Reports that former President Donald Trump continued to communicate with Russian leader Vladimir Putin after leaving office seem likely to encourage new attention to Mr. Trump’s claim that he has an undefined plan to end the Ukraine War “before I even become president.” Many commentators assert that Trump’s plan could only succeed if the United States forces Kyiv into unilateral territorial concessions to Russia. That may well be true, but it ignores an important question: would Moscow accept Trump’s deal?

Many in Washington—and the media—assume that Trump plans to give up and that Putin would readily agree to that. This simplistic thinking wholly sets aside Trump’s record as president, including his record in seeking big deals, which is mixed at best. It likewise sets aside Trump’s highly visible and somewhat desperate quest for personal validation and public triumph through successful deal-making. Recall his 2019 statement that he “would get a Nobel Prize for a lot of things if they give it out fairly, which they don’t.”

Indeed, in retrospect, Mr. Trump entered office in 2017 on a mission to prove that he could stare down the world’s toughest leaders, including Putin, China’s Xi Jinping, Iran’s Ali Khamenei, and North Korea’s Kim Jong-un, and walk away with victories. Consider how the former president attempted to use varying combinations of flattery and threats to redefine the U.S.-Russia relationship, rebalance the U.S.-China trade relationship, compel Tehran’s leaders to abandon their nuclear weapons program and roll back North Korea’s nuclear weapons development. With the partial exception of his diplomacy with China, which yielded an agreement that Beijing did not fulfill, these efforts failed. 

The former president’s most impressive diplomatic success was the Abraham Accords, which normalized relations between Israel and the United Arab Emirates, Bahrain, and Morocco. This was a major accomplishment in the Middle East, which nevertheless remains tortured by its divisions. Trump’s peace agreement with the Taliban, while significant in ending the long, costly, and largely unsuccessful U.S. war in Afghanistan, was much less fruitful, in no small part due to America’s weak negotiating position. And following the Biden administration’s disastrous handling of the U.S. withdrawal, few are heaping accolades on Trump for his contribution to getting America out.

Those troubled by Trump’s claims about his ability to settle Russia’s war on Ukraine appear fixated on the possibility that his approach to a deal would mirror his administration’s negotiations with the Taliban (weak U.S. leverage, considerable concessions, bad outcome) or China (untrustworthy partner makes a deal and then reneges on its commitments). But what if Trump’s approach instead follows the trajectory of his earlier efforts at deal-making with Moscow or, alternatively, his approach to Tehran or Pyongyang?

In his earlier effort to engage Vladimir Putin, Trump appeared to understand neither what his own side (various domestic constituencies and U.S. allies) wanted nor what Putin wanted. This prompted domestic attempts to undercut his approach, including acts of Congress, leaks, and investigations, as well as resistance by U.S. allies. At the same time, Trump made no headway with Putin, who saw little for Moscow to gain in engaging him. 

Trump leaned more on pressure and less on charm in negotiating with North Korea’s Kim and especially with Iran’s leaders. Yet, in each of these two cases, he likewise appears to have failed to understand his counterparts’ motives and goals. With respect to Tehran, he also seems to have drastically overestimated Washington’s unilateral leverage over Iran. Thus, the United States was arguably worse off after abandoning the Obama administration’s Joint Comprehensive Plan of Action and Trump’s historic but very poorly executed attempt to talk directly to Kim. 

The core of Trump’s problem in negotiating the grand international agreements that he yearns for may well be that his experience making real estate deals—often with the quasi-dictatorial heads of other privately-held companies—is less applicable to diplomacy than he thinks it is. As Ronald Reagan famously said of liberals in 1964, “The trouble…is not that they’re ignorant; it’s just that they know so much that isn’t so.”

Real estate development is undeniably complex, especially in a place like Manhattan, and requires not only working with one’s counterpart but also with local governments, businesses, and residents, among others. That said, when a deal falls apart, there will always be another potential project and a new potential partner. Major international negotiations have far more angles and stakeholders, and their collapse has far higher costs. These big deals are also much rarer, and if they don’t work the first time, the conditions that are needed might never exist again. 

This points to central questions that few have asked: what is Trump’s deal? More precisely, since the former president seems to have little interest in Ukraine’s independence or territorial integrity, what is it that he expects Putin to deliver in exchange for those—and why does he think that Putin would do so? Trump will not win the Nobel Peace Prize or secure praise from anyone other than his most loyal backers for turning Ukraine over to Russia without getting something in return. 

What Trump wants is uncertain. Still, his first-term deal-making reveals something about his priorities—competing with China and addressing the nuclear dangers that North Korea and Iran pose to America and its allies. Less obvious is to what extent Vladimir Putin would be willing to help with any of that. If Donald Trump had discussed this with Putin, an allegation that many may reflexively believe without any specific evidence, perhaps he would have had good reasons to think that the Russian leader was willing to negotiate. If he has not, why does he think that Putin could agree? Russia’s Foreign Ministry spokeswoman publicly poured cold water on a quick peace deal over the summer; she said that “it’s necessary to separate pre-election rhetoric from statements by government officials vested with the appropriate powers” and added, “Let’s be realistic.”

No less important is whether Trump thinks such a deal could work. How would he synchronize U.S. and Russian actions to ensure that Putin lived up to his end of the agreement? What mechanisms would he establish to ensure that Moscow didn’t change course later? Would Putin agree to a deal without Congress removing sanctions? Could Trump get Senate and House support for that? What would Ukraine and America’s NATO allies do while this is underway? While Trump-era officials have set out a plausible forecast of Trump’s strategy, critical details are missing.  

If these details exist in Trump’s mind, or the minds of his key advisors, and if they have solid reasons to think that Putin will sign on, perhaps the dealmaker-in-chief could successfully sign an agreement with his Russian counterpart. If not—which seems more probable—Washington may witness a collapsed attempt to engage Putin after the hypothetical new U.S. president reiterated his past threat to Russia: “If you don’t make a deal, we’re going to give [Ukraine] a lot. We’re going to give them more than they ever got, if we have to.” This raises a final question: what is Mr. Trump’s plan B?

Paul J. Saunders is President of the Center for the National Interest and a member of its board of directors. His expertise spans U.S. foreign and security policy, energy security and climate change, U.S.-Russia relations and Russian foreign policy, and U.S. relations with Japan and South Korea. Saunders is a Senior Advisor at the Energy Innovation Reform Project, where he served as president from 2019 to 2024. He has been a member of EIRP’s board of directors since 2013 and served as chairman from 2014 to 2019. At EIRP, Saunders has focused on the collision between great power competition and the energy transition, including such issues as energy security, energy technology competition, and climate policy in a divided world. In this context, he has engaged deeply in energy and climate issues in the Indo-Pacific region, especially U.S. relations with Japan and South Korea. His most recent project at EIRP is an assessment of Russia’s evolving role in the global energy system.

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