Trump’s Tumultuous Relationship with Putin: From Election Meddling to Alaskan Summit Amidst Ukraine Crisis

In their seventh face-to-face meeting, President Donald Trump and Russian President Vladimir Putin convene in Alaska, marking Trump’s first encounter with Putin since resuming office. Despite optimistic anticipation from Trump, the prospects of the summit remain uncertain, with a history of secretive interactions and controversial outcomes between the two leaders.

During their 2019 meeting in Japan, Trump described his relationship with Putin as positive, stating, “We have had a very good relationship…A lot of very positive things are going to come out of the relationship.” However, six years later, tensions between Russia and the United States persist, particularly regarding Moscow’s ongoing aggression toward Ukraine.

Trump, once hopeful that his rapport with Putin could facilitate an end to the war, now expresses disillusionment towards his former ally, accusing Putin of spreading “bullshit” over the telephone. This dramatic shift in tone signals a challenging backdrop for Friday’s encounter.

Trump expressed confidence that progress will be made during the summit, stating, “I believe now he’s convinced that he’s going to make a deal,” and adding, “I think he’s going to [make a deal]. And we’re going to find out – I’m going to know very quickly.”

The White House has characterized the meeting as a “listening exercise,” while Moscow insists a wide range of topics related to normalizing US-Russia relations will be discussed. The meeting at a U.S. airbase north of Anchorage, like Trump’s previous meetings with Putin, is shrouded in uncertainty regarding the specifics of their discussions and any agreements that may result.

At the heart of this complex relationship are two enigmatic leaders whose bond has fluctuated over the years. Their interactions have been characterized by praise, acrimony, and secrecy, leaving even some of Trump’s closest allies puzzled by his apparent alignment with Kremlin talking points.

In the eight years since their initial meeting on the sidelines of a Group of 20 summit in Germany, the relationship between Trump and Putin has navigated both cooperation and conflict. Trump has adopted Putin’s views on numerous occasions but has also canceled meetings out of anger and expressed concerns about Putin’s deteriorating behavior to other leaders.

“There’s a realistic adjustment and lowering of expectations,” said John Herbst, former U.S. ambassador to Ukraine and senior director of the Atlantic Council’s Eurasia Center. “Even Trump is pointing out, correctly, that maybe you can’t trust Putin.”

The shadow of the 2016 election, during which U.S. intelligence agencies found evidence of Russian interference on Trump’s behalf, continues to cast a long shadow over the leaders’ relationship. This history has colored Trump’s perspective on Russia and Putin for years, leading him to voice solidarity with Putin against what he refers to as the “Russia hoax.”

In recent months, Trump has threatened criminal prosecution against officials from the Obama administration, including former President Barack Obama himself, regarding matters related to the investigation into Russian election interference. Trump acknowledged that this investigation posed a strain on the relationship and hindered his ability to engage with Russia as he believed was necessary.

The election meddling allegations have overshadowed each of Trump’s previous meetings with Putin, including their inaugural session at the Hamburg G20 in 2017. That meeting lasted over two hours, with only Trump’s Secretary of State Rex Tillerson present. Afterward, Trump requested his interpreter’s notes to ensure that the contents of the discussion remained confidential.

At a leaders’ dinner during the same summit, Trump sought out Putin for an hour-long conversation without any other American officials present, save for Putin’s interpreter. The two men met again several times after this encounter, with Trump consistently expressing trust in Putin’s denial of election interference and indicating his belief that Putin was truthful.

When Putin was reelected the following year, Trump congratulated him on his victory despite advisors’ warnings against doing so due to concerns about the fairness of the contest. Putin has managed to maintain his position throughout five American presidencies, although the days of friendly interactions with leaders such as Bill Clinton and George W. Bush are long gone.

In recent years, Putin has faced increasing isolation on the global stage, punished for his actions in Ukraine and Crimea, the downing of a Polish plane, a nerve agent attack in the United Kingdom, and numerous other atrocities. An attempt at resetting relations with Obama, complete with a large red prop button, ultimately failed, leading to Russia’s expulsion from the Group of Eight nations.

Before being elected in 2016, Trump claimed to have been “stablemates” with Putin prior to an appearance on “60 Minutes,” though no evidence of the encounter ever materialized. After taking office, Putin sought to reestablish his influence on the global stage, hosting a marquee summit in Helsinki. This meeting only intensified a cloud of suspicion that still lingers today regarding Trump’s ability to challenge Putin effectively.

The Helsinki meeting, during which Trump met with Putin privately without advisors, fueled widespread criticism and concerns about Trump’s unwillingness to trust his own intelligence community’s findings on Russian election interference. Trump faced a torrent of bipartisan backlash – as well as global condemnation – for appearing to defer to Putin’s version of events over the evidence presented by U.S. intelligence agencies.

After returning to the White House, Trump admitted that he needed to clarify his remarks from the Helsinki summit. However, seven years later, following a series of conciliatory statements towards Putin and consistent promotion of their deep relationship, Trump now expresses skepticism about reaching a deal over Ukraine. This shift in attitude only occurred in May, when Trump suggested he would travel to Turkey to preside over a meeting between Putin and Ukrainian President Volodymyr Zelensky.

When this meeting never materialized, and Russia intensified its bombing campaign on Ukraine, Trump’s stance towards Putin hardened, and his expectations for resolving the conflict diminished. “I’m not happy with Putin,” Trump said last month in one of his sharpest remarks yet about the Russian leader. “We get a lot of bullshit thrown at us by Putin, if you want to know the truth. He’s very nice, all the time, but it turns out to be meaningless.”