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While Donald Trump’s second term has been anything but smooth sailing for Ukraine, it has not yet proved the unmitigated disaster many in Europe and Kyiv had been bracing themselves for.
So far, the reality on the ground has been a much more complicated saga, but one that reveals a great deal about the pitfalls of the America-first philosophy as it engages with actors outside the United States.
Despite returning to the White House promising swift peace in Ukraine, Trump has instead faced a revealing test of power and personality, and a complicated game of transactional geopolitics.
For the better part of a decade, the prevailing assumption about Trump’s foreign policy instincts could be condensed into a single word: Putin.
Since he first announced his intention to run for the presidency, Trump has exhibited a peculiar soft spot for the strongman in Moscow. He has consistently praised Putin’s “strength”, waxed lyrical about the symbiotic nature of their relationship, and repeatedly shrugged off accusations of election interference, routinely taking the Russian president’s word over the consensus of his own combined intelligence agencies.
The idea that Trump is indeed a Russian asset, if at least an unwitting one, is not altogether without merit. For much of his second term, his administration’s policies have afforded Russia breathing space to escalate its war on Ukraine.
The events of recent months, however, have complicated the picture. Trump’s actions over the last few weeks have put paid to the notion that he is Putin’s willing accomplice. If he is a puppet, he is now proving to be rather an uncooperative one.
The Art of the No-Deal
In essence, Trump’s relationship with Ukraine is not about values or even partnerships. It’s about leverage. That’s the through-line of his foreign policy: pursuit of the deal, contempt for diplomatic tradition, and a ruthless pragmatism where morality is secondary to results. Since returning to the office, he has sought to do what he believes he does best: strike a deal.
At the beginning of the year, he initiated talks with Putin almost immediately, believing that the fastest route to resolution would be found in offering Russia what it wanted most— a Ukrainian government willing to make concessions.
In Trump’s world, it’s a strategy that makes a great deal of sense. If getting a deal, not doing the right thing, is the ultimate goal, Volodymyr Zelenskyy, leading the smaller country with the smaller military, battered, bruised, and facing severe ammunition and manpower shortages, would be the natural party to lean on. This is where the cracks in Trump’s approach to geopolitics begin to show.
Zelenskyy, showing willingness to make accommodations for Trump’s victory plan, bent but would not break. The scale of Trump’s frustration with Zelenskyy’s refusal to roll over was clear for all to see when in February a now infamous press event in the Oval Office devolved into a shouting match in front of the world’s media with Trump and Vice President JD Vance doing most, if not all, of the shouting.
“You’re either going to make a deal or we’re out,” Trump blustered, before promptly dismissing Zelenskyy from the White House. “If we’re out, you’ll fight it out. I don’t think it will be pretty.”
He estimated, erroneously, that moving Zelenskyy would be easier than moving Putin. After all, Putin has long modelled the brand of authoritarian power Trump so admires; unyielding control cloaked in just enough legitimacy to keep a seat at the global table.
This miscalculation is revealing of Trump’s worldview and his fundamental approach to geopolitics. He holds neither diplomacy nor the nuance it typically requires in high regard, preferring to use blunt force to steam-roll his adversaries.
Donald is Drawn To Power Not The Person
Trump stands apart from other democratic, broadly liberal world leaders. His admiration for autocrats like Putin is neither accidental nor something he has ever made any particular effort to hide.
He has been unabashed in his expressed appreciation for power, particularly the unyielding, undemocratic kind, as well as those who wield it. Kim Jong Un, Bashar al-Assad and even the late Saddam Hussein and Muammar Gaddafi have all been the beneficiaries of strange and often surprising tributes from the American president.
There is, however, an important distinction to be made when it comes to these commendations. In the main, that it is these leaders’ power that Trump is venerating, much more the leaders themselves.
In many ways, Trump has been a gift to the press. His outrageous statements sell papers and keep audiences glued to their screens. As CBS CEO Leslie Moonves famously said in 2016, “It may not be good for America, but it’s damn good for CBS.”
In the rush to capitalise on clicks, networks and publications often omit, whether intentionally or otherwise, the context in which Trump’s outlandish comments sit. His notorious “good people on both sides” line, about the Charlottesville riots in 2017 in which a young woman was killed, was followed, almost in the same breath, by an explicit condemnation of neo-Nazis. It’s often these discarded portions of the quote that are the most overlooked – and the most telling.
When Trump praised Jong Un in 2015, saying, “you gotta give him credit,” he was referring specifically to the way the North Korean dictator managed to take control of powerful and conspiratorial “tough generals” after being thrust into leadership in his twenties. He also called the young dictator a maniac.
When Trump said he would give Assad an “A” grade for his leadership, or praised Saddam Hussein for his efficiency, he was also explicit in his condemnation of them as “really bad guys.” These are small nuances, but nuances that provide important context, and more importantly, insight into the Trump worldview.
The Psychology of the US President
The key to understanding Trump is not through the lens of ideology, but rather psychology. He is a creature of instinct, an incisive dealmaker – at least in his own estimation – forged in the crucible of the boardroom. He is neither a statesman nor an ideologue, but a pragmatist with a deeply transactional mindset.
As far as Trump is concerned, this nature has served him well. Regardless of the legitimacy or the mechanics of his getting rich, or even how rich he may or may not actually be, he is richer than most Americans could ever dream of.
Whatever one makes of his various bankruptcies, scandals, criminal cases, or his relationship with the truth, he has done what fewer than fifty people on the planet have managed to do: become the President of the United States. Not only that, he managed a barnstorming return to the White House – after being impeached twice and ending his first term in ignominy. This is not a defence of Trump, but rather a reflection of his belief that his instincts are vindicated by results.
Over the following months, while Kyiv showed a tentative willingness to engage, Putin remained unmoved. Zelenskyy, it seems, changed tack rather deftly, managing to ingratiate himself with Trump over several meetings, most notably during the funeral of Pope Francis in April. What was widely expected to be a brief and tense exchange yielded an unexpected result; the presidents appeared to successfully bridge the divide, with Trump describing the one-to-one as “very productive.”
As Trump and Zelenskyy began to repair their fractious relationship, Putin made his own erroneous estimation. While Zelenskyy’s new approach has been to cooperate, even offering to meet the Russian president in person at the on-again, off-again Istanbul talks, Putin has given exactly nothing— not a pause in bombing, nor a symbolic concession. He even broke his self-declared “unilateral truce” over Easter more than three thousand times in three days.
Being a strong negotiator is central to the image Trump works hard to project, and Putin’s continued aggression and refusal to engage meaningfully leaves Trump looking weak and ineffective, little more than an overeager go-between. It’s a significant blow to a man so invested in the appearance of control.
Since then, Trump’s messaging has undergone a marked shift. His public statements regarding Putin have grown colder, more caustic. Fulsome praise has given way to frustration and ire.
Now sounding like a man betrayed, he says Putin has thrown “a lot of bullshit at us, if you want to know the truth,” clarifying: “He’s very nice all the time, but it turns out to be meaningless.”
This rapidly evolving rhetoric belies the deeper pragmatic realignment underway. Last week, Trump overruled his Secretary of Defence and reversed the Pentagon’s unilateral decision to halt a shipment of Patriot missiles headed for Ukraine at the Polish border.
He is rejoining the NATO fold, agreeing to send billions of dollars of weapons to Ukraine via sales to the alliance, including long-range Taurus missiles. It’s a drastic about-turn given the apparent hostility between Washington and Kyiv only five months ago.
Zelensky Changed Tack and So Did Donald
As Zelenskyy began to play Trump’s game, Putin refused to follow the plan, and in Trump’s eyes, this isn’t just obstinacy; it’s an insult. It appears he is waking up to what other world leaders have known about Putin for a long time, even if they have done little of consequence to address it. He does not negotiate; he stalls and obfuscates all the while chipping away at his own goals in Ukraine, which include neither peace nor a deal. Meanwhile, Ukraine has endeavoured to forge ahead, developing drone technologies that lessen its reliance on inconsistent partners.
Trump’s rapidly evolving policy on Ukraine should not be mistaken for a wholesale abandonment of his instincts or a turn towards liberal interventionism. He remains deeply suspicious of entanglements, allergic to conventional diplomacy, and sympathetic to strength when it supports his goals.
Ever the pragmatist, this foreign policy realignment is simply a reflection of his overarching goal: to negotiate a deal that ends the conflict. His fracturing relationship with Putin has exposed that his admiration was always conditional; it was contingent on results.
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Returning to office, he sought to manage Putin by first managing Ukraine. Now he appears to have calculated supporting Ukraine is the more efficient way to manage Putin. It’s this strategic U-turn that affords a deeper glimpse inside the Trump worldview: NATO, the European Union, Ukraine, even Russia, are all pieces to be leveraged or leant on in pursuit of the deal.
If backing Zelenskyy better serves this purpose, he is willing to shift course. Whether this recalibration will last is another question. Changeability has so far been the one constant in Trump’s policy on Ukraine. For the moment, the direction of travel is clear.
Trump came to the table expecting a swift deal. Instead, he is confronting a reality that contradicts his experience of the boardroom: not every conflict ends with a handshake, not every adversary yields to bravado, and the admiration for power and control he shares with leaders like Putin does not always translate into deference.