Trump-Putin Alaska Summit Preview, Paid Subscriber Debrief

AMA at 6:30pm ET on Substack Live

Dear readers,

Today is the highly anticipated Trump-Putin summit in Alaska. This meeting may have huge implications for American geostrategy and could fundamentally alter the course of the ongoing Russia-Ukraine war. I wanted to provide my perspective on the potential outcomes of this meeting and what it means for the United States, Ukraine, and the world as a whole. You’ll notice that it’s similar to my statement from yesterday with some timely updates - I stand by my initial assessment and believe that this administration is fundamentally unprepared for today’s summit.

However, I also wanted to announce that after the summit I will be holding a special paid-subscriber only debriefing at 6:30pm ET, where you can ask me anything about the Trump-Putin summit. You can ask a question in the 08/15 thread on the Substack chat app linked here. I’d love to hear what you have to think and I hope you can join me later tonight.

The United States has no concrete plan for today’s summit between Donald Trump and Vladimir Putin. This is more than just an oversight by an administration known for its lack of long-term policy planning: this is an invitation for trouble. Bilateral summits between major powers require months of behind-the-scenes preparation and extensive alignment between relevant parties. If done correctly, this ensures that heads of state are finalizing a deal and not improvising a new agreement (or alternatively, both parties realize they cannot move beyond an impasse and walk-back the potential summit).

Given the rapid oscillations in Trump’s Russia policy over the past six months, there’s no reason to believe that this summit was organized well in advance - I would go as far as to say that the Trump team began planning the summit shortly before it was announced to the public following the expiration of Trump’s “deadline”. The lack of preparation shows: there’s no mutual agreement on a ceasefire, no alignment on whether or not Ukraine will be expected to surrender territory, and no agreement on any sort of post-war peacekeeping, monitoring, or security guarantees. Ukraine isn’t even invited to the summit. It’s looking like today the president will walk into a room and rely purely on his instincts in negotiating against a counterpart who has built a career exploiting exactly these kinds of open-ended encounters. By Trump’s own admission, this negotiation has a 25% chance of failure. I’m sure a former KGB operative like Putin loves the prospect of a 1:1 negotiation with someone that’s willing to win a Nobel Peace Prize at all costs, even if it means Ukrainian surrender.

Leaving the meeting’s substance undefined creates a vacuum that Putin will be eager to fill. History has shown how dangerous this approach can be. Successful summits from Reykjavik to Camp David to Dayton required rigorous diplomatic groundwork beforehand that narrowed disagreements and set clear expectations. Without that foundation, the outcome of the summit becomes a matter of who is better prepared to seize the initiative and direct the conversation. In this area, the advantage lies firmly with Moscow.

The stakes go well beyond Ukraine’s borders. By excluding Ukraine and the EU, Trump is treating Russia as the only actor with agency in the negotiation process and is giving Moscow unparalleled decision making ability with regards to European security. Recent details published over the past two days include reports that the Trump administration is looking to easing sanctions on the Russian Federation as part of the negotiation process. One proposal includes extending mining rights to Russian firms for operations in Alaska or occupied Eastern Ukraine. Beyond the immediate questions regarding the legality of these offers (and Trump’s ability to extend them due to congressional oversight), offers of economic relief may splinter the united front between the United States and European Union on the topic of sanctions against Russia. Moreover, it appears that these concessions are being offered without the inclusion of a ceasefire or freezing of the conflict line. All these signs point to a lack of coordination and a frantic, last-minute effort to cobble together a peace platform that’s bound to fail.

One possible outcome is that Trump agrees to terms heavily skewed toward Russia, including territorial concessions by Ukraine, acceptance of Moscow’s expanded sphere of influence, or reduced military support for Kyiv. These offers would only embolden the Kremlin’s appetite for further expansion and plunge Europe into an even greater state of alert. While Ukraine would keep fighting, the lack of American military aid would have an immediate impact on Ukraine’s ability to fight and defend its civilian population against the Russian military.

Another possibility is that the meeting ends without an agreement. The fighting in Ukraine grinds on, only now Washington is further estranged from its European allies having organized the summit and potential peace terms without their consultation. The absence of a united front would make joint military planning more difficult, erode interoperability, and weaken the Western alliance’s ability to deter future aggression. Moreover, our allies abroad will spend the remainder of Trump’s presidency wondering if the United States will leave them in the dark and negotiate on their behalf in response to potential great power competition.

The third scenario is that of the “optics win,” a shallow compromise that allows Trump to claim victory at home while granting Putin enough leeway to keep his long-term objectives intact. This outcome would be seen by every authoritarian leader as proof that the United States can be maneuvered into trading away strategic leverage for a press release and photo op of a smiling Trump holding up signed paper. This would outright alienate Washington from its allies and send the message that the United States is fundamentally uninterested in upholding its principles and defending the post-war order.

The least likely scenario is Trump walking away empty hand, not looking the part of a deal maker. In this scenario, would throw his hands in the air, lose interest in ending the Russia-Ukraine war and move to easier PR wins. Or less likely, he could levy harsh sanctions on Russia and energize support for Ukraine to pressure Putin into negotiations and peace.

In all three cases, the effect is the same: American deterrence is weakened, Russia’s revanchism is encouraged, and the risk of new, greater security challenges in Europe is increased. Undermining our credibility in such a way in the midst of rising tensions with China, Iran, and Russia is like scattering gunpowder on the floor and daring someone to strike a match.

Putin opened with a demand that Ukraine withdraw from territories that the Russian military has failed to capture. This shows his confidence in shaping the agenda and his strategic interests in the negotiation process. The Russian government’s lack of commitment towards a concrete ceasefire suggests a familiar pattern seen in early negotiations: secure concrete gains in exchange for vague promises, then use those gains as a platform for the next push. Without firm conditions, the United States will play directly into Russia’s strategy.

For Ukraine, national survival depends on more than simply an end to the shooting: it requires binding, credible security guarantees that deter future attacks. For Zelenskyy, the acceptance of an agreement that has no means of providing a durable, lasting peace means accepting defeat today and war in the future. The only acceptable outcome from a U.S. perspective is one that leaves Ukraine’s sovereignty intact, integrates it firmly with the West, and provides enforceable protections against renewed Russian aggression. That is not the trajectory this summit is on. By going in without any substantial preparatory work, Trump has set the stage for disaster.