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Zelenskyy’s Trump dilemma: Fight back or fold?

By staffOctober 13, 20264 Mins Read
Zelenskyy’s Trump dilemma: Fight back or fold?
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Volodymyr Zelenskyy has a right to be angry. 

In a wretched month for Ukrainians, ahead of a fast-approaching frigid winter, Donald Trump’s “very big and important deal” to acquire millions of tons of diesel fuel from Russia couldn’t have come at a worse time.

The U.S. president’s plan to lift sanctions on Moscow to allow diesel imports came as a sucker punch for most Ukrainians enduring barrages of jet-powered drones and ballistic missiles, with civilian casualties mounting.

The question for Zelenskyy is just how angry he can actually afford to be.

“His showing his frustration is understandable, but there are downsides,” said Tim Willasey-Wilsey, a former British diplomat and fellow at the Royal United Services Institute. 

The Ukrainian president immediately dubbed Trump’s deal a “weak decision” and “a gift to Putin” that will fund Russia’s war. Even more defiantly, he approved further drone strikes on Russian refineries, prompting Trump to call for Ukrainians to replace Zelenskyy as their leader.

Zelenskyy shows no signs of heeding Trump’s command to “better damn well stop” striking at Russia’s energy industry. That’s very much a continuation of his loss of patience this year, which has seen him sharpening his rhetoric toward both critics and allies, rebuking European leaders for moving too slowly with support, trading barbs with Hungary’s Viktor Orbán, and openly questioning Trump’s approach to the war. 

The tougher tone reflects mounting exasperation in Kyiv — especially with the U.S. president. Ukraine’s defense resilience and innovations with drones and missiles have augmented Zelenskyy’s confidence and readiness to push back. And yet, venting his frustration is not without risks.

Willasey-Wilsey suspects Zelenskyy may be calculating that Trump could emerge weakened from next month’s midterms, especially as some Republicans are already breaking ranks over the diesel deal. But the Ukrainian leader risks provoking Trump into cutting off vital U.S. intelligence support or pressuring Elon Musk to disable SpaceX’s Starlink internet service, on which Ukraine’s military heavily relies. 

Zelenskyy may be underestimating “how dangerous a wounded Trump could be” for Ukraine, warned Willasey-Wilsey.

The Trump administration has also threatened to halt a program through which allies purchase U.S. weapons for Ukraine, the Financial Times reported Monday. That would cause a major upheaval in supplies and force Kyiv to rely even more on its European allies, who are already struggling to rearm.

But Zelenskyy is standing firm. He insists Ukraine will only halt strikes on Russian oil refineries if Moscow ceases its air barrage. “Any de-escalation steps must be mutual,” he wrote on Telegram.

He has backing from an unlikely quarter: opposition lawmakers who are usually fierce critics of his leadership.

Even former President Petro Poroshenko, a bitter political rival, defended Zelenskyy against Trump’s call for his replacement.

“If anyone needs a new leader, it is Russia,” Poroshenko said in comments. “For me, the key question is simple: Are we any closer to a full and unconditional ceasefire? That is the only lens through which any move should be assessed.” 

Trump’s calls to replace Zelenskyy ironically strengthen the Ukrainian leader’s position at home, opposition lawmaker Mykola Knyazhitskiy said.

“There’s no greater campaigner for Zelenskyy than Donald Trump,” he added. “After every such conflict, Zelenskyy’s approval rating rises both in Ukraine and among our allies, particularly in Europe.” 

But Trump’s ability to force Kyiv into a settlement has diminished, according to Nathalie Tocci, who advised two former EU foreign policy chiefs. Having already withdrawn most American support, Trump has reduced his leverage over Ukraine and Europe, she argues. He could still inflict considerable damage by suspending intelligence sharing, but she doubts he would do so indefinitely or halt weapons sales. “If money is involved, I can’t see him pulling the plug on sales,” she said.

But the fear in Kyiv is that Trump’s pursuit of a deal with Moscow will come at Ukraine’s expense.

Ivanna Klympush-Tsintsadze, a prominent opposition lawmaker and former deputy prime minister, sees little prospect of Putin compromising. “He’s not ready to stop the war or even agree a ceasefire,” she said.

“From my understanding, all the other ‘deals’ which have supposedly been discussed by U.S. negotiators with the Russians have been only about the capitulation of Ukraine and basically the country ceasing to exist as a free, independent, sovereign state.”

That likely explains Zelenskyy’s open anger. He knows that antagonizing Trump comes at a price. But so does appeasing a U.S. president who seems increasingly willing to do business with Putin. For Ukraine, neither option is good. 

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