Donald Trump and Vladimir Putin have a much-anticipated face-to-face meeting in Alaska on Friday, where the two leaders are set to discuss potential pathways to end the war with Ukraine.
If all goes well, Ukrainian President Volodymyr Zelenskyy could get the next invite.
Trump and the White House have described the meeting as an opening play to larger negotiations, casting it as a first step toward possible trilateral talks between the three leaders.
Trump’s history of cozying up to, and then lashing out against, the Russian president has given America's European allies reservations about Friday's meeting. European leaders told Trump this week that he must inform Putin that the territorial integrity of Ukraine — and Europe's security more broadly — must be respected.
The U.S. president entered office vowing to put an end to the yearslong war, though over time his outward assurances that he will be able to strike a ceasefire deal with his Russian counterpart have waned, as Putin has staunchly refused to cooperate in any meaningful peace talks.
Friday's meeting will put that question to the test. Trump and Putin will meet one-on-one at the Elmendorf-Richardson military base in Anchorage, Alaska, with only translators present. Following the smaller conference, American and Russian delegations will meet to continue the conversations. And the two men are then scheduled to hold a press conference.
Meanwhile, Zelenskyy and the rest of Europe will wait to see if — and how — Trump’s meeting with Putin might change the direction of the war.
With all eyes on Alaska, here are six questions going into the potentially pivotal get-together.
How long is the meeting? And what might that say about its success or failure?
A short meeting in Alaska may confirm what many Kremlin watchers believe: that peace remains a long way off. Trump on Monday told reporters he’d know if a deal could be reached “probably in the first two minutes.”
“I’m gonna go and see the parameters,” he said. “Now I may leave and say good luck and that’ll be the end. I may say this is not going to be settled.”
A long meeting, however, might mean the two presidents are getting somewhere.
“The time [of the meeting] will depend on how the discussion goes. There are, of course, time parameters, but I told you when the negotiations will begin … when they will end — this will depend, first of all, on the presidents,” Kremlin aide Yuri Ushakov said on Thursday.
Does Zelenskyy get a call?
Trump has outlined his order of operations for Friday’s meeting, telling reporters at a Kennedy Center event on Wednesday “I'm going to call President Zelenskyy,” and then ring up other European allies to debrief them on the talks. But that’s only if the meeting goes well. If it goes poorly, “I’m not calling anybody,” Trump told Fox News’ Brian Kilmeade on Thursday.
Whether Trump follows through on his promise to immediately get his Ukrainian counterpart on the line could also indicate whether or not Zelenskyy is being sidelined in the negotiations process.
Both Zelenskyy and his European allies have argued that no decision about Ukraine’s future should be made without Ukraine at the table. When, or if, Trump makes those calls in the hours after his one-on-one with Putin — and what world leaders discuss — will determine if Zelenskyy and the U.S.’s European partners feel like they’ve been pushed out of the critical talks.
Trump’s eventual conversation with Zelenskyy could also determine the possibility of a Putin-Trump-Zelenskyy trilateral, which Trump has said would be the ideal outcome of Friday’s meeting.
Is the Trump-Putin bromance back on?
The tone Trump takes in his conversations with — and about — Putin are likely to be an early tell of his interest in forcing Russia to get serious about a deal.
While he was laudatory of the Russian leader during the first few months of his term, Trump has soured on his former pal more recently. The U.S. president has taken a markedly harsher approach toward Putin in the past few weeks, expressing frustration in the Russian president's stalling tactics and threatening sanctions if the Kremlin fails to come to a ceasefire agreement.
On Wednesday, Trump once again assured reporters that there would be "severe consequences" if Putin isn't willing to strike a deal, though he declined to go into detail on what those repercussions would look like.
Speaking with reporters aboard Air Force One on the way to Anchorage Friday, Trump said Ukraine will be the ultimate decision-maker on any territory swaps.
“They'll be discussed, but I've got to let Ukraine make that decision,” Trump said. “I'm not here to negotiate for Ukraine. I'm here to get them at a table."
Any sign that Trump's stance toward Putin is softening could frustrate his European allies' and their hopes of coming down hard on Putin.
Will Trump bring up security guarantees for Ukraine?
Central to Ukraine's demands heading into any prospective peace talks with Russia: clinching security guarantees from the U.S. and other global powers.
Zelenskyy has long sought to secure commitments from Trump to provide deterrence against any future Russian advances under a potential future ceasefire agreement. Trump has for months dodged making any such assurances, declining to speak publicly about the prospect of U.S. support.
But ahead of Friday's bilateral, Trump indicated to European and Ukrainian leaders that he would be open to making that commitment — with some conditions. POLITICO previously reported that the president would only be willing to provide security guarantees outside of the NATO umbrella. And Trump has made clear that the U.S. would no longer directly supply Ukraine with weapons, though it would continue selling weapons to Europe that could be used by Kyiv.
Both Ukraine and its European allies would breathe a sigh of relief if Trump discusses the possibility of a security pledge on Friday, as it would indicate that the president is serious about backing Ukraine through any potential ceasefire.
Is a land swap on the table?
It’s clear that Putin wants Ukrainian land as part of a deal to end his war. Both Trump and special envoy Steve Witkoff are open to the possibility. Peace will require “land swapping,” the president said on Monday.
And a proposal the White House has weighed would see Ukraine give Donbas up to the Russians in exchange for a pause in their offensive down south.
Zelenskyy, however, is flatly rejecting the idea that Kyiv might part with its territory in negotiations to stop the fighting — especially without ironclad security guarantees.
“We will not leave Donbas. We cannot do this. Donbas for the Russians is a springboard for a future new offensive,” the Ukrainian president said in Kyiv on Tuesday.
If Trump comes out of the meeting with a land swap on the table — especially one involving more than just Donbas — he’s unlikely to find a willing partner in Zelenskyy. And a lack of sufficient security guarantees could sink the prospects of a deal altogether.
Will Trump and Putin make a deal that doesn’t relate to Ukraine?
It may well be that the most lasting element of Friday’s bilat could have little to do with Kyiv. Nuclear talks could prove a far more fruitful space for Trump and Putin to focus their energy. And with the New START treaty — the final agreement keeping in check the American and Russian nuclear stockpiles — set to expire next February, both sides see nuclear arms control as a priority.
Putin could of course dangle other prizes to defray Trump’s ire.
Ushakov, the Kremlin aide, said in a Thursday statement that Moscow expects to talk about enhancing cooperation “in the trade and economic spheres.”
“It is worth noting that this cooperation holds immense, yet regrettably underutilized, potential,” he said.
In Trump world, geopolitics can often take a backseat to commerce. Friday’s meeting could be yet another proving point.
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