Trump-Putin meeting in Alaska: What’s at stake and why it matters

During his first term, Trump’s meetings with Putin were closely watched by senior advisers like John Bolton, Mike Pompeo, and Jim Mattis—officials known for their scepticism of Moscow. Today, Secretary of State Marco Rubio is the only senior figure in Trump’s circle with a record of challenging Putin, but his tone has softened since joining the administration. This has raised concerns that Trump has fewer internal checks against agreeing to terms favourable to Russia.

The role of Trump’s envoy

The Alaska meeting follows a visit to Moscow by Trump’s special envoy, Steve Witkoff, a real estate associate with no prior diplomatic experience. Witkoff has been criticized for meeting Putin without other US officials present and for echoing Kremlin talking points afterward. His appointment has fuelled criticism that Trump is relying on personal channels rather than structured diplomacy.

Past patterns and low expectations

Analysts point out that Trump’s history with authoritarian leaders—from Xi Jinping to Kim Jong-un—has yielded few lasting deals. In his first term, private conversations with Putin were sometimes conducted without US note-takers, and Trump occasionally adopted Russian talking points after their meetings. Experts like Fiona Hill and Maria Snegovaya say there is little reason to expect a breakthrough on Ukraine now, given Putin’s battlefield calculus and Trump’s informal style.

Risks for US policy

For Putin, the Alaska meeting is a chance to regain influence over Trump’s thinking on Ukraine. For Trump, it’s an opportunity to showcase a hands-on approach to ending the war. But without a structured negotiation framework, any outcome may be more symbolic than substantive—and critics worry it could erode the unified front that has so far kept US policy aligned with its allies in supporting Kyiv.