A Former UN Mediator Reveals: Trump’s Ukraine Strategy Might Be Smarter Than It Seems

  • maskobus
  • Aug 10, 2025

The Complex Art of Transitioning from War to Peace

War is often viewed as a cowardly escape from the problems of peace, as highlighted by Thomas Mann, one of Germany’s leading writers of the 20th century. Indeed, transitioning from war to peace is an intricate process that demands courage, sacrifice, and strategic planning. This complexity becomes even more evident when examining the efforts made by Donald Trump to bring about peace in Ukraine.

Trump’s approach to achieving peace in Ukraine has been marked by shifting timelines, causing confusion and criticism within the West. Many argue that his reliance on Russia’s willingness to pursue peace is naïve, while also criticizing the pressure placed on Kyiv, the victim of aggression. Additionally, there have been rapid and unpredictable changes in the US position, further complicating the situation.

Despite these challenges, it is worth considering that the US action on Ukraine has been a textbook example of negotiating theory. However, this toolbox is gradually being exhausted, with Russia emerging as the main obstacle to peace. Steve Witkoff’s mission to Moscow may represent a final opportunity to move towards an actual peace settlement.

A Strategy for Mediation on Ukraine

Initially, there was a clear plan or conflict analysis leading to a mediation strategy. In April 2024, before the change in the US Administration, retired Lt General Keith Kellogg and former senior CIA analyst Fred Fleitz published an analysis of the war. They concluded that no side could fully achieve its military objectives through force. Both sides were persuaded that if they held their nerve and kept fighting, they might still achieve their key aims.

Ukraine refused to accept losing nearly a quarter of its territory, while Russia sought to complete its conquest of four additional provinces, in addition to Crimea, and demanded international recognition of its purported annexation. It also wanted Ukraine to become a neutral state.

The only way to end the conflict was for the US to devise a settlement that imposed equal sacrifices on both sides and used American power to force them to accept it. The plan involved offering a realistic and balanced peace settlement, threatening whichever side did not accept it with major negative consequences.

From Key Ukrainian Ally to Neutral Mediator

The first step occurred when Trump started to engage with Russia at the beginning of his administration. Having provided crucial military and intelligence aid to Ukraine during the Biden years, Kellogg insisted that the US needed to act as an “objective interlocutor.” However, Trump gave in when Russia rejected Kellogg as the principal mediator due to his argument in favor of strong punishment for those refusing to play the US game. Instead, he was relegated to managing relations with Ukraine, with Steve Witkoff emerging as the principal negotiator.

Initial signs were positive on the Russian side, with a long telephone call between Trump and Vladimir Putin in February considered “highly productive.” This led to fears among Ukraine and European allies that a rapid deal would be concocted, leaving out Ukraine. However, a meeting with a senior Russian delegation suggested that Moscow would not easily depart from its maximalist position.

Cutting Zelensky Down to Size

In response to such situations, mediators typically wait for things to change or, if they are powerful enough, effect the necessary change themselves. This seemed possible in the case of Ukraine. The second step was to bring Ukraine into line. The calamity in the Oval Office of February occurred when Zelensky failed to follow the script US officials had practiced with him, instead challenging Trump by arguing in favor of US security guarantees as the price for signing the controversial minerals agreement and acceptance of a ceasefire.

The US tried to persuade Zelensky that the deal would give the US a long-term strategic interest in Ukraine’s survival. However, while willing to sign, Zelensky went off script, seeing the initial welcome meeting as an opportunity to raise his key argument in favor of actual, hard military security guarantees for Ukraine.

Good Cop – Bad Cop

The UK played a role as the good cop, offering political and military support to Ukraine while assuaging the giant in the White House. Meanwhile, the US assumed the role of bad cop, forcing its terms upon Zelensky. After setting Ukraine on the path to a possible agreement, the question remained how to turn Russia.

The US correctly calculated that Putin would be much more difficult to press into concessions. Sanctions had not made much of an impression, given the fact that only the West was participating. Hence, Trump continued in his attempts to draw the Kremlin in rather than threatening him, offering the prospect of global rehabilitation, removal of sanctions, and deepened economic cooperation.

Creating the Decisive Moment

It was at this point that the US attempted to generate a decisive moment in the negotiations. Engineering such a point of decision is meant to force a recalcitrant side to opt either for more constructive engagement towards peace or to be blamed for the breakdown in the peace process and face further international sanctions.

The US response was daring, issuing a set of principles that could fit onto the back of an envelope. These principles included de facto but not de jure acceptance of Russia’s conquest, with the US alone defying international law to offer de jure recognition to the incorporation of Crimea. Sanctions against Russia would be progressively lifted, replaced with enhanced economic cooperation with the US.

However, the game was spoilt by Ukraine, which sent Trump a version of his principles that was modified in a few key points. This allowed Putin to evade the moment of decision constructed by the White House, leading to talks in Istanbul that yielded no results beyond some welcome prisoner exchanges.

Change of Heart in Washington?

Despite the setbacks, the US has achieved more than is evident at first sight. There now exists a blueprint in miniature, demonstrating that a settlement could be possible. While Ukraine is reserving its position in its direct discussions with Moscow, it now seems likely that Ukraine would in the end accept a deal based on the US “final” proposal, even if unenthusiastically.

The European partners have now understood that they would be principally left to address the issues of security guarantees for Ukraine on their own, with only limited US involvement. They have started to engage in real planning accordingly, whether it is for sustaining Ukraine in the war, for supporting a cease-fire, or assuring Ukrainian security after a settlement.

Conclusion

The US has gone very far in placing itself as a more “objective interlocutor” vis-à-vis Russia. While the calculation that Putin is unlikely to buckle to the kind of pressure the West can muster may not have been realistic, it was worth the try given the absence of viable alternatives. Washington has now given the Kremlin ample opportunity to exhibit interest in a settlement, and Putin has pretty much exhausted his repertoire of maneuvers to avoid engaging seriously.

It is now undeniable that Ukraine, the victim of aggression, is willing to settle, while Russia, the aggressor, is still banking on unqualified victory. This clear outcome opens the way for the application of yet greater pressure against Moscow, also for the previously reluctant White House.

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