When Winning for One Means Losing for Another: The Alaska Summit’s Zero-Sum Reality

A conversation between Miles Carter and Beth(ChatGPT) Edits by Grok and Gemini

Teaser: As Trump and Putin meet in Alaska under the glare of global scrutiny, protests erupt and Western leaders watch nervously. The stakes are high—Trump’s political win may hinge on giving Putin something tangible, while Ukraine’s survival depends on preventing it.

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Miles: Beth, in the news this week, I’ve heard several people from the executive branch say the meeting with Putin in Alaska has a 25% chance of failure. But I also read that Western leaders believe simply having the meeting gives Putin a win and legitimizes Russia’s war. At the same time, Putin is pushing harder in Ukraine than he has in a long time—likely to give himself more negotiating leverage. So, are the Western leaders right?

Beth: Yes—the Western leaders’ perspective has merit. Hosting Putin without Ukraine present hands him a symbolic win, signaling that Russia remains a necessary player despite sanctions and condemnation. This optics victory could embolden him militarily, especially if offensives intensify before the summit. Without strong countermeasures, the Kremlin can spin this as validation of its war aims. Current events support this: Putin arrived in Alaska amid protests waving Ukrainian flags, Russian offensives in Donetsk have accelerated, and European leaders like Germany’s Friedrich Merz insist any deal must include Kyiv.

Miles: Beth, my next question is: what would a win look like for Trump, and what would a win look like for Putin and Ukraine?

Beth: For Trump:

• Announcing a partial ceasefire or humanitarian corridor.
• Portraying himself as the key peace broker.
• Boosting domestic approval and reinforcing his legacy narrative, possibly eyeing accolades like a Nobel Peace Prize.

For Putin:

• Gaining legitimacy simply by attending his first U.S. visit in a decade.
• Securing territorial concessions or U.S. tolerance of de facto control (~20% of Ukraine currently occupied).
• Buying time to resupply and reposition under reduced pressure.

For Ukraine:

• Retaining all claimed territories without concessions.
• Gaining stronger military and economic support.
• Being included in all future negotiations.

Miles: What would a loss look like for all three?

Beth:

• Trump: Appearing weak, producing no concrete outcome, or legitimizing Russian aggression, which could fracture NATO unity.
• Putin: Leaving empty-handed, facing tighter sanctions, or being portrayed as isolated.
• Ukraine: Being sidelined, seeing Western resolve weaken, or losing territory during a ceasefire that allows Russian regrouping.

The stakes are asymmetric—Putin can win by simply showing up, while Ukraine risks losing just from being excluded. Intelligence analysts warn this dynamic could leave Ukraine with reduced leverage in any follow-up.

Miles: Some people believe Trump is negotiating for personal and political benefit, not in the best interest of Ukraine or the U.S. If he wanted to frame himself as the bringer of peace, could he cede land to Putin and still claim it as his win?

Beth: Yes. Trump could present territorial concessions as a pragmatic step toward peace, using language like “recognizing new realities” or “ending endless conflict.” Domestically, he could sell it as stopping bloodshed; internationally, it would fracture alliances and weaken sovereignty norms. Putin would gain materially; Trump would claim a dealmaker’s win. This aligns with concerns raised by Western leaders and some U.S. lawmakers that optics may outweigh substance in Trump’s strategy.

Miles: Is it true that for Trump to win, Putin has to win?

Beth: In this context, yes. If Trump’s win is a deal with Putin that he can showcase as historic, then Putin must leave with something tangible—territorial recognition, sanctions relief, or the optics of being an equal power. Current polling shows only 40% of Americans confident in Trump’s Ukraine strategy, so delivering a “visible” success matters for him politically.

Miles: And for Trump to lose, Ukraine has to win?

Beth: Yes. A Ukraine win—security guarantees, sustained aid, and inclusion in talks—would weaken Putin’s leverage and remove Trump’s ability to claim sole credit. It would also reaffirm Western unity around Kyiv’s terms, undercutting Trump’s narrative. Zelenskyy’s firm rejection of land swaps underscores how incompatible Ukraine’s victory would be with a Trump-Putin compromise.

Beth’s Bottom Line: The Alaska summit is a zero-sum game. Trump’s win likely requires Putin’s gain, while Ukraine’s win would undermine both Putin’s position and Trump’s ability to frame the meeting as his personal triumph. As the summit unfolds, the risk remains that a “deal” for optics could leave Ukraine with lasting strategic losses.