Timeline of Tensions Between Trump and Zelenskyy

Former President Donald Trump has criticized U.S. military support for Ukraine and has expressed discontent with Ukrainian President Volodymyr Zelenskyy since his first term. Recently, Trump called for Zelenskyy's removal, attributing rising diesel prices to the Ukrainian leader's actions, which he claims have impacted the Republican Party ahead of the November midterm elections. This criticism coincides with heightened tensions following Trump's announcement of a diesel supply deal with Russia. "I think it’s time for Ukraine to get a new president," Trump stated, alleging that Zelenskyy has harmed global diesel supplies by targeting Russian refineries. Zelenskyy responded by affirming his commitment to continue strikes on Russian oil refineries, stating, "Ukraine will be ready to stop striking Russian oil refineries if Russia stops striking our energy infrastructure." Their fraught relationship dates back to Trump's first term, when he pressured Zelenskyy to investigate his political rival, Joe Biden, and his son, Hunter Biden. A timeline of Trump's criticisms of Zelenskyy includes several key instances: In October 2026, Trump criticized Zelenskyy for failing to secure a peace deal and urged him to cease attacks on Russian energy facilities. Trump remarked, "He better damn well stop," suggesting that Ukraine should consider a new leader capable of negotiating. In April 2025, Trump implied that Ukraine had instigated the war against Russia and criticized Zelenskyy for his statements regarding Crimea, stating that such comments hinder peace negotiations. In a February 2025 Oval Office meeting, Trump and Vice President JD Vance confronted Zelenskyy over various issues, leading to a heated exchange. On February 19, 2025, Trump labeled Zelenskyy a "dictator without elections" and accused him of prolonging the conflict for U.S. support. During the 2024 campaign, Trump continued to criticize Zelenskyy for not making sufficient efforts to negotiate peace with Russia. In July 2019, Trump urged Zelenskyy to collaborate with Rudy Giuliani and the U.S. attorney general to investigate Biden, amidst the withholding of nearly $400 million in military aid to Ukraine. Zelenskyy later stated he did not feel pressured during their conversation.