Big moments in Trump’s negotiations: From a shouting match with Zelensky to threats of sanctions against Russia

Big moments in Trump’s negotiations

US President Donald Trump’s campaign pledge to end the Ukraine war on “Day One” of his second term has collided with the stubborn realities of diplomacy and the battlefield. As he prepares for a face-to-face meeting with Russian President Vladimir Putin at Joint Base Elmendorf-Richardson in Anchorage on Friday, the first such encounter of his new term, Trump faces growing pressure to show progress. The war has dragged on for more than three years, and both Ukrainian and European leaders remain wary that the US president might make concessions without their involvement, CNN reported.

Trump’s return to direct talks with Putin follows months of high-profile but unsuccessful diplomacy. In February, his public meeting with Ukrainian President Volodymyr Zelensky erupted into a heated confrontation, with the two leaders openly clashing over possible territorial concessions. Trump has since spoken by phone with both Putin and Zelensky multiple times, each call underscoring the gulf between their positions. Despite his often-repeated claim of a “very good relationship” with Putin, Trump has struggled to translate personal rapport into tangible results.

Frustration behind the scenes

The White House has acknowledged that Putin has shown little inclination toward compromise. US officials say that while Trump has alternated between praising the Russian leader and sharply criticizing him — at one point calling him “absolutely CRAZY” — the Kremlin has remained entrenched in its demands. Attempts to apply pressure have included the threat of new sanctions, but none have yet been imposed.

Trump has also relied on his envoys, dispatching them to European capitals to gauge support for various ceasefire frameworks. The missions have met with mixed results, with NATO allies privately expressing concerns that Trump’s approach might bypass Ukraine’s core interests. Zelensky has been particularly vocal, warning against any agreement that would cede Ukrainian territory, especially the contested Donbas region, to Russian control.

White House lowers expectations

In the days leading up to the Alaska meeting, administration officials have worked to temper public expectations. While Trump insists he is committed to pursuing peace, aides have stressed that the US cannot dictate the terms of an agreement and that the outcome depends largely on the willingness of Moscow and Kyiv to compromise. This more measured tone marks a departure from Trump’s early declarations that he alone could “get it done” quickly.

Still, the decision to meet Putin now is being framed as part of a more aggressive pressure campaign. Trump, increasingly frustrated with the lack of movement, is said to believe that direct engagement is the best way to force a breakthrough. The meeting’s location — on US soil but far from Washington — is seen by some observers as a symbolic gesture, projecting both openness to dialogue and control over the setting.

Risks and opportunities

Analysts say the stakes are high. A successful meeting that lays the groundwork for a ceasefire could strengthen Trump’s standing internationally and vindicate his personal diplomacy strategy. But a failure to achieve progress could embolden Putin, signalling that the US lacks the leverage or will to alter the course of the war.

Some foreign policy experts worry that the summit could tilt in Moscow’s favour if Trump is not prepared to match firm rhetoric with concrete actions. Without prior alignment with European allies and Ukraine, there is also the risk of deepening divisions within the Western coalition.

The road ahead

Whether the Alaska summit becomes a turning point or another missed opportunity will depend on what happens behind closed doors. Trump has hinted that he will push Putin harder than before, but it remains unclear whether that will include immediate punitive measures or a timeline for renewed sanctions. For now, the focus will be on whether Trump can move beyond what has so far been a cycle of tense conversations, unmet threats, and stalled negotiations.

As one senior US official put it this week, “The president knows this is not just about one meeting. It’s about whether we can create a path forward. But if Putin is not ready to deal, there’s only so much anyone can do.”

With both leaders heading into Friday’s talks from entrenched positions, the Alaska meeting could be remembered either as the moment Trump began to make real progress — or as the latest chapter in a series of failed efforts to end one of the most intractable conflicts of his presidency.