Trump says Alaska meet with Putin has 25% chance of failing

Trump warns Putin to move toward peace in Ukraine or face action Credit: GettyImages

Alaska meeting carries high hopes and hard limits, with Donald Trump openly saying it could stumble while hinting at a bigger plan to follow. Donald Trump has cast the Alaska session with Vladimir Putin as a “feel-out” meeting, saying there’s a 25% chance it could fail and framing it as groundwork for a larger, three-way summit with Ukraine’s Volodymyr Zelensky to discuss land and borders.

The Kremlin has warned against expecting major outcomes, suggesting the first encounter is meant to prepare future steps rather than deliver immediate decisions. Plans call for a one-on-one format with interpreters, reinforcing the notion that this round is limited in scope and designed to test intentions.

Trump likened the approach to “chess,” saying he intends to quickly judge Putin’s readiness to deal and, if satisfied, invite Zelensky to a second meeting focused on concrete arrangements. However, Russian aides have signaled skepticism about moving to a trilateral format so soon, tempering talk of a quick three-way summit.

Trump has also warned of “severe consequences” if Putin does not change course, underscoring that any follow-up gathering hinges on how the Alaska talks unfold.

Zelensky has repeated that Ukraine’s constitution bars ceding territory, insisting Ukrainians will not give land to the occupier and rejecting any territorial swaps. Kyiv argues that conceding regions such as Donbas or others would embolden future Russian aggression, making such a path unacceptable.

The landscape is further complicated by Russia’s annexation of Crimea in 2014 and its 2022 claims over four additional regions, which collide with Ukraine’s legal stance and make any land-based arrangement fraught.

Trump says the follow-on meeting would be the venue for an actual deal, but he has also suggested there may be no second session if Alaska does not yield the answers he needs. The Kremlin has downplayed the likelihood of a quick trilateral, even as European concerns linger over any settlement made without Ukraine present; Trump has maintained he will not finalize terms with Putin alone. Meanwhile, Moscow projects caution about outcomes while seeking recognition of battlefield gains, and Kyiv rejects any deal that legitimizes occupation.

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Economic and geopolitical pressure looms over the talks. U.S. officials have warned that secondary tariffs on India could rise if the Alaska meeting collapses, signaling that Washington is tying outcomes to broader sanctions and trade leverage.

Recent measures include a 25% penalty on Indian imports plus an additional 25% on purchases of Russian oil and weapons, with potential increases if diplomacy falters. This warning adds another layer of stakes, even as the war’s shifting front lines heighten urgency and harden positions.

Trump’s message is clear: the Alaska summit is a preliminary move with a declared risk of failure, intended to set up a higher-stakes trilateral where boundaries could be debated—if all sides agree to attend.

Ukraine’s categorical refusal to surrender land, Russia’s entrenched claims since 2014 and 2022, and the Kremlin’s caution on expectations mean even a second meeting would run into rigid legal, political, and military realities.