The art of no deal in Alaska
Trump has enormous leverage with Putin – if he's willing to use it. Including walking away.
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And now…the Alaska summit
Can the self-proclaimed master of the deal outsmart a former KGB operative who has spent the better part of two decades studying how to manipulate American presidents?
That's the central question as Donald Trump prepares for his Friday summit with Vladimir Putin in Alaska.
Trump has never lacked faith in his own negotiating prowess. But after months of phone calls where Putin nodded politely and then proceeded to bomb Ukrainian nursing homes, even Trump's legendary self-confidence has been shaken by an uncomfortable realization: Putin isn’t necessarily the "friend" he once imagined.
But here's the thing about Trump that his critics consistently underestimate – when he realizes he's been played, he doesn't just get angry. He gets strategic. At least temporarily. And that shift in his thinking about Putin may be the most significant development heading into what could be the most consequential summit between the US and Russia since Yalta.
The historical echoes are unsettling. Here we have an American president preparing to meet with a Russian leader to negotiate the future of Eastern European territory, while the affected country – Ukraine – remains conspicuously absent from the table. It's a scenario that European leaders know all too well from their history books.
The parallels to the Yalta summit are impossible to ignore. In 1945, Roosevelt, Churchill, and Stalin carved up Europe into spheres of influence, deciding the fate of Poland and other Eastern European nations without inviting them to the table. The result was decades of Soviet domination that these countries are determined never to repeat.
But there's a crucial difference: Roosevelt and Churchill were negotiating with a brutal but necessary wartime ally. Trump is sitting across from the aggressor himself.
That distinction matters more than Trump's critics want to acknowledge. Putin isn't Stalin circa 1945 – a brutal but necessary partner in defeating Hitler. He's Hitler circa 1938, demanding territorial concessions from a sovereign democracy while threatening broader conquest if he doesn't get his way. The question is whether Trump recognizes the difference.
Recent evidence suggests he might. The president who once boasted about his "wonderful conversations" with Putin now openly admits that those chats are followed by Russian rockets hitting apartment buildings. That's not the language of someone still under Putin's spell – it's the frustration of a deal-maker who's slowly realizing his counterpart has been negotiating in bad faith.
Trump's growing irritation with Putin represents a fascinating evolution in his thinking about Russia. Where once he saw potential partnership, he now sees manipulation. Where once he imagined grand bargains, he now confronts the reality that Putin views any agreement as merely a pause between escalations.
This shift explains why European leaders, despite their public anxiety about Friday's summit, may have found their most receptive audience yet in Trump. Wednesday's virtual meeting wasn't just diplomatic theater – it was strategic coordination between partners who finally agree on the fundamental challenge they face.
The five principles that emerged from that call reveal a Trump administration that has moved considerably closer to European thinking: Ukraine must remain "at the table" for future negotiations, territorial discussions can only follow a ceasefire, security guarantees are non-negotiable, and economic pressure on Russia must increase if diplomacy fails. These aren't the talking points of someone preparing to cave to Putin's demands.
Of course, Trump has a well-established pattern: he'll pledge solidarity with European allies about standing firm against Russian aggression, only to emerge from his next Putin phone call singing a different tune, suddenly critical of Ukrainian "intransigence" and Zelensky's "unrealistic demands." The real test isn't what Trump promises going into Alaska – it's whether he can resist Putin's charm offensive and practiced manipulation once they're alone in a room together.
The European strategy of surrounding Trump with allies who can credibly claim to support his dealmaking while constraining his options is shrewd. But it also reveals the fundamental weakness of their position: they need American power to deter Russian aggression, but they can't control how that power gets used.
The stakes of Friday's meeting remain enormous for Trump precisely because his reputation as a deal-maker is on the line. This isn't just about Ukraine's future or Europe's security – it's about whether Trump can deliver one of the signature promises of his presidency: ending wars through personal diplomacy.
The irony is that Trump may find the strategic clarity to outmaneuver Putin at exactly the moment when Putin has the least incentive to make genuine concessions. Russian forces are advancing, sanctions are proving insufficient to change Moscow's calculus, and Putin likely believes time is on his side. Why settle for half of Ukraine today when you might get all of it tomorrow?
This dynamic creates a dangerous trap for Trump. If he emerges from Alaska empty-handed, he'll face pressure to either escalate confrontation with Russia or abandon Ukraine entirely. If he accepts a deal that rewards Russian aggression, he'll validate every European fear about American unreliability. And if he walks away claiming progress while Putin continues his assault, he'll look like exactly the kind of leader Putin has always taken him for – someone more interested in the appearance of success than its substance.
And that is what makes this moment genuinely perilous: Putin isn't just betting that he can manipulate Trump. He's betting that he can manipulate Trump's desire to be seen as a successful dealmaker. The Russian leader's entire strategy appears designed to offer Trump something that looks like victory while delivering everything Putin actually wants.
A ceasefire that freezes current lines? Putin gets to keep his territorial gains while rebuilding his forces. Economic partnerships with Russia? Putin breaks out of Western isolation while Trump claims credit for pragmatic engagement. A pledge to respect Ukrainian sovereignty while denying NATO membership? Putin gets a neutered neighbor while Trump declares peace in our time.
Trump actually does have leverage – enormous leverage – if he's willing to use it. Hundreds of billions in frozen Russian assets, secondary sanctions against that could cripple Russian energy sales, and a military aid pipeline that could tip the battlefield balance all sit within his power. The question is whether his eagerness for a deal will prevent him from wielding these tools effectively.
What Trump needs more than anything heading into Friday isn't just confidence in his dealmaking abilities – he needs a strategy that accepts the possibility of walking away. He's done it before, most notably abandoning his nuclear negotiations with North Korea's Kim Jong Un despite their much-vaunted "love letters" and personal chemistry. The question is whether his ego can survive doing the same with Putin, especially after months of promising a quick resolution to the Ukraine conflict.
The Alaska summit may indeed echo Yalta, but not necessarily in the way European leaders fear. Both meetings featured Western powers trying to constrain a Russian leader's imperial ambitions through personal diplomacy. The difference is that Roosevelt and Churchill had just won the largest war in human history and were negotiating from a position of strength. Trump is negotiating from a position of frustration, which may actually serve him better than anyone expects.
Because here's the thing about frustrated dealmakers: they're often more willing to walk away from bad deals than patient ones. And sometimes, the threat of no deal is the only thing that motivates the other side to offer a real one.
Friday will test whether Trump has learned that lesson, or whether Putin is about to teach it to him the hard way.
What is more risky Ms. Labott, for Trump to make a deal that looks like victory or to confront Putin now? History has shown that to kick the can down the road may result in a future of catastrophic events. Very good analysis. Take care.