Trump's Ukraine Strategy Might Be Brilliant
Trump’s Ukraine Strategy Might be Brilliant
Trump’s Ukraine strategy is unclear. This is a good thing. If you are buying a house, revealing your bottom line weakens your position. You hide your enthusiasm, make an offer and look for tells. If your counterparty literally cannot walk away, and Ukraine can neither relocate nor cut ties with America, you can be pretty aggressive. Proclaiming the truth is not your goal, you want the best price. Trump’s actions so far are consistent with a perfectly coherent negotiating strategy. Whether he is following this strategy is uncertain but not unlikely. Let’s start with some basically uncontested facts.
Trump has repeatedly mischaracterized Ukraine’s leadership and the war’s cost and origins, calling Zelensky a dictator and blaming Ukraine for starting the war.
Trump wants Zelensky to accept a peace deal.
Zelensky wants to reconquer lost Ukrainian territory.
The present military situation is basically a stalemate. Russia is conquering territory at a very slow but steady rate. Ukraine shows little signs of immediate collapse but has very limited offensive capabilities.
Of these facts, Trump’s seemingly unhinged rhetoric is the hardest to explain. It’s just possible that Trump believes his own rhetoric. However, Trump probably isn’t that stupid. He graduated from Wharton, won the presidency twice and has pulled off the most astonishing political comeback since Nixon. He has shown a keen understanding of his own base and knows they won’t mind some rhetorical liberties at Ukraine’s Expense. Trump’s promise to protect Medicare and Social Security—when his party establishment wouldn’t—was the biggest shift in kitchen-table politics since Nixon’s Southern Strategy. Trump almost certainly knows he is lying. This begs the question why.
My theory is Trump understands his popularity would tank if Ukraine collapses. This is politics 101. Johnson escalated U.S. involvement in Vietnam despite doubts about victory, fearing that a communist takeover of South Vietnam would damage his presidency. Similarly, Biden’s approval ratings never recovered after the fall of Kabul in 2021. Trump likely understands that Ukraine’s collapse could be a political disaster for him. Trump also sees upside in peace. Finland made massive territorial concessions to Russia in 1944 and, over the next 30 years, became a rich and stable democracy. If Ukraine can survive, even in diminished form, and the killing stops, Trump might bolster its own prestige. He might also create a personal legacy and show the establishment hacks who the real man is.
Trump is trying to bully Zelensky into territorial concessions. To do this, he needs to establish a credible threat of withdrawing aid. However, he has to walk a tightrope because if Ukrainian morale withers and/or Ukraine lacks the material resources to continue the war, Russia might take Kiev and Trump’s popularity would plunge. Trump’s rhetoric has accomplished this. By its own admission, Ukraine needs more and better resources to reconquer territory. If it becomes obvious this won’t happen, Ukrainian public opinion might favor negotiations. Yes, Ukrainians might feel betrayed, but that doesn’t matter to Trump and doesn’t matter much to U.S. material interests.
Trump has multiple paths to victory. Even if the war continues, he might shift the cost of it to Europe. Perhaps Europe could arm Ukraine itself. Even better, it might buy weapons from the U.S. and give them to Ukraine. Eleven years after Russia annexed Crimea and began a proxy war in Donbas, Germany stlll spends just over 1% of its GDP on defense and France Germany and Italy about 2% each. This is not what collective security looks like. Most American voters like peace and hate being taken advantage of. Europe has a greater interest in containing Putin than the U.S.. If Ukraine survives at Europe’s expense, Trump also wins.
I’m 70% sure Ukraine will survive. It’s more likely than not that the outcome will help Trump politically, though this is less certain. Many moderate voters don’t like their President lying, and Trump’s shitposting might create pushback even from hawks in his own party.



But why does Trump want Ukraine to accept a peace deal that does not extract a high price on Russia for invading. A "pyrrhic" victory for Russia -- Russia and Ukraine both withdraw to their own territories (As Pyrrhus did at the end of the Pyrrhic War) -- the least that the US and Europe can accept without putting other countries at risk of coercion.
It’s always possible to come up with a story about why a seemingly dumb thing is actually smart if you’re willing to project thoughts to the actors and discount what they say they believe. This doesn’t make it impossible that “it’s all an elaborate ruse” is correct, but it’s probably better to view it as an outside chance.
In this case, Trump already has far more leverage over Ukraine than Russia. If he’s bluffing, he should be bluffing Putin. Just telling Ukraine “this war isn’t your fault but we’re done supporting you unless you accept this peace deal” would be just as effective, and without the lying and betrayal.