Trump Seeks Breakthrough in Russia-Ukraine War with High-Stakes Calls to Putin and Zelenskyy

In a bold diplomatic move, former U.S. President Donald Trump is scheduled to hold separate calls on Monday with Russian President Vladimir Putin and Ukrainian President Volodymyr Zelenskyy, hoping to advance discussions toward a ceasefire in the ongoing conflict between the two nations.

Trump previewed his initiative in a weekend post on Truth Social, expressing hope for a “productive day” that could edge the war closer to a pause. The outreach includes planned conversations with NATO allies as Trump looks to leverage his personal rapport with global leaders in pursuit of peace.

According to Kremlin spokesperson Dmitry Peskov, the Trump-Putin call is scheduled for 5 p.m. Moscow time (10 a.m. Eastern), and will follow up on recent diplomatic talks in Istanbul—the first face-to-face negotiations between Russian and Ukrainian officials since 2022.

A High-Stakes Test of Trump’s Deal-Making Credentials

Trump has long claimed he could swiftly end the Russia-Ukraine war, positioning his diplomatic skills as a key asset. Monday’s calls now serve as a crucial test of that promise. His allies say the former president is relying on his longstanding relationship with Putin to break the deadlock.

“Trump believes his direct conversation with President Putin will help cut through the stalemate,” said Steve Witkoff, a key envoy. “He’s confident it’ll be a meaningful exchange.”

Yet critics worry Trump’s perceived affinity for Putin may skew negotiations in Russia’s favor. Former U.S. Ambassador to Ukraine Bridget Brink, who resigned last month, criticized the administration’s approach, claiming it pressured Ukraine more than Russia.

“I resigned because I couldn’t support a policy that coddles the aggressor while sidelining the victim,” Brink said, recalling a February Oval Office meeting where Zelenskyy was reportedly scolded for lacking deference.

Economic Leverage and Diplomatic Stakes

Trump has indicated that Monday’s conversation with Putin will also touch on trade—hinting that he may use economic incentives to influence negotiations. He described the war as a “bloodbath” that “should have never happened” and hinted at leveraging sanctions and trade deals as bargaining chips.

Treasury Secretary Scott Bessent echoed that approach on NBC’s Meet the Press, stating that failure by Russia to engage in “good faith” could prompt tougher sanctions. Bessent also argued that earlier measures under President Biden failed to curb Russia’s oil profits, which continue to fuel the war effort.

Prisoner Swap Proceeds as Ceasefire Hopes Dim

Although hopes for a ceasefire remain elusive, progress has been made on humanitarian fronts. Following short-lived peace talks in Turkey, both Russia and Ukraine have agreed to a mutual exchange of 1,000 prisoners of war. Ukraine’s intelligence chief Kyrylo Budanov suggested the transfer could happen within days.

Meanwhile, Trump, returning from a Middle East visit, blamed Putin’s absence from Turkey on his own non-attendance. “He and I will meet, and either we’ll solve this or we won’t—but at least we’ll know,” Trump told reporters.

Zelenskyy, who spent Sunday meeting with Vice President JD Vance and Secretary of State Marco Rubio in Rome, reaffirmed Ukraine’s commitment to “real diplomacy.” In a post on X, he criticized the Russian delegation at the Istanbul talks as lacking decision-making authority and emphasized the need for continued pressure on Moscow.

Global Support Builds for Ceasefire Push

Ahead of Monday’s high-stakes calls, Trump also spoke with German Chancellor Friedrich Merz and leaders from France, the UK, and Italy. French President Emmanuel Macron later posted on X, urging Putin to accept the proposed 30-day ceasefire as a “first step toward peace.”

However, the Kremlin's military actions continue unabated. Over the weekend, Russia launched its largest drone assault since the war began, deploying 273 explosive drones and decoys across Ukraine, targeting Kyiv, Dnipropetrovsk, and Donetsk.

As anticipation builds around Monday’s calls, Trump faces mounting pressure to deliver on his promises of peace. Whether his direct diplomacy will yield results remains to be seen—but the world will be watching.