Why Ukraine thinks it can still win over Donald Trump

The relationship between Donald Trump and Ukrainian President Volodymyr Zelenskyy has always been, to put it mildly, a little complicated. In 2019, there was the “perfect phone call,” in which Trump allegedly leveraged US aid to Ukraine to pressure Zelenskyy to investigate Hunter Biden. And the more recent awkward meeting in New York during the 2024 presidential campaign in which Trump talked about his good relationship with Vladimir Putin in front of the man whom the Russian leader had reportedly tried to kill. 

But Trump has also expressed some grudging admiration for Zelenskyy, a fellow TV star-turned-politician who has demonstrated he knows how to close a deal. “I think Zelenskyy is the greatest salesman in history — every time he comes into the country, he walks away with $60 billion,” Trump said at a rally in September. 

But after Trump’s return to the White House, Zelenskyy may now have his toughest “sales” job yet. Zelenskyy quickly congratulated Trump on his victory and the two held an initial phone call last week which was joined — in a likely sign of strange things to come — by Elon Musk, and described by Ukrainian officials as somewhat reassuring. Trump also reportedly spoke with Putin over the weekend, according to the Washington Post, though the Kremlin has since, confusingly, denied it. 

The conventional wisdom is that Trump’s election is a major setback for Ukraine, coming at a moment when it is already losing territory and troops at a slow but steady rate to Russia’s relentless advance and when its civilian population is likely in for another brutal winter due to Russian strikes on the country’s energy grid. Opposition to support for Ukraine has become a core position of the Republican Party’s MAGA wing, and GOP opposition earlier this year held up a major aid package to Ukraine for months. 

Trump himself has blamed Zelenskyy for starting the war. He has also promised to end the fighting in 24 hours once in office. It’s not clear how he plans to do that, but Vice President-elect J.D. Vance has suggested it would involve freezing the current front lines in place and Ukraine declaring its neutrality and giving up its ambitions to join NATO. (Though Zelenskyy has mostly avoided directly criticizing Trump, he has described Vance as “too radical.”) 

Ukraine’s government would view a “deal” like this as full surrender, and argues, with reason, that Russia shouldn’t be trusted to maintain a ceasefire: Putin could always try again to take more territory or even Kyiv itself after a pause to replenish his losses. 

But while the conventional wisdom may be true that Trump’s win is a blow to Kyiv, Ukrainian leaders are still expressing some cautious optimism that they can work with the new administration. The pitch from “the greatest salesman in history,” however, is going to have to change. 

Selling Ukraine

One thing you likely won’t be hearing as much: talking points about defending democracy or upholding the rules-based international order, which both Zelenskyy and Joe Biden frequently used over the last two years since Russia’s invasion. Such rhetoric is likely to fall flat with Trump, given his often nakedly transactional approach to foreign policy and general fondness for authoritarian leaders. 

Speaking on a press call hosted by the think tank German Marshall Fund on Friday, Hanna Hopko, a former Ukrainian parliament member and co-founder of the International Center for Ukrainian Victory, an advocacy group, made the change clear. “We understand that with Trump, it’s not about philosophy,” she told reporters. “It’s not talking about a rules-based order. It’s about a very pragmatic approach.”

That’s probably why Zelenskyy has lately been emphasizing that Ukraine is “rich in natural resources,” including critical minerals like titanium, graphite and lithium, which could be vital for the green energy transition. It’s a line that has been echoed by Sen. Lindsey Graham (R-SC), one of the few close Trump allies who is also a staunch Ukraine supporter.

Noting that Trump has said in the past that Russia should be allowed to keep the Crimean peninsula, which it annexed in 2014, Hopko argued, “It’s important to explain to Trump, who likes to be a winner, that Crimea has huge potential for natural gas extraction.” 

This type of logic has worked on Trump in the past: During his first term, he claimed he ultimately decided to keep US troops in Syria, despite several pledges to withdraw them, in order to “keep the oil” in the region.

Ukrainian officials also believe they can portray themselves as good for American business. “I’ve heard that Republicans stand for the defense industry. We’re bringing value to the defense industry of the US,” Oleksandr Kamyshin, Ukraine’s minister of strategic industries, told a gathering on the sidelines of the NATO Summit in Washington over the summer. More than $68 billion of the money allocated for Ukraine has been spent on the US companies. Hopko also noted that Ukraine’s advances in drone warfare and autonomous weaponry can benefit the US military through technology-sharing and battlefield testing. 

John Conway, director of strategy for Republicans for Ukraine, an advocacy group, said that supporters of Ukraine’s cause should emphasize the threat a victorious Russia would pose to the US itself. “Just recently [Putin’s] secret operatives tried to blow up civilian airplanes bound for our airports and called in bomb threats to disrupt our elections,” Conway told Vox by email. “When Putin loses, America wins. Ukraine can make Putin lose.”

The other reason Trump may end up extending support for Ukraine rather than making a deal is that it’s not clear whether Putin is interested in peace at a time when he likely feels he has the upper hand in the war. The choice may not be between ongoing war and negotiations but between ongoing war and Ukrainian defeat — something an always image-conscious Trump may not want to see under his watch. 

David Kramer, a former US assistant secretary of state under George W. Bush, said the prospect of a full Ukrainian defeat happening as a result of his actions might give Trump pause. “The last thing that Trump is going to want there would be a chaotic collapse, a la Afghanistan 2.0,” he said. (Though Trump’s first administration negotiated the agreement that led to the US withdrawal from Afghanistan, he repeatedly blamed the Biden administration for its handling of the chaotic pullout.)

Will Trump listen? 

Ukrainian officials and their Western advocates often point out that for all his kind words for Putin and tense relationship with Zelenskyy, it was Trump who agreed to sell Ukraine anti-tank Javelin missiles — something the Obama administration had declined to do. Javelins would later play a pivotal role in Ukraine’s ability to resist the initial Russian invasion in 2022. (This was likely part of the reason why Russia’s official reaction to Trump’s return was a lot less jubilant than it was in 2016.) 

More recently, Trump was convinced to give his congressional allies blessing to approve a Ukraine-aid package earlier this year after the money was structured as a loan rather than a grant — a sign, perhaps, that appealing to his business instincts can be a winning strategy. 

Whether Ukraine’s new pitch will work could also depend on who ends up in Trump’s Cabinet. Ukrainians might have hoped for a return of former Secretary of State Mike Pompeo, who has visited Ukraine and has advocated for providing it with more advanced weapons systems. Trump, though, has already ruled out a role for Pompeo in the new administration, and early indicators are that Republican hawks may not have a home in the new administration. 

Former national security adviser Robert O’Brien, who unlike his two predecessors in the first Trump administration, didn’t subsequently condemn Trump, is thought likely to return to a senior role this time. O’Brien argued in an article in Foreign Affairs earlier this year that Trump’s strategy would be to “continue to provide lethal aid to Ukraine, financed by European countries, while keeping the door open to diplomacy with Russia—and keeping Moscow off balance with a degree of unpredictability.” O’Brien also advocated for increasing NATO’s military presence in Eastern Europe, close to Russia’s border — a step guaranteed to raise Putin’s ire.  

It’s not at all clear that Trump shares the views being ascribed to him by O’Brien, but it’s a sign that there is likely to be a wider range of opinion in the new administration’s foreign policy team than many might think. 

It’s not going to get easier for Ukraine

The reality is that a reckoning on US support for Ukraine might well have taken place even if Vice President Kamala Harris had won the presidency, if only because of growing opposition in Congress as well as Russia’s undeniable battlefield progress, with Moscow willing to sacrifice tens of thousands of soldiers for its war goals. It’s not only MAGA figures who are pushing for compromise with Russia — some members of Washington’s foreign policy establishment increasingly are as well. 

It’s also worth pointing out that while Biden was a staunch advocate for the Ukrainian cause, officials in Kyiv have often expressed frustration with his administration’s delays in providing new weapons systems and capabilities, motivated by what they see as an unwarranted fear of escalating war with a nuclear-armed Russia. 

“Every time we ask for something, we get it months or a year later when it won’t make as much of a difference as it would have before,” parliament member Oleksandra Ustinova told Vox in June. 

Some advocates even hope Trump could take the gloves off, greenlighting tactics like long-range strikes into Russian territory with American weapons, something the Biden team was reluctant to approve. On the other hand, Trump, like Biden, has warned of the specter of “World War III.” In a September op-ed, the president-elect’s son, Donald Trump Jr., and his new ally Robert F. Kennedy Jr. advocated negotiations with Russia in order to avoid nuclear war. Those escalation fears are unlikely to disappear. 

Ultimately, the Ukrainians will hope for the best and try to work with Trump’s team because there’s little other option. Trump’s relationship with Putin and past statements about the war don’t give much cause for optimism, but ironically, the thing the Ukrainians now seem to be counting on is his unpredictability