiving an invitation for the crunch talks.
In 1938, Adolf Hitler, Benito Mussolini, Edouard Daladier and Neville Chamberlain agreed to carve up Czechoslovakia without representation from the Czech government.
The concern is that this could happen once again with the United States President and his Maga acolytes busy discussing “land swaps” and criticising Ukrainian President Volodymyr Zelenskyy for arguing that his constitution bars him from doing so.
On the other end of the negotiation is Putin, an autocrat who believes Ukraine is a work of fiction and a mortal threat to his country.
The Telegraph has spoken to a host of former officials and diplomats who have first-hand experience dealing with both the Russian and American presidents.
Trump characterised his goals for the high-stakes meeting as an opportunity to stare into his Russian counterpart’s eyes to judge his plan to end the war in Ukraine.
“I’m going to see what he has in mind,” the US President told reporters.
“I may leave and say good luck, and that’ll be the end,” he added.
“Probably in the first two minutes I’ll know exactly whether or not a deal can get done.”
If he is prepared to walk away at the slightest demonstration that Putin isn’t ready to end the war – Zelenskyy says Russia is gearing up for more conflict – then what does Trump want?
It has long been thought that he is desperate for a Nobel Peace Prize and has a particular grudge against President Barack Obama for being decorated only eight months into his first term.
The Norwegian Nobel Committee cited Obama’s “extraordinary efforts to strengthen international diplomacy and co-operation between peoples”, which seemed to be more about Obama’s promise as an international leader than his actual accomplishments.
Trump is the self-styled “president of peace”.
“As president, he has brokered peace between Azerbaijan and Armenia, Cambodia and Thailand, Israel and Iran, Rwanda and the Democratic Republic of the Congo, India and Pakistan, Egypt and Ethiopia, Serbia and Kosovo, and with the Abraham Accords,” the White House said.
“Trump and certainly [JD] Vance, they don’t care about the future of Ukraine particularly,” Anthony Gardener, who served as Obama’s US Ambassador to the EU, said.
“I’m convinced Trump does want to position himself as the person who, quote, unquote, brought a sort of form of peace to get a Nobel Peace Prize,” Gardener added.
Ending the bloodshed in Ukraine could do that.
Others say he’s looking for yet another deal to sell as a demonstration of business acumen.
There are significant rare earth mineral deposits in eastern Ukraine. That territory is on the table, and Trump has already made a play for it by signing an agreement with Zelenskyy to be able to mine it.
“Trump wants to bag a win … period,” Gardener said.
In his office in the Kremlin, where Putin will be preparing for his meeting with Trump, sits a bust of Catherine the Great.
The significance of the monument should not be lost.
As Russia’s longest-serving female monarch, Catherine dragged the country into the 18th century and during her reign, doubled the size of its empire.
David Liddington, a former deputy prime minister, said Putin also compares himself to Peter the Great, “somebody who is going to restore Russia’s greatness and grow Russia’s territory, at least its effective empire”.
And Putin is likely to double down on his positions, in an attempt to at least cement his control over the Ukrainian territory already seized by his invasion forces.
He will leave little of the planning up to his aides, who are mostly believed to be yes men there for affirmation rather than assistance.
“President Putin is secretive, well-scripted and always eager to press an argument that reaffirms his positions rather than his willingness to settle. He reflects the attitudes of someone who’s familiar with power play, intelligence and security considerations, not the transactional, commercial kind of negotiation playbook,” Margaritis Schinas, a former European Commission vice-president, said.
According to Bobby McDonagh, a former Irish ambassador to the UK, Italy and EU, Putin is “utterly predictable”.
“He will relentlessly and ruthlessly pursue his very narrowly defined idea of Russian interests,” McDonagh added.
Those who have been in the room before say the Russian President will likely try to corner his American counterpart by demanding that the structure of their meeting plays out in a specific fashion.
“He prefers meetings structured in two parts: first, with delegations and interpreters that mainly serve as an audience to listen to his position on a particular subject, usually peppered with aggressive comments on those who think otherwise; then, a more closed – usually tete a tete – discussion of principals where he may show some margin of openness,” Schinas said.
It is in the latter section of the meeting in which Putin will try to hammer home any wriggle room he has made for himself.
“Putin will keep his eye on the strategic prize. He will look for opportunities to lessen the economic pressure on Russia and the Russian economy,” Liddington said.
The UK Foreign, Commonwealth and Development Office estimates that sanctions on Russia have deprived the Russian state of at least £333 billion ($755b) in war funds between February 2022 and June 2025.
Any easing would give Putin a significant win.
John Bolton, Trump’s former national security adviser, told the Telegraph that Putin will use his KGB skills to manipulate the US President.
“That’s one reason why Putin really did not want Zelenskyy or the Europeans there. He doesn’t want Trump to be distracted with all these other players,” Bolton said.
“Putin will try to get Trump back into feeling that they’re friends again. I think Trump has been disappointed that his friend, over the first six months of the Administration, has not helped him reach this deal.”
According to Bolton, Putin has “manipulated Trump on Ukraine really right from the beginning of the Administration, but back before the disaster with Zelenskyy in the Oval Office”.
The Russian President is “going to try and get Trump back on side”, Bolton said, adding: “He’s got to work fast”.
“The outcome will depend entirely on whether Trump resists Putin’s known and entirely unacceptable demands,” McDonagh added.
He was referring to a stripped-back Ukrainian Army, no prospect of them joining Nato, and the recognition of Russian sovereignty over the Ukrainian regions of Crimea, Donetsk, Luhansk, Zaporizhzhia and Kherson.
The US President is much happier to consult with advisers on his positions in the meeting, but those don’t bode well for Ukraine.
Tulsi Gabbard, his intelligence chief, is known to not care much for Kyiv. Vance and Pete Hegseth, the Defence Secretary, have vocalised the need for Ukraine to surrender territory.
“He likes to be surrounded by his team and advisers, allowing them space for contributions, but under no circumstances margin for decision,” Schinas said.
This means the US President is unlikely to listen to the European leaders, including Keir Starmer, who were to hold talks with him overnight.
There is one hope among the European and Ukrainian onlookers ahead of the summit.
Is Trump prepared to let himself be embarrassed at the hands of Putin?
Will he attempt to emulate Ronald Reagan, the former US president credited for the invention of “Make America Great Again”?
Sir Julian King, Britain’s last-ever European Commissioner, said: “You can get unexpected outcomes”.
“Reagan at Reykjavik blindsided his allies,” he said, referring to the 1986 summit between the US president and Mikhail Gorbachev which ushered in the end of the Cold War.
“But as they meet for the first time in years, with Putin’s maximalist negotiating and Trump’s unpredictability, anything could happen.
“The one potential saving grace, Trump won’t want to come out looking like a chump,” he concluded.