The Fiasco of Transactionalism: How and why Putin outmanoeuvred Donald Trump

It now seems likely that Donald Trump will enter the annals of diplomacy not for the spectacular peace in Ukraine he promised during his election campaign and hoped would earn him a Nobel Peace Prize, nor even for the Abraham Accords, which marked a genuine breakthrough during his first term. Instead, Trump’s legacy may be defined by his contradictory, inconsistent, and at times scandalously baffling negotiations with Vladimir Putin, in which he appears to have been manipulated and ultimately undone by his own ambitions.

European leaders were reportedly stunned after speaking with Trump following his 19 May call with Putin, according to Axios, citing individuals present during the conversation. Trump told them that he had just agreed on the immediate commencement of direct talks between Russia and Ukraine. When Zelensky, apparently surprised, remarked that such talks were already underway, Trump had no reply, one participant recounted. Trump also stated that, contrary to the previously agreed position, he no longer insisted on a 30-day ceasefire and had no intention of exerting further economic pressure on Putin.

Trump's adolescent and enthusiastic post about his conversation with Putin offers little clarity on the outcome of their two-hour conversation. In contrast, the Russian interpretation was set out in detail by Putin’s aide, Yuri Ushakov: the discussion was described as extremely constructive; the sides agreed on a prisoner exchange and the development of bilateral relations, including economic cooperation, as well as engagement on various international issues, particularly the Iranian question. This comment highlights that the negotiation process between Washington and Moscow is now viewed as proceeding independently of the Ukrainian settlement and progressing in a highly constructive manner. Meanwhile, talks between Moscow and Kyiv are expected to take place without US involvement – and to succeed, thanks to the supposed complete mutual understanding that prevails in Trump’s relationship with the Kremlin. The Russian delegation has been pushing for this split in the talks, which would push the issue of Russian aggression against Ukraine and ending the war to the sidelines, since the first Russian-American meeting in Riyadh. But Zelensky and the European coalition supporting Ukraine have been keeping Trump from taking this step for three months.

In his conversation with European leaders, Trump also said that he had proposed Putin draw up a ‘memorandum’ to serve as the basis for a peace agreement. And this handing over of mediator functions to the aggressor in a peace process he himself initiated may well become Trump’s new trademark in the annals of diplomacy.

Trump's four attempts

The phone call with Putin marked Trump’s fourth attempt in as many months to achieve a breakthrough in relations with the Russian dictator.

The first negotiation track began with a phone call initiated by Trump on 12 February. After the call, he wrote that US-Russia negotiations would begin immediately and expressed hope for swift meetings with Putin in Moscow, Washington, and Riyadh. The Riyadh track continued with a meeting between delegations led by foreign ministers Sergey Lavrov and Marco Rubio, but reached a dead end by the end of March after a failed ceasefire 'in the air', which resulted in intensified Russian bombing of Ukrainian cities.

On 30 March, Trump threatened to impose 25% tariffs on Russia. However, just days later, on 3 April, a meeting in Washington between special envoys Steve Witkoff and Kirill Dmitriev launched a new negotiation track. This one was marked by a higher degree of 'intimacy'. Without aides, and even without his own interpreter, Witkoff became a direct channel for relaying the Kremlin’s wishes straight to Trump. Witkoff travelled to meet Putin twice in April, and Trump once again brimmed with optimism, writing on his social media platform that a breakthrough was imminent. However, despite the White House's promises and concessions (official recognition of Crimea as Russian and the lifting of all (!) sanctions imposed since 2014), this track also ended in failure by the end of the month, when Moscow rejected the ‘final peace proposals’ of the United States. Members of Trump’s administration began once again to speak of changing their approach to Moscow if it would not agree to a 30-day ceasefire.

On 10 May, Ukraine’s European allies issued Russia an ultimatum to cease hostilities, warning that failure to comply would trigger harsher sanctions. Yet after Putin’s late-night press conference, in which he hinted at a possible meeting with Trump in Istanbul, the ultimatum was quietly dropped, and Trump declared he was ready to attend a meeting that would end the 'bloodbath.' But just 12 hours before the scheduled talks, Putin made it clear he would not be going to Istanbul (→ Re:Russia: The American Dream). Thus, Trump's third attempt failed.

Nevertheless, like a smitten lover unable to accept rejection and clinging to the hope that next time he will win over the object of his fixation, Trump spoke the very next day about how, in order to achieve progress in the negotiations on Ukraine (yes, that's right!), he needed to meet with Putin in person. But again, instead of a meeting, he only received a phone call, which nevertheless left him in a state of youthful excitement.

The recurring pattern behind Trump’s four failed negotiation tracks is plain to see. Each new round begins at the initiative of the American president; at the outset, Washington announces new concessions to Moscow, along with promises of further benefits should talks succeed. When met with the Kremlin’s intransigence, Trump begins cautiously threatening sanctions. Negotiations are then broken off, and the White House searches for diplomatic ways to relaunch the process in a new format, more closed and personal, to avoid having to carry out its threats. This behaviour directly contradicts not only Trump’s own proclaimed negotiation style, which emphasises the importance of speaking from a position of strength and then engaging in transactional deal-making, but also the fundamental principles of diplomacy itself, in which consistency and the credibility of threats are considered sacrosanct.

Four theories

There are several interpretations that claim to explain Trump's diplomatic anomaly. The first is conspiratorial. According to this theory, Trump is beholden to Putin due to compromising material gathered during his numerous trips to the Soviet Union and Russia in his pre-presidential, property-developer days. As with all conspiracy theories, it is supported by the argument that the absence of concrete evidence does not disprove the hypothesis. Hidden leverage is valuable precisely because it is hidden. However, the real reason for the persistence of this theory lies elsewhere: it is compelling because explaining Trump’s behaviour based on known assumptions, conditions, and rational logic proves exceedingly difficult.

The second theory, by contrast, is built on the notion of 'geopolitical foresight'. It, too, has conspiratorial overtones: namely, that the conflict with the West, stoked by Moscow, is in fact a trap set by Beijing for the United States. The aim is to drag the West and the US into a broad confrontation with Russia. The ultimate beneficiary of this conflict would be China, which, by staying out of the confrontation directly and avoiding its massive costs, would emerge as the dominant geopolitical power in the endgame. In some sense, this narrative mirrors how the United States solidified its position as the world’s leading superpower during the Second World War. This threat, widely discussed among experts in the early years of the conflict, has been revived by Trump’s allies in recent weeks.

The weakness of this theory is that throughout 2023–2024, amidst limited arms supplies to Ukraine, Putin showed little intent to escalate. On the contrary, critics of the 'China conspiracy' theory argue, his inability to achieve military victory and the firmness of the Western coalition acted as constraints, forcing him to focus on the Ukrainian theatre. Meanwhile, Trump’s negotiation strategy allowed Moscow to turn the issue of Ukraine into a source of division within the Euro-Atlantic alliance. As a result, Putin’s threats against Europe and signs of preparations for broader conflict have taken on an increasingly demonstrative character. By weakening transatlantic unity, Trump is emboldening Putin to escalate. Yet in the event of a wider European war, the likelihood of the US being drawn in would be far greater than it is now.

Furthermore, proponents of the traditional ideology of containment argue that the war in Ukraine is a rehearsal for a potential attack on Taiwan by China, a decision on which will be made depending on how effective and strong the West's response to Putin's attack on Ukraine will be. According to this logic, the weakness shown by the West and Trump also brings escalation closer, rather than pushing it further away.

The ‘China conspiracy’ theory also fails to explain Trump’s refusal to use even the relatively safe but strategically potent tool of tougher sanctions against Moscow. This would have been a desirable instrument for both deterring Russia and showcasing US negotiating strength. The strategy appears all the more viable given current oil market conditions, which are particularly favourable for implementing such measures.

The third theory is the notorious ‘wedge’ theory, that is that Trump dreams of driving between China and Russia. Arguments discrediting the viability of this strategy have been made repeatedly (→ Re:Russia: A Lame Alliance of Victory), and in both Moscow and Beijing, it is a source of mockery. Four months of negotiations conducted by Washington from a position of weakness have only served to strengthen the Russia–China alliance, clearly signalling to the Kremlin where true power, strategic consistency, and the credibility of promises and threats reside — in Beijing, not Washington. In effect, Trump’s wedge strategy has been reversed; rather than dividing his adversaries, it has been used by them to manipulate him. As Michael McFaul and Evan Medeiros have noted, the real consequence of this strategy so far has been to drive a wedge between the United States and its long-standing and reliable allies in Europe – all in pursuit of the illusory favour of a geopolitical rival.

A final interpretation of Trump’s behaviour is the 'isolationist' one. From this perspective, the United States should withdraw from all conflicts in which it is defending the interests of others, including Ukraine and the Middle East. Since the attempt to exit the conflict while simultaneously halting the war has failed, Trump, it is argued, should simply abandon support for Ukraine. While isolationists do have a presence within Trump’s inner circle, their strategy is unlikely to be implemented in any consistent way in today’s interconnected world. The space vacated by a US withdrawal would naturally be filled by China, which would gradually absorb the architecture of international alliances and security guarantees.

The Ukrainian conflict could well be the first instance of this kind. Were the United States to truly withdraw from Ukraine and from the peace process, a turn by European leaders towards Xi Jinping, as a mediator and guarantor of an agreement with Putin that preserves Ukrainian sovereignty, would seem not just plausible, but almost inevitable. Beijing, in turn, would be highly motivated to showcase its mediating abilities and the potential of Chinese arbitration in a case where the US has proven ineffective. At this stage, Xi Jinping likely holds more leverage over Russia than Trump does.

Trump vs. Trump: the failure of transactionalism

As we previously noted, back in early February, Trump rejected Keith Kellogg's plan, which involved putting pressure on both sides to find a compromise.

That plan involved applying pressure to both sides in pursuit of compromise: threatening Kyiv with an end to arms deliveries, while simultaneously warning Moscow of increased support for Ukraine and tighter sanctions (→ Re:Russia: Three Hundred Days in Search of a Silver Bullet). On 6 February, Kelogg outlined the plan in an interview with the New York Post, and on 12 February, at Trump's initiative, his first conversation with Putin took place.

It appears that at that point, Trump had formulated an alternative vision for peacemaking. Essentially, he offered both Kyiv and Moscow the prospect of economic cooperation with the United States. He believed this offer would appear so attractive that it would compel both parties to compromise and make peace. Judging by Trump’s own post on 19 May following his call with Putin, he still maintains, albeit likely more for show than out of genuine belief, that this strategy is viable.

Such a plan undoubtedly appeals to Trump due to its stark contrast with Biden’s strategy, its deeply transactional spirit, and its exclusion of any need to exert pressure on Moscow. Notably, it also avoids further discussions about a new military aid package for Kyiv once the Biden administration’s current package runs out mid-year. From that moment onwards, any mention of additional aid to Ukraine becomes a complete taboo within Trump’s team, and Kellogg, who had advocated for using that leverage, is entirely sidelined from the negotiations for a full three months.

Judging by all appearances, the new plan was developed by a very small circle of people close to the president, which had a critically negative impact on its quality. In any case, its first step – a draft agreement with Ukraine on rare earth metals – resulted in a fiasco: Ukraine simply does not have any significant reserves of these metals (→ Re:Russia: Shackles, Chimera or Marshall Plan?). The final agreement between the US and Ukraine, although not quite as crudely colonial, is also notably lacking in detail. As for the economic proposals intended to entice Moscow, we know even less, but they, too, appear to have been largely chimerical in nature (→ Re: Russia: Arctic Blitz; Re: Russia: Gas Temptation).

At the same time, Moscow's unyielding stance, insisting on its maximalist demands on all three negotiating tracks, which effectively amount to Ukraine's capitulation, was underpinned by the Kremlin's confidence that the Russian army would finally be able to turn the tide on the battlefield in 2025. Putin was, in effect, selling Trump his future victory, and the main instrument of pressure on Trump became Trump himself. More precisely, it was his unwillingness to provide Ukraine with new military aid that made Putin's hopes of realising his military advantage seem realistic.

Trump's fear of having to approve new arms deliveries allowed Putin to gradually transform him from a powerful decision-maker confidently stopping the war, into a supplicant who made threats only to renounce them the next day and offer new concessions, and then waiting for days for the Russian dictator's response – whether he would agree to the meeting or not – only to receive a dismissive refusal.

A widely circulated myth claims that Putin’s tactic of using an opponent’s strength against them was inspired by martial arts. But a more plausible explanation is his experience as a secret service agent, skilled at finding the weak spot of his target and pressing on it, not letting them get away until the goal of recruitment is achieved.

In any case, as long as new military aid to Ukraine remained taboo for the Trump administration, Putin remained deaf to the transactional promises and requests of the American president. Eventually, this forced Trump to acknowledge his own impotence, abandon his boastful pledges, and all but literally leave Ukraine at the mercy of the aggressor.

One of Trump's central, if not primary, motives over the past year has been his fierce criticism of Biden's Ukraine strategy (and the Europeans who supported it). A peace deal, struck in one or even 100 days, was meant to be proof of its total failure and a demonstration of the success of Trumpian transactionalism. However, four months of appeasing an aggressor, undermined alliances, empty threats, and fruitless concessions now appear to be elements of a spectacular fiasco, and a resounding triumph for Kremlin strategic diplomacy, which refused to accept a 'pig in a poke' as a sign of strength or geopolitical foresight.