Both President Donald Trump and Russian President Vladimir Putin have spent the run-up to Friday's high-stakes meeting in Alaska staking out their public positions -- and signaling the strategies they may employ behind closed doors.
ABC News spoke to current and former officials as well as outside policy experts to break down both Trump and Putin's approach and the potential risks and rewards for each.
MORE: Trump-Putin summit live updates: Trump says he thinks Putin and Zelenskyy 'will make peace'
President Donald Trump in Washington, Aug. 14, 2025, Ukrainian President Volodymyr Zelenskyy in Berlin, Aug. 13, 2025 and Russia's President Vladimir Putin in Moscow, Aug. 12, 2025.
EPA/Shutterstock/AFP via Getty Images
A 75% chance of success?
Ahead of the summit, the White House initially tried to downplay expectations, first calling it a "listening session" for Trump to hear Putin's position on bringing the war in Ukraine to a close.
Through the week, Trump stopped short of making any promises, but he slowly began to build expectations, describing the summit with Putin as a steppingstone that -- if successful -- would set up another meeting that would include Ukrainian President Volodymyr Zelenskyy.
"This meeting sets up the second meeting, but there is a 25% chance that this meeting will not be a successful meeting," Trump said in a Fox News Radio interview on Thursday.
But Trump suggested if the summit with Putin were productive, it could set off a near-immediate whirlwind of diplomacy, with subsequent engagements happening very soon after the initial meeting and potentially at the same venue.
"All I want to do is set the table for the next meeting, which should happen shortly. I'd like to see it happen very quickly -- very shortly after this meeting," the president said during an Oval Office event at the White House on Thursday. "I'd like to see it actually happen maybe in Alaska, where we just stay because it's so much easier."
Officials familiar with the president's approach say his comments reflect his willingness to capitalize on opportunities as they may present themselves. They also acknowledged that even though intensive planning for the summit has been underway more than a week, the president could quickly pivot based on his impression of the meeting.
Trump previewed the potential for on-the-fly changes to the summit's programming schedule when he contradicted White House press secretary Karoline Leavitt's statement earlier on Thursday that the plan was to hold a joint news conference at the summit featuring both Trump and Putin.
"I'm going to have a press conference. I don't know if it's going to be a joint. We haven't even discussed it," Trump said, indicating the format would depend on how the meeting went.
Officials say Trump has been working closely with his Secretary of State and interim national security adviser Marco Rubio and Special Envoy Steve Witkoff ahead of the meeting, and that both men are expected to accompany the president to Alaska.
MORE: Putin says Trump making 'energetic' efforts to end war as summit nears
Britain's Prime Minister Keir Starmer welcomes Ukraine's President Volodymyr Zelenskyy to Downing Street in London, Aug. 14, 2025.
Kirsty Wigglesworth/AP
An "all-Trump" peace process
European leaders emerged from a virtual meeting with Trump on Wednesday with tones of relief that the U.S. would be involved in a security mechanism for Ukraine as a part of a settlement of the war – though Trump did not acknowledge such a vow publicly.
Zelenskyy and other European heads of state, who have said Russia's aggression in Ukraine is part of larger Russian ambitions, took part in hurried meetings this week to present consensus priorities to Trump.
From those meetings, the Europeans said a ceasefire should happen first in any Ukraine peace process.
Fred Fleitz, co-chair of the Center for American Security at the America First Policy Institute and a former chief of staff of the National Security Council during Trump's first term, said Trump's participation virtually in the Wednesday meeting will bring the president "a lot of credibility when he speaks to Putin," but ultimately, the peace process is "all Trump."
Trump's "job is to bridge" the parties in the conflict, Fleitz told ABC News, and test whether Putin is sincere about wanting an end to the war. Fleitz said he thinks Trump will have a "very critical eye" toward Putin and be "very quick to implement sanctions" if he judges Putin to be playing him.
President Donald Trump speaks after signing a presidential proclamation honoring the 90th anniversary of the Social Security Act in the Oval Office of the White House in Washington, August 14, 2025.
Will Oliver/EPA/Shutterstock
Trump has been open in saying Putin might be "tapping him along," a turnabout Fleitz says the "world understands."
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Fleitz and other experts who spoke with ABC News said a ceasefire is the most crucial outcome in this stage of the diplomatic process.
"If we're looking at some kind of a success or not" from Friday's meeting, "it has to be [in the] first instance a ceasefire," Bill Taylor, a former U.S. ambassador to Ukraine from 2006 to 2009 and a top diplomat there under Trump, told ABC News.
If no deliverable emerges from the summit, "then Trump hasn't won," Taylor said. "Trump hasn't gone into those negotiations and succeeded. He will have been defeated, or at least stalled again, and this will be recognized."
George Beeby, director of the Quincy Institute's Grand Strategy Program and a former director of the CIA's Russia analysis, said a ceasefire "that isn't well negotiated" is "actually much more risky" than working out particulars, including over issues like NATO, first.
The key deliverable Friday, in Beeby's view, is "a framework agreement that addresses these core issues and lays out a road map for further negotiations." Broader European security, instead of a temporary pause to the fighting, is the key issue at the table, he said.
Russia would view military forces from NATO countries as a part of a security guarantee for Ukraine as a red line, he said. Instead, Putin will seek a "rock-solid guarantee" that Ukraine wouldn't join NATO in the future -- something Beeby called Putin's "number one issue."
MORE: Trump-Putin summit in Alaska holds a 'historical significance,' experts say
Ian Brzezinski, a senior fellow and the Atlantic Council and a former deputy assistant secretary of defense for Europe and NATO policy, said a security guarantee would be essential for Ukraine -- and for the broader west, including the U.S to halt Putin's "revanchism" -- a policy of seeking to retaliate, especially to recover lost territory.
Putin "may try to push" a pledge that Ukraine won't join NATO to "never," but that "can really only ever apply to Trump," Brzezinski said. Any NATO member can veto a country's bid to join the alliance.
Trump has shown sympathy for the Russian position on NATO, blaming Zelenskyy for the war in Ukraine as recently as this week, apparently for his country's past NATO ambitions.
According to Fleitz, NATO may or may not come up in the meeting at all.
"It's a big issue for Putin, but there's no sense" in discussing it because accession to NATO has become exceedingly unlikely, Fleitz said. He said Trump's decision to prioritize American-made weapons, purchased by European nations for Ukraine, showed his commitment to the country's security.
MORE: Ukraine, left out in Trump-Putin summit, fears setbacks on key peace issues
Russian President Vladimir Putin holds a meeting with members of Russia's top leadership at the Kremlin in Moscow, Russia, August 14, 2025.
Vyacheslav Prokofyev/Pool via Reuters
'Putin's gonna try and play Trump'
Former officials and experts on the ongoing conflict have warned that Trump should keep his focus during Friday's summit on a potential ceasefire deal between Russia and Ukraine and note that Ukraine's leaders should have final say on territorial concessions -- and they cautioned Trump to remember he is dealing with a shrewd negotiator in Putin.
"President Trump needs to stick to his discussion points and not get carried away by the moment. Putin will be pushing for an agreement favorable to Russia, and Trump might be tempted to agree as a way to end the war, as he has promised," said Mark Cancian, a senior adviser on defense and security issues at the Center for Strategic and International Studies.
"It's very concerning that Ukraine is not part of the discussions. Putin does not regard Ukraine as a real country, and its exclusion seems to accept that position. Any follow-on discussions should include both Ukraine and the Europeans," he said.
Other experts suggest that Trump's video conference with European leaders boosted Ukraine's status ahead of Friday's summit and was strategic in helping to reassure allies that the US still backs Zelenskyy's position.
Meetings between European allies and Vice President JD Vance, for example, "was a sign that they want to make sure that they were not going to be blasted for cozying up to Putin in Alaska."
"Zelensky is not coming, but they want to make sure that they don't look like they are fatuous and being played by the Kremlin," said John Herbst, in an interview with ABC News. Herbst is a career diplomat and the former U.S. ambassador to Ukraine, having served in Ukraine from 2003-2006.
"Putin has no interest in making peace. He starts to talk about negotiations when he's afraid that there may be some new pain for Russia," Herbst said of the Russian leader.
"Putin's gonna try and play Trump, and he may have success. He's had some success in the past, but Trump's guard is up and again. That's why we saw his statement today. That's why we've seen some backtracking for the last three days," Herbst added, noting that Trump said this week that Russia will suffer "severe consequences" should Putin not make efforts to stop the war.
"I think Putin's hope is to really use this event to ensure that there'll be no sanctions in the future, that maybe US arms Ukraine are not going to be flowing. I think that's not going to be the case," Herbst said.
While former officials and experts on the war are worried about Zelenskyy's absence in this initial meeting given what Trump may agree to behind closed doors, Herbst remains optimistic.
"I think worry is always warranted in this case, because the situation is so difficult. But I think it would be a disaster for the United States if we sold out Ukraine," Herbst said. "I thought that could happen, but everything since has pointed in a healthier direction."