When Donald Trump and Vladimir Putin meet in Alaska this Friday, the headlines will focus on the show: a US president hosting the Russian leader in a state once sold by the Russian Empire, with Ukraine’s fate hanging in the balance. But what’s invisible to many is a fundamental problem. The two men are not even negotiating the same war.

Trump and his advisers frame the war as a territorial dispute.

In Trump’s mind, ending the war is a matter of finding the right chunk of land to trade, a deal that can be signed quickly, sold to voters, and wrapped up before the next election cycle.

Putin’s view is entirely different. For him, this war is not about lines on a map. It is about the structure of Europe’s security order. His core demand, repeated for more than a decade, is a legally binding halt to NATO expansion, not just for Ukraine, but as a principle. That means rewriting the post–Cold War rules so that Moscow has a permanent veto over the alliances its neighbors may join.

But Putin’s demands go far beyond strategic reordering. According to Russian officials, Moscow seeks Ukraine’s complete “demilitarization,” “denazification”—Putin’s euphemism for regime change—and permanent “neutrality” barring any Western security guarantees.

Russia also wants all sanctions lifted and NATO forces rolled back from Eastern Europe entirely.

In other words, Putin is not negotiating over Ukrainian territory. He is negotiating over whether Ukraine will continue to exist as an independent state.

• Trump is playing a game of Monopoly;
• Putin is erasing countries from the map.

What Ukraine cannot accept

This fundamental mismatch leaves Ukraine in an impossible position. Trump is willing to trade away frozen conflict lines, delayed NATO membership, and limited sanctions relief. But Ukraine needs what Putin refuses to give: genuine security guarantees, territorial integrity, and the sovereign right to choose its own alliances.

These are not positions Ukraine can compromise on—they are requirements for survival as an independent nation. Yet they are precisely what Trump’s deal-making approach treats as negotiable.

History’s warnings

There is no shortage of historical warnings about what happens when talks are built on such mismatches. Land swaps have been tried before as a way to paper over deeper disputes.

• Kosovo and Serbia explored trading territory to normalize relations; it collapsed under nationalist backlash.
• Serbia and Croatia’s postwar boundary negotiations left core tensions untouched, producing only fragile arrangements.
• Estonia and Russia agreed to a border treaty in 2005; Moscow withdrew when Estonia joined NATO.

In each case, the failure came from mistaking a strategic conflict for a cartographic one.

Negotiating with shadows

There is a deeper risk that analysts have largely overlooked: Trump is negotiating with his own misunderstanding of Putin’s objectives. Because he believes the dispute can be solved by trading territory, he will interpret any territorial discussion as progress.

Putin, meanwhile, will see territorial concessions only as a means to secure the larger prize of a rewritten security order.

This misunderstanding becomes Putin’s greatest asset. Russian analysts describe Trump’s dealmaking approach as a “can’t-lose proposition” for Moscow. Putin can appear reasonable and open to compromise while presenting terms designed to eliminate Ukrainian independence.

Even if Trump rejects specific demands, Putin achieves his goal of being treated as Ukraine’s equal in determining the country’s future.

Trump and Putin will leave Alaska believing they have moved closer to a deal, but they will be moving along two separate tracks that never meet.

• Trump will think he has made progress toward a territorial settlement;
• Putin will have advanced his goal of erasing Ukraine as a sovereign state.

Asymmetry in preparation

If this were merely a matter of clashing goals, careful preparation could at least surface the differences and test for overlap. But here too, the asymmetry is visible. Putin arrives in Alaska with a tightly controlled plan, informed by months of private discussions with his closest advisers, and with clear red lines. Trump arrives without a detailed framework.

Successful summits rarely happen spontaneously.

• Camp David in 1978 followed 13 days of intense, private negotiation and years of backchannel talks.
• The 1986 Reykjavik meeting between Reagan and Gorbachev, itself considered a failure at the time, was built on months of arms control groundwork.

Alaska has none of this. The meeting was triggered by a visit from Steve Witkoff, a real estate developer turned envoy, who came back from Moscow with little more than a handshake agreement to meet.

That imbalance gives Putin the advantage. He can use the summit to appear open and constructive while presenting terms designed to lock in strategic gains.

Even if Trump refuses those terms, Putin will have succeeded in demonstrating to his domestic audience, and to wavering countries in the Global South, that Russia is negotiating directly with Washington, sidelining Kyiv.

A timeline mismatch

Time itself favors Putin. Trump is thinking in months, hoping for a quick foreign policy win before the 2026 midterms.

Putin thinks in decades. His inner circle, according to Russian sources, has told him that Ukrainian resistance will collapse within months if Russia maintains military pressure.

• For Putin, a pause is not a compromise. It is a tactical stage in a longer campaign.
• For Trump, a pause can be sold as peace.

This is why a meeting that produces no concrete concessions from Moscow can still be useful to both men, but deeply damaging to Ukraine.

The symbolism problem

Then there is Alaska itself. Meeting on American soil might seem like a show of strength from Trump, but to Putin, it means something else. Alaska was once Russian territory. Hosting the summit there sends an unintended message: that borders are temporary and land can be transferred through negotiation. In a war where Russia’s central claim is that borders can be rewritten by force, this is a gift.

Diplomats understand the power of location. In 2010, Serbia and Kosovo’s EU-sponsored talks were held in Brussels precisely to avoid symbolic claims to sovereignty. Choosing Alaska to discuss Ukraine’s future undermines the very principle the US claims to defend: that states have the right to keep their internationally recognized borders.

The real danger of Alaska is not that it produces a signed surrender. The danger is that it produces the illusion of progress.

Trump could emerge declaring the talks a first step toward peace, while Putin uses the meeting to reinforce his narrative: that Washington, not Kyiv, is the true counterparty in this war, and that Russia’s demands are the baseline for any serious negotiation.

What success would require

Could Alaska succeed? Only if both leaders arrived with a shared understanding of the core dispute, a set of pre-negotiated principles, and Ukraine’s active participation.

None of those conditions exist.

Without them, the meeting is not a step toward resolution but a set piece in two domestic political dramas: Trump’s need to appear as the great dealmaker, and Putin’s need to appear as the indispensable architect of Europe’s future.

But the stakes are higher than political theater. Trump’s misunderstanding could lead him to pressure Ukraine into accepting a “peace” that eliminates its independence while allowing Putin to claim he negotiated rather than conquered.

That is why the Alaska summit may be remembered not as a turning point toward peace, but as the moment when the West negotiated away a democracy’s right to exist.