ANCHORAGE, Alaska – President Donald Trump was criticized for siding with Russian President Vladimir Putin over the U.S. intelligence community in its assessment that Russia meddled in the 2016 election during Trump and Putin’s first and last stand-alone bilateral summit in Helsinki in 2018.

But while there are similarities between Helsinki and Friday’s highly anticipated meeting between Trump and Putin at Joint Base Elmendorf-Richardson in Anchorage, Alaska, including plans for a joint press conference after a one-on-one sit-down and lunch, the men and the political environment are different seven years later.

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Trump, for one, is politically emboldened after last year’s election, despite current domestic policy and political problems, from inflation to Jeffrey Epstein. Putin, who has also consolidated power, is now three-and-a-half years into a war he started with Ukraine that he expected to last days, though Russia has experienced momentum along the front lines in recent weeks. Ukraine, however, retains control of its skies after striking deep within Russia, in addition to Russian ships in the Red Sea, with its cutting-edge drone technology. 

Hudson Institute Center on Europe and Eurasia director Peter Rough underscored how Trump and Putin’s Helsinki summit was overshadowed by “what Trump now commonly refers to as the Russia hoax — the effort to delegitimize the 2016 election by smearing Trump as colluding with Putin.” 

“That political attack has not only lost its credibility but boomeranged on the Democratic Party,” Rough told the Washington Examiner. “So, this meeting will be different and the president will have more flexibility than he had then.”

Democrats and other foreign policy experts may disagree with Rough’s dismissal of the “Russia hoax,” but most would agree that Trump will arrive in Anchorage, a city equidistant between Washington and Moscow, in a position of relative strength but under pressure to negotiate a peace deal between Putin and Ukrainian President Volodymyr Zelensky.

Politically, Trump has to balance the competing interests of his MAGA base, which would prefer that the president extricate the U.S. from the war, with those of more establishment Republicans who have been encouraging him to support Ukraine by helping North Atlantic Treaty Organization allies supply Ukraine with weapons and by sanctioning Russia. 

Diplomatically, despite Trump trying to put America First, Ukraine and NATO allies are mindful that only the U.S. has the financial and military might to force Putin to the negotiating table.

And personally, after promising to end the war on the first day of his second administration, Trump has been candid about his desire to be awarded a Nobel Peace Prize. Simultaneously, Trump does not want to be played by Putin, with critics contending that Putin proposed Friday’s summit to prolong Trump’s deadline last week for more sanctions.  

In response, Trump and the White House started downplaying Friday’s summit, Trump and Putin’s first of Trump’s second administration, as an opportunity for Trump to ascertain whether peace between Russia and Ukraine is even possible, as opposed to negotiating a deal.

“I may leave and say, ‘Good luck,’ and that’ll be the end. I may say, ‘This is not going to be solved,’” Trump told reporters on Monday. “Probably in the first two minutes, I’ll know exactly whether or not a deal can be made.”

Trump then told another group of reporters there would be “very severe consequences” for Russia if Putin is not serious about a peace deal before describing Friday’s summit as “setting the table” for future meetings between himself, Putin, and Zelensky.

“If the first one goes ok, we’ll have a quick second one,” he said on Wednesday. “I would like to do it almost immediately, and we’ll have a quick second meeting between President Putin, and President Zelensky, and myself, if they’d like to have me there.”

Trump supporters point to Trump’s unpredictability as a strength regarding Putin, a former Russian intelligence officer and master manipulator, although questions have been raised about his mental health post-pandemic.

Regardless, Zelensky and NATO allies remain concerned Trump’s unpredictability could be a weakness if he undermines Ukraine and the NATO alliance as the president did this week when he complained about Zelensky being constrained by Ukraine’s constitution regarding his proposal for land swaps.

In an attempt to mitigate those concerns, Ukraine and NATO allies organized multiple phone calls this week with and without Trump to reiterate their redlines to the president, including prioritizing a ceasefire over discussions related to reciprocal territorial exchanges and long-term security guarantees as NATO member states prepare to spend 5% of their GDPs on defense.

Former Trump administration deputy national security adviser Victoria Coates, from his first administration, repeated that Trump had learned from Helsinki to approach Putin with “low expectations,” admitting “very little came out of Helsinki” other than the two respective national security councils meeting more regularly. 

Coates, now Heritage Foundation’s vice president, addressed Ukraine and NATO allies’ concerns about Trump’s past behavior toward Putin, arguing it is a “tactic” and “he does the same thing” with Chinese President Xi Jinping.

“It’s how you manage those relationships, and it’s completely consistent with his personality, but his actions are not appeasement or any sort of gift to Russia or China,” she told the Washington Examiner. “He’s been pretty tough on both of them. From his perspective, and I don’t want to be his psychiatrist, but it costs him nothing to say something nice in front of the international press, and he also knows it’s going to drive the international press mad, and that is entertaining. But watch his actual actions.”

Meanwhile, Russia has been prespinning Friday’s summit as an opportunity to reset the U.S.-Russia relationship, including through infrastructure, energy, and Arctic deals, as Putin conducts his own ally outreach to China and India. China and India are at risk of secondary sanctions should Trump impose them over their purchase of Russian oil. 

Trump met with Putin six times during his first administration. Nonetheless, former ambassador to Georgia William Courtney, who was a special assistant to former President Bill Clinton for Russia, Ukraine, and Eurasia, told the Washington Examiner “none of these encounters,” including Trump’s many phone calls with Putin, “appears to have yielded notable agreements or a lessening of tensions.”

Cato Institute defense and foreign policy studies director Justin Logan added Trump “seems to think that he can persuade Russia to stop fighting by force of his character, which has proved elusive thus far.”

Though “Trump is right that there is use in simply sitting down and getting a sense of where the Russian side is,” Logan told the Washington Examiner. 

Of Trump’s relationship with Putin, Brookings Institution defense and strategy chair Michael O’Hanlon told the Washington Examiner that Trump “genuinely has always liked [Putin] and respected his ‘toughness.’” 

“But one thing to remember about Trump is that he can change his opinion about people, for the better or the worse,” O’Hanlon said, with Trump recently expressing frustrations with Putin over the war.

To that end, perceived good relationships between U.S. presidents and their Russian counterparts have never resulted in long-lasting positive change between the two countries, according to Courtney, the former Clinton aide who was the deputy negotiator in the U.S.-Soviet defense and space talks too.

“Most famously, at Yalta in 1945, FDR hoped his relationship with Stalin might help on the issue of the USSR’s holding free elections in Poland,” the now RAND adjunct senior fellow said. “It did not. A communist-dominated government aligned with Moscow took power.”

With Putin demanding that Ukraine not become part of NATO, that Ukraine reduce the size of its military, that NATO allies no longer provide support to Ukraine’s armed forces, and that no NATO service members be deployed to Ukraine, Courtney recommended that Trump explore whether “Putin might need some relief from the war” as Putin relies on North Korea for man and firepower. 

“Russia’s civilian economy is starved for financing and technology, ordinary Russians are increasingly paying for the war through declining living standards amid high inflation, numbers of military killed and wounded are high, and Russia is having to pull older Soviet-era arms out of storage as more modern weapons have been destroyed,” he said.

For O’Hanlon, Brookings Institution’s foreign policy research director, “a disaster” for Trump on Friday would be him “buying Putin’s narrative about how eastern Ukraine is somehow innately Russian, selling out Ukraine along the way and deciding not to sanction Russia.” 

“A success is the beginning of a compromise on reasonable parameters for ending the war, along the lines suggested by European leaders,” he said.

BESSENT PRESSES EUROPE TO ALIGN WITH TRUMP’S TARIFF STRATEGY TO END UKRAINE WAR

Hudson Institute’s Rough continued that “if Putin balks, Trump can either walk away from the negotiations and-or hit Russia with greater economic pressure.” 

“I think the summit will be a success if it forces Putin to choose between a ceasefire or sanctions,” the former George W. Bush White House Office of Strategic Initiatives associate director said. “The next step will be for the U.S. to coordinate closely with our allies as the talks unfold and script our next steps accordingly. Putin loves to sow division and we should be on guard for that.”