Trump Meets Putin: What Could Go Wrong – or Right?

Can the inveterate dealmaker in the White House pull another rabbit out of his hat?

President Donald Trump will meet with Russia’s Vladimir Putin today in Alaska. And after scoring so many victories over the seven months since his inauguration, this could be the biggest foreign policy risk of his second presidency since the bombing of Iran. As Trump sits down to talk turkey with the Russian president, the odds against forging a deal between Putin and Ukrainian President Volodymyr Zelensky appear overwhelming. But then, that has been the case with the five ceasefires and peace deals the president has already forged.

Neither side appears to have budged. Putin and Zelensky have both publicly issued non-negotiable territorial demands that are entirely unacceptable to the other side. And that is on top of security guarantees demanded by both. Putin has been adamant about maintaining control of the areas in Ukraine he has taken over and annexed. Zelensky says he will not cede an inch of Ukrainian territory. So what is the basis for a deal to end the three-year-old war? Where does this process go with both sides so dug in?

Moral Equivalence?

Trump and his envoy, Steve Witkoff, have been working diligently to end the fighting that has cost the lives of more than one million soldiers and citizens and bring about a lasting and workable peace. This involves the need to avoid expressing moral judgment about Putin’s shocking brutalization of a country that did nothing to provoke the Russian invasion. And while Trump has recently expressed frustration with Putin’s continued attacks on soft Ukrainian targets, which many rightly consider war crimes, he has refused to issue a blanket condemnation of the unspeakably cruel Russian offensive, citing the need to be a neutral arbiter in his quest to broker a sustainable ceasefire and peace deal.

Russia has been holding the upper hand in recent fighting, particularly in eastern Ukraine, where it continues to control the industrially and economically crucial Donbas region along the border between the two countries. Does Putin thus believe he is operating from a position of sufficient strength to convince Trump, and later Zelensky, to offer up a more favorable deal than he might have previously expected?

Given Putin’s annexation of the Crimean Peninsula in 2014 and the full-scale invasion of his country in 2022, the Ukrainian president is equally stubborn about recovering control of Donbas. “For the Russians, Donbas is a springboard for a future new offensive. If we leave Donbas of our own accord or under pressure, we will start a third war. I am not going to surrender my country because I have no right to do so,” Zelensky said on Wednesday (August 13).

Security demands are another huge sticking point that could stall negotiations. Putin has said Ukraine must shrink its standing army, which seems a near-impossible demand already publicly rejected by Zelensky, and receive assurances that it will never be admitted into NATO, a far more realistic prospect since Trump appears to agree. Zelensky continues to push for NATO membership, which would guarantee protection from the alliance’s 32 member states, but that would inevitably drive Putin away from the negotiating table.

The Putin Economy Coming Apart

Is Putin coming to the table from a position of strength or weakness? This war of attrition has progressed at a snail’s pace, far from the swift and decisive victory Putin likely expected. Thus, on top of the deaths of hundreds of thousands of troops, the cost to the Russian economy has been enormous. It has forced Putin to transform his country into a warmaking machine to account for the massive and ongoing drain on military assets.

But it may be that Putin called for the meeting with Trump because of the pressure Trump has been applying in trade negotiations with countries, particularly India, which depend on Russian oil. With his home functioning virtually as a single-commodity state, Putin likely fears the loss of this crucial foreign oil income that stands to make or break his economy. Russia’s oil revenues have been dropping precipitously since the war started due to both economic sanctions and persistent Ukrainian drone strikes against Russian oil refineries.

Another live possibility is that Putin is merely attempting to buy time by agreeing to meet with Trump without actually being prepared to offer any concessions. But if that becomes evident to the American president, he will likely walk away. Trump famously prizes winning, and any indication that at least a ceasefire – like the ones Putin has repeatedly accepted, then violated – is not in the cards, expect him to stiffen the already severe economic sanctions on his Russian counterpart, call it a day, and let the warring parties figure it out for themselves.

A journey of a hundred miles begins with the first step. And today’s meeting is just that, an initial sit-down in which Trump and Putin will feel each other out. And while Trump said this week that he should know whether Putin is serious about a ceasefire in the first two minutes of their meeting, rest assured that actual peace will take time, perhaps a long time, even if Putin appears more flexible than expected. This 47th president has already forged multiple ceasefires or peace deals between bitter enemies – Israel and Iran, Israel and Hamas, India and Pakistan, Thailand and Cambodia, and most recently, Azerbaijan and Armenia. Can he pull another rabbit out of his hat?