7 months of calls, trips and meetings that end in Alaska

Geneva, June 16, 2021. The location and date mark the last time the heads of state of Russia and the United States met in person, on the occasion of a meeting between Joe Biden and Vladimir Putin. Looking further back, to 2019, we arrive at the last meeting between the Russian president and Donald Trump. This Friday, the American and Russian presidents will meet again, at a summit in Alaska to discuss ending the war in Ukraine—the first time the leaders of the two countries have met since Russia invaded Ukraine in February 2022.

The in-person meeting with his Russian counterpart was one of Trump's goals upon returning to the White House, as part of his promise to end the war "within 24 hours." The deadline was "figurative" and an "exaggeration," he later explained , but efforts to achieve his goals were nonetheless accelerated. Only 23 days after his inauguration, he held his first phone conversation with Putin , thus reestablishing a connection that had been silent for precisely three years—we have to go back to February 12, 2022, to find the last phone call between the White House and the Kremlin, twelve days before the invasion.

Days after the first phone call, Washington and Moscow sat down for the first time, in a meeting between delegations led by Secretary of State Marco Rubio and Foreign Minister Sergey Lavrov, respectively, in Riyadh. The meeting in the Saudi capital was repeated the following month and resulted in the announcement of a 30-day truce in attacks on energy infrastructure, a ceasefire that was never fulfilled. Even so, the United States' entry into the fray opened the door for Ukraine and Russia to resume direct negotiations for the first time since May 2022.

A series of meetings in Turkey between May and July 2025 resulted in the release of thousands of Russian and Ukrainian prisoners of war. But the ceasefire Washington hoped for never came. During the same period, contacts continued: Trump and Putin held at least six phone calls , and White House special envoy Steve Witkoff traveled to Russia five times for in-person meetings with Putin. The latest visit, last Wednesday, resulted in a plan for the two presidents to finally meet in person. The Alaska summit represents yet another milestone: it will be Putin's first visit to the United States in a decade.

It took seven months of phone calls, trips, and meetings between diplomatic representatives to reach the highly anticipated summit. However, the long road to Alaska wasn't a straight line. Both sides had to adjust their expectations, strategies, and even the teams they presented to the summit with in an attempt to achieve the defined objectives. But even this evolution doesn't guarantee that Trump or Putin will emerge from the meeting with the desired results.

In February 2022, days after Russia invaded Ukraine and triggered a war between the two countries, a Russian and a Ukrainian delegation met in Belarus to try to reach a ceasefire. These meetings were repeated in Turkey until the summer of that year. Moscow's demands included the demilitarization of Ukraine—including an end to its aspirations for NATO membership—the annexation of the occupied territories of Donbass, and the resignation of Volodymyr Zelensky as president. Ukraine, whose security guarantees and territorial sovereignty remain the most important negotiating grounds, rejected the proposal.

More than three years later, Vladimir Putin's position appears inflexible. The Russian president continues to insist on the annexation of all of Donbass, which would include territories currently under Ukrainian control, and on the departure of Zelensky, who has now exceeded his presidential term and remains in office due to martial law, which prevents elections from being held. The Russian leader's inflexibility is justified by the perception that he is winning the war.

" Putin believes he's winning and therefore has no reason to bow down ," a US source familiar with US intelligence information on Putin told CNN . However, the intelligence services also identified signs that the Kremlin's position may be more flexible than it lets on, and that Russia would be willing to accept only control of the occupied territories in exchange for the United States not imposing sanctions or secondary tariffs that would further harm the current state of the Russian economy.

On the other hand, Donald Trump's stance has been much more flexible . He began by pressuring Volodymyr Zelensky to accept a deal, saying that Kyiv had no "cards" to dictate peace terms during their controversial Oval Office meeting in late February. After that, he approached the Ukrainian leader and escalated his criticism of Putin. When it comes to concrete demands, Washington continues to advocate for a 30-day ceasefire , as it did in negotiations in Riyadh and Turkey throughout this year.

This Thursday, in anticipation of the meeting and after being pressured by European leaders to do so, Trump emphasized that the priority for Alaska is an "immediate peace agreement," that is, a truce in the fighting. Only later, in a three-way meeting with Ukraine, could the details of a long-term agreement be discussed. However, the US president continues to not rule out the possibility that an agreement would require territorial concessions from Kyiv—" a give and take of borders, land ," he elaborated.

In late March, after another call between Putin and Trump, Volodymyr Zelensky accused his Russian counterpart of "trying to buy time" and delaying a peace agreement so he could continue the war. On the eve of a face-to-face meeting, Putin's strategy, like his demands, appears to have remained unchanged.

Just as he previously accepted a ceasefire that was never fulfilled but which eased Donald Trump's frustration, Ilya Budraitskis, a Russian political scientist at the University of California, Berkeley, believes he could make certain concessions in Alaska that wouldn't impede advances in Donbass. "It's possible that Putin will take symbolic steps , for example, temporarily limiting bombings of Ukraine, because, overall, this air war does little to help Russian troops advance," he argued to Al Jazeera .

Among Vladimir Putin's supporters, the strategy is interpreted differently. Yury Podolyak, a prominent pro-Kremlin blogger, called it "a masterclass in diplomacy" and a "substantial diplomatic victory." The praise stems from Putin's ability to arrange a meeting in Alaska without the intervention of Zelensky or other European leaders, which is seen as a way to defend Russian interests while simultaneously enhancing the bilateral relationship between Washington and Moscow.

This is because Alaska is a former Russian territory, still claimed as such by Russian ultranationalists. At the same time, it's a way to highlight the historical connection between the two countries as major world powers —which could please Trump, who is notoriously susceptible to flattery from international leaders. It could also serve to repeat a formula already used in the meetings in Riyadh, where the Russian delegation steered the negotiations toward improving bilateral relations between the two countries, rather than toward ending the conflict in Ukraine.

However, the US president's strategy appears to have evolved since January—and since 2019. Initially, Trump's diplomacy involved establishing a good personal relationship with his counterparts so that negotiations could be conducted from a friendly place. This explains why Trump's top priority on his to-do list to end the war was calling Putin directly.

Seven months later, this strategy hasn't worked, and Trump is playing new cards. In public, the president lowered expectations and announced that it was a "meeting to take [Putin's] pulse," while spokeswoman Karoline Leavitt described it as "a listening exercise ." However, privately, Trump reportedly realized that negotiating with Vladimir Putin cannot be done from a place of kindness, but from a place of strength.

"His approach in early January was naive. Now, Europeans say he finally realizes Putin is a murderous leader," a US official told CNN . Quoting US and European officials, the channel describes how advisers and international leaders spent the first months of the Trump administration trying to explain to the president that the Putin he had met with during the first administration—for example, during the only bilateral meeting in Helsinki in 2018 , when Trump took Putin's word over his own intelligence services—was not the same one he was facing now. Americans attribute the change largely to self-imposed isolation during the pandemic, which narrowed their inner circle and trusted confidants.

"Putin is much more ideological today than he was in previous years. He's not a transactional leader, as many in the West assumed in the past, but he's more motivated by imperial ideas. Someone with that mindset is harder to negotiate with," Michael McFaul, former US ambassador to Russia, told the American channel.

Trump's new approach to his interlocutor is reflected in a slightly more aggressive strategy. This was evident in the threat of sanctions and the imposition of secondary tariffs against India for purchasing Russian oil, which reportedly led Vladimir Putin to agree to the in-person meeting. This Wednesday, the threats were repeated : if Putin doesn't agree to end the war, there will be " very severe consequences ."

On February 18, 2025, the Trump administration sat down for the first time in front of a Kremlin team. The US President's three most trusted men traveled from Washington to Riyadh: Secretary of State Marco Rubio, then-National Security Advisor Michael Waltz, and Special Envoy Steve Witkoff, a personal friend of Trump's who rose from Middle East envoy to Special Envoy for Peacekeeping.

With the exception of Waltz's departure, who was removed from his post and handed it over to Rubio, the US delegation to negotiate with Moscow has remained virtually unchanged: Witkoff traveled to Moscow for multiple meetings with Putin, and Rubio, as chief diplomat, has led the US team. Other members will join to complete the five-person delegation, but it will remain a small team, made up of trusted figures in the President's inner circle, a reflection of his personalized approach to diplomacy.

The teams that have represented the Kremlin in negotiations over the past three years reveal more about how Russia practices its diplomacy. In 2022, in the first negotiations with Ukraine, the Russian delegation consisted of Vladimir Medinsky , a former Kremlin adviser and minister, and members of the Ministries of Foreign Affairs and Defense. Unofficially, the Kremlin also enlisted millionaire Roman Abramovich to negotiate on its behalf, who, behind the scenes , served as a bridge between the irreconcilable positions between Moscow and Kyiv.

This year, back in Turkey, Medinsky once again led the Russian delegation , complete with the head of the military intelligence service, the deputy defense minister, and the deputy foreign minister. The delegation did not include any of Russia's diplomatic heavyweights, which contrasted with the team Kyiv sent, which included Defense Minister Rustem Umerov, Zelensky's chief of staff and right-hand man, Andriy Yermak, the foreign minister, and the head of the armed forces and security services.

However, when it comes to negotiating directly with the United States, Moscow spares no diplomatic effort. Behind-the-scenes figures close to Ukraine and minor figures have been replaced by high-level diplomats and influential figures with ties to the United States. This shift in stance was evident in the negotiations in Riyadh, when Moscow sent Minister Sergey Lavrov , advisor and former ambassador to Washington Yuri Usahkov , and Special Representative for Investment and Economic Cooperation and a former banker who studied and worked in the United States, Kirill Dmitriev .

These three prominent figures are part of the delegation that will make the nine-hour journey from Moscow to Alaska, along with Defense Minister Andrei Belousov and Finance Minister Anton Siluanov. The inclusion of financial experts alongside more traditional diplomats points to Vladimir Putin's goal of moving the negotiations toward bilateral relations while keeping the possibility of new economic sanctions at bay, analyzes Pjotr Sauer, Russia reporter for The Guardian .

75% . This is the chance of success Donald Trump predicts for the Alaska summit. Despite all the adjustments that appear to have been made since January—and even more so since the meetings with Ukraine in 2022 or between the two leaders in 2019—the US President admitted this Thursday that "there is a 25% chance that the meeting will not be successful."

A failed meeting for the President will be one that doesn't end with a truce and tentative plans for a future meeting with Volodymyr Zelensky. Optimism extends across the Atlantic after Wednesday's virtual meeting, in which European leaders, apprehensive about Putin putting pressure on Trump, persuaded the US leader to defend Kyiv's interests.

Now, the Kremlin appears much less inclined to make definitive decisions in Alaska. The Russian presidency announced this Thursday that there are no plans to sign documents during the summit . Furthermore, it would be "a big mistake" to try to predict the outcome of the meeting, it stated.

Despite Western optimism and Moscow's warnings not to look too far ahead, analysts aren't particularly confident that the meeting, even after all the adjustments, will result in concrete changes on the battlefield. "There was a realistic adjustment, and expectations were lowered," former US ambassador to Ukraine John Herbst told CNN . In this new environment, with new demands, strategies, and teams, the most likely scenario seems to be the implementation of symbolic gestures that both Putin and Trump can claim as a victory.

Berkeley's Ilya Budraitskis argues that Putin could demand "the restoration of his standing in the world" with an invitation to American soil and a face-to-face meeting with the president after several years. Furthermore, if Trump accepts any territorial concessions, he could prove the success of the strategy of "stubbornly repeating maximalist positions until everyone gets so tired of it that they are forced to accept them."

For Donald Trump, the meeting solidifies his vision as a president of peace —which contributes to his bid for the Nobel Prize —and as a respected international leader who can sit Putin down and force him to listen, he told Al Jazeera. The president's words this Thursday point in the same direction, stating that, even in the worst-case scenario, the meeting itself is already a victory. "If the meeting is not successful, I will return to the country, and we will have made America great again in six months," he concluded.