Donald Trump's upcoming summit with Vladimir Putin in Alaska on Friday is anticipated to be a pivotal moment that could influence both the ongoing conflict in Ukraine and the unique dynamics of Trump's relationship with his Russian counterpart. Throughout his political career, Trump has consistently highlighted his rapport with Putin, even going so far as to describe him as “pretty smart” for his actions in Ukraine. However, recent months have seen Trump expressing growing frustration with Putin, hinting at potential sanctions against Russia.
As the summit approaches, Trump has delivered mixed messages regarding his expectations. He characterized the meeting as “really a feel-out meeting” aimed at assessing Putin’s willingness to negotiate a ceasefire, while also warning of “very severe consequences” if the Russian leader fails to agree to end the conflict. For Putin, this meeting represents an opportunity to mend ties with the U.S. and alleviate the Western isolation Russia has faced since its invasion of Ukraine over three years ago.
The White House has downplayed any implications that Trump's agreement to meet with Putin signals a victory for the Russian leader; however, critics argue that the summit could provide Putin with a platform to influence Trump at the expense of Ukraine, whose leader has been notably excluded from the discussions. Ian Kelly, a retired foreign service officer and former U.S. ambassador to Georgia, criticized the summit, stating, “I think this is a colossal mistake. You don’t need to invite Putin onto U.S. soil to hear what we already know he wants.”
In contrast, Republican Senator Lindsey Graham of South Carolina, a long-time advocate for a tough stance on Russia and a close ally of Trump, expressed optimism regarding the summit. “I have every confidence in the world that the President is going to go to meet Putin from a position of strength, that he’s going to look out for Europe and Ukrainian needs to end this war honorably,” Graham remarked on social media.
The relationship between Trump and Putin has been marked by significant ups and downs, beginning during Trump's 2016 campaign. At that time, Trump publicly questioned the findings of U.S. intelligence agencies, which indicated that Russian hackers had interfered in the election to benefit his candidacy. In a controversial statement, he even urged Russian hackers to find deleted emails belonging to his opponent, Hillary Clinton, saying, “Russia, if you’re listening, I hope you’re able to find the 30,000 emails that are missing.”
Throughout his first term, Trump faced scrutiny over his connections to Russia, which led to investigations by the Justice Department and Congress. These inquiries ultimately resulted in the appointment of special counsel Robert Mueller, who secured multiple convictions against Trump associates but did not establish a criminal conspiracy between the Trump campaign and Moscow. Trump later characterized the investigation as a shared ordeal, stating, “Putin went through a hell of a lot with me,” referring to it as a “phony witch hunt.”
During his first term, Trump met with Putin six times, including a notable summit in Helsinki in 2018, where he faced backlash for appearing to side with Putin regarding Russian interference in the 2016 election. Trump stated, “I have great confidence in my intelligence people, but I will tell you that President Putin was extremely strong and powerful in his denial today.” This remark led to significant criticism, prompting Trump to later attempt to clarify his stance, suggesting that other countries could have also interfered.
Putin has expressed that he viewed the Helsinki summit as the beginning of a potential thaw in U.S.-Russia relations, indicating that he had hoped Trump would win the 2016 election due to his vision for normalizing ties between the two nations. "Isn’t it natural to feel sympathy to a person who wanted to develop relations with our country?” Putin stated.
Following his presidency, Trump maintained a friendly view of Putin, even after the latter’s invasion of Ukraine in 2022. Trump remarked on the situation, saying, “I mean, he’s taking over a country for $2 worth of sanctions. I’d say that’s pretty smart.” He suggested that if he had been in office, the invasion would not have occurred, a sentiment that Putin echoed while supporting Trump’s unfounded claims of election fraud.
As the conflict has continued, Trump has shifted his rhetoric. While he previously claimed he could resolve the war in Ukraine in just 24 hours, he later described such statements as sarcastic. In recent months, Putin has expressed a desire for a summit, pivoting discussions towards potential U.S.-Russia economic collaborations. “We’d better meet and have a calm conversation on all issues of interest to both the United States and Russia based on today’s realities,” Putin stated in January.
Despite initial trust in Putin’s intentions for a ceasefire, Trump’s tone has changed as the conflict escalated. He has publicly urged Putin to halt military actions, expressing frustration with the Russian leader. Recently, Trump indicated that the upcoming summit is less about resolving the conflict than it is about assessing Putin’s position, stating, “I think it’ll be good. But it might be bad.”
