<div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>The last time US President Donald Trump shared a room with Russian counterpart Vladimir Putin, their relationship, perhaps the most scrutinised association of any two people in the entire world, was enjoying an upswing.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>"We have had a very, very good relationship. And we look forward to spending some pretty good time together," Trump said as their 2019 talks were getting underway in Japan. </span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>"A lot of very positive things going to come out of the relationship."</span></div></div><div><div id="adspot-mobile-medium"></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><strong><span>READ MORE: </span></strong><a href="https://www.9news.com.au/world/israel-gaza-update-mike-huckabee-details-us-reaction-australia-palestine-recognition/d1b0f06f-4242-41d3-89a9-94c04547739c" rel="" target="_blank" title="Disappointment and some disgust': US reaction to Australia's Palestine recognition plan"><strong><span>Disappointment and some disgust': US reaction to Australia's Palestine recognition plan</span></strong></a><strong></strong></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>Six years later, not much positive has happened when it comes to Russia and the US. </span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>Putin invaded Ukraine a year after Trump left office. And in the months since he's returned to the White House, Moscow has shown zero indication it will let up. Trump, once hopeful he might leverage his relationship with Putin into an end to the war, has grown disillusioned with his onetime friend, whom he now accuses of peddling "bullshit" over the telephone.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>That makes for an altogether darker backdrop to Friday's encounter between Trump and Putin in Alaska, their seventh face-to-face meeting and the first of Trump's new presidency.</span></div></div><div><div class="OUTBRAIN" data-reactroot="" data-src="//www.9news.com.au/world/how-donald-trump-and-vladimir-putin-relationship-evolved-since-first-meeting/828750e8-51ad-49a2-9236-6786230f1267" data-widget-id="AR_5"></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>"I believe now he's convinced that he's going to make a deal," Trump told Fox Radio on Thursday. "I think he's going to. And we're going to find out – I'm going to know very quickly."</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>Like all of Trump's previous meetings with Putin, the sit-down at a US air base north of Anchorage comes with a degree of uncertainty about what will be said, which outcomes will be agreed to and how it will be spun afterward. </span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><strong><span>READ MORE:</span></strong><span> </span><a href="https://www.9news.com.au/finance/ampol-eg-group/6450c950-318e-4654-8307-bf5d9c5c16a1"><strong><span>Servo giant confirms massive $1.1 billion takeover</span></strong></a></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>Already, the White House has lowered expectations for what it describes as a "listening exercise," even as Trump struck a more optimistic tone on Thursday for progress at the summit. </span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>Moscow, meanwhile, insists a whole litany of topics meant to normalise US-Russia ties are up for discussion.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>At the centre of it all will be two men with a decidedly tangled relationship — long scrutinised, often secretive and never quite fully understood, even by some of Trump's closest allies, who scratch their heads every time he seems to parrot a Kremlin talking point.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>In the eight years since the leaders first sat down together on the sidelines of a Group of 20 summit in Germany, the ties between the men have zigged and zagged. Trump has heaped praise on Putin and adopted his views, but he's also abruptly cancelled meetings in anger and told other leaders he thinks Putin has changed for the worse, advisers have said.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>"There's a realistic adjustment and lowering of expectations," said John Herbst, a former US ambassador to Ukraine and senior director of the Atlantic Council's Eurasia Centre. </span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><strong><span>READ MORE:</span></strong><span> </span><a href="https://www.9news.com.au/national/tarneit-fatheroftwo-critically-injured-in-melbourne-road-rage-incident/eed68dce-d5a4-4046-b4b1-71ffd5229eec" target="_blank"><strong><span>Father-of-two fighting for life after suspected road rage attack in Melbourne</span></strong></a></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>"Even Trump is pointing out, correctly, that maybe you can't trust Putin."</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>If there has been one constant, it is the shadow of the 2016 election, in which US intelligence agencies found Russia sought to interfere on Trump's behalf.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>Those findings - and the attempts from Congress and other officials to hold individuals accountable - have coloured Trump's view of Russia and Putin for years. </span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>He has voiced a certain kinship with the Russian leader for having to endure what Trump calls the "Russia hoax." Just this year, he threatened criminal prosecution against officials in the Obama administration - including former US president Barack Obama himself - for issues related to the probe.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>"It was a strain on the relationship," Trump said on Wednesday of the investigations into Russian election interference. He added: "It made it very dangerous for our country, because I was unable to really deal with Russia the way we should have been."</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>Indeed, the election meddling was a shadow over each of Trump's previous meetings with Putin, including their inaugural session at the Hamburg G20 in 2017. Those talks lasted more than two hours, with only Trump's secretary of state Rex Tillerson in the room.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>Afterward, Trump asked his interpreter for his notes to ensure the contents of the discussion weren't revealed. And at a leaders' dinner at the same summit, Trump sought out Putin for another hour-long talk — this time, without any other American officials nearby and only Putin's interpreter to translate.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>The two men would meet again several times after that, including at an Asian leaders' summit in Da Nang, Vietnam. Trump said afterward that Putin again denied interfering in the US election, and indicated he believed him.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>"I really believe that when he tells me that, he means it," Trump said.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>When Putin was reelected the next year, Trump congratulated him on his victory, despite a warning in all-capital letters from his national security team to "DO NOT CONGRATULATE" given questions about the fairness of the heavily managed contest.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><h3><span>Putin's isolation on the world stage</span></h3></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>Putin, 72, has stood the test of time through five American presidencies.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>Long gone are the days of strolling through Moscow with Bill Clinton or visiting George W. Bush at his Texas ranch, where Bush glowingly said of Putin: "I was able to get a sense of his soul."</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>But the Russian leader has grown increasingly isolated over the last decade, punished by much of the world for his 2014 invasion of Ukraine and Crimea, the downing of a Polish plane, a deadly nerve agent attack in the UK and far more atrocities.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>An attempted reset, complete with big red prop button, with Obama failed, and Russia was ultimately expelled from the Group of Eight nations.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>Before being elected in 2016, Trump claimed to have been "stablemates" with Putin ahead of an appearance on the US </span><em><span>60 Minutes</span></em><span>, though no evidence of the encounter ever materialised.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>After Trump came into office, Putin sought to restore his place on the world stage, through a marquee summit in Helsinki. That face-to-face meeting in 2018 only intensified a Russia cloud that would hang over Trump for the remainder of his first term and carry over into Putin's lone summit with Joe Biden in 2021. Eight months later, Putin launched another war with Ukraine that still rages on.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>It was that Helsinki meeting, where Trump met with Putin behind closed doors without advisers, that fuelled skepticism that is still alive today about his ability to stand up to the autocratic Russian leader. </span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>Trump faced an onslaught of bipartisan fury – and global condemnation – for accepting Putin's word over considerable evidence from the US intelligence community that Russia interfered in an American election.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>"We all think back to that really unsettling press conference in Helsinki where President Trump seemed to defer to Putin above the analysis of his own intelligence community," said retired US Admiral James Stavridis, former NATO supreme allied commander. </span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>"I truly hope that doesn't happen. I don't think it will."</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>It was a rare time in Trump's presidency where he admitted a mistake, saying after returning to the White House that he "realised there is some need for clarification" about his Helsinki remarks.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>But seven years later, after repeatedly striking a conciliatory tone toward Putin and touting his deep relationship with the Russian leader, Trump sounds far more skeptical at the prospect of reaching a deal over Ukraine. This pivot only came in May, when Trump suggested he would travel to Turkey to preside over a meeting with Putin and Ukrainian President Volodymyr Zelenskyy.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>"Nothing's going to happen until Putin and I get together, OK?" Trump said.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>When that meeting never materialised, and Russia intensified its bombing campaign on Ukraine, Trump began souring on Putin and lowering expectations for his long-standing promise to end the war.</span></div></div><div class="block-content"><div class="styles__Container-sc-1ylecsg-0 goULFa"><span>"I'm not happy with Putin," Trump said last month in one of his sharpest sentiments yet toward 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."</span></div></div>