Cosmopolitians! In case you missed it, check out my Substack Live on World Review with
and on next steps in Ukraine. It was a lively discussion that dissected the week’s frantic diplomacy, but also takes the conversation on Ukraine forward. It was great to be Yasmeen, who has covered the White House for years and has a sharp perspective on how this White House operates. Thanks to Ivo for hosting, and look forward to returning the favor and having him here on Cosmopolitics and I will be back today at 5:30 ET/2:30 PT for Hot Takes Happy Hour. We are calling this the Let’s Make a Deal Edition, and I’m sure we will have some creative ideas about what Putin deserves behind doors # 1, 2 and 3.
Donald Trump's approach to ending the Ukraine war resembles nothing so much as a reality TV producer who's lost the script halfway through filming. He improvises wildly from scene to scene, treats every meeting like a photo opportunity, and seems genuinely surprised when the other contestants don't follow his made-up rules. The only problem? Putin isn't playing reality TV - he's playing chess, and he's been at it for two decades.
The combination of that bizarre summit in Alaska with Vladimir Putin and the only slightly less surreal gathering of NATO leaders in Washington was the latest reminder that Trump operates as a well-meaning amateur in a professional's game. He doesn't prepare, doesn't have subordinates lay the groundwork beforehand, and arrives at each meeting not knowing what he wants or where his red lines are. He has no strategy and isn't interested in the details, so he just improvises as he goes.
Trump's Ukraine "peace process" is fundamentally a personal quest to win a Nobel Prize and, apparently, help him get into heaven. He genuinely wants to stop people from dying. "If I can get to heaven," he told FOX and Friends, "this will be one of the reasons." Yet his approach treats Ukraine like a particularly complex real estate transaction rather than a nation of 40 million people fighting for their survival.
In the Fox & Friends interview following his White House meetings, he demonstrated a grasp of Ukrainian history that would embarrass a high school student. The war, he explained, started because of Crimea and NATO - echoing Putin's early propaganda talking points that even the Kremlin has largely abandoned. He described Ukraine as existing merely as a "buffer" with the West and suggested that Ukrainian demands to return their own territory were "very insulting" to Russia. Most remarkably, he seemed to blame Ukraine for the conflict, noting "You don't take on a nation that's 10 times your size" - apparently unaware of who actually invaded whom.
This isn't just ignorance - it's a combination of unwillingness to learn and surrounding himself with advisors who either won't educate him about the region or are afraid to contradict his preconceptions. Trump's seat-of-the-pants approach becomes genuinely dangerous when the person improvising doesn't understand the basic facts of the situation and shows no interest in acquiring them.
The most telling detail about Trump's summit prep? His special envoy Steve Witkoff, a New York real estate developer whose knowledge of Russian culture may not extend much beyond the borscht at the Russian Tea Room on 57th Street, reportedly misunderstood Putin's core demands in spectacular fashion. When Russia demanded Ukrainian "peaceful withdrawal" from contested regions, Witkoff apparently interpreted this as an offer of Russian withdrawal from those same territories—essentially hearing the exact opposite of what Putin was actually proposing. This kind of fundamental miscommunication could have been avoided entirely if Trump had proper briefings beforehand. If he'd known the Russians weren't budging on their maximalist demands, the summit could have been a phone call and Trump could have spared himself the embarrassment.
Meanwhile, Secretary of State Marco Rubio - who actually understands how real diplomacy works - is now working with Europeans on security guarantees for Ukraine, which offers some hope for a coherent formula. But Rubio seems to vacillate between acknowledging that negotiations are inherently difficult while giving the president credit for trying to end a devastating war, and attempting to justify the very Putin talking points that Trump has absorbed. Successful negotiations like those at Dayton or Camp David have one thing in common: they're meticulously prepared with advisers and working groups for weeks, if not months, to lay the groundwork for success. Rubio knows this playbook - the question is whether he can execute it while managing the expectations of a president who prefers dramatic gestures to patient groundwork.
What Putin accomplished in Alaska was breathtaking in its audacity. He got Trump to abandon his pre-summit demand for an immediate ceasefire, embrace Russia's preferred timeline for a "sweeping peace agreement," and essentially give Moscow permission to keep bombing Ukrainian civilians while they negotiate. In exchange, Putin offered exactly nothing - no territorial concessions, no meaningful commitments, just vague promises about "security guarantees" that he's broken repeatedly over two decades.
The trolling was genuine and immediate. On Monday morning Russian state media posted a video of what appeared to be a U.S.-made armored personnel carrier flying both American and Russian flags. The vehicle had allegedly been captured from Ukrainian forces and was now being used to attack Ukraine. The message was clear: America and Russia were now on the same side against Ukraine. Foreign Minister Sergey Lavrov showed up to the summit wearing a sweatshirt emblazoned with "CCCP"—the Cyrillic letters for the Soviet Union. Not exactly subtle.
Here is where it really gets absurd. Russia wants a say in Ukraine's security guarantees and wants territory it doesn't currently control. Putin's demands amount to asking Ukraine to cede regions where Russian forces have failed to achieve full control, while granting Russia veto power over Ukraine's future defense arrangements. It's like asking the burglar to help design your home security system.
Is Trump willing to give Russia back Alaska? Because that's the historical precedent Putin's invoking—the idea that territories can simply be transferred between great powers when it's convenient. Putin even suggested that Zelensky travel to Moscow for talks, a proposal so far-fetched that it revealed Russia's true contempt for the entire process.
As much as Europeans need to have Ukraine’s back, they also need to have Trump's—not because he doesn't want concessions from Putin, but because he can't get them. Trump isn't just an admirer of Putin or naive about Putin's motives; he's genuinely intimidated by him. Every time Trump sits across from Putin, he transforms from America First strongman to star-struck fan boy, eager to please a man who has spent decades perfecting the art of manipulating American presidents.
The sight of Ukrainian President Zelensky thanking Trump fifteen times in four and a half minutes during their White House meeting on Monday wasn't diplomatic courtesy - it was the desperate performance of a leader trying to prevent his country from being sold out by an American president who mistakes flattery for friendship.
Trump does have leverage. He could use it. But instead of wielding America's substantial economic and military advantages, Trump was seduced by Putin's personal charm and the fantasy that he could solve Europe's most complex crisis through pure charisma. Putin will eventually show his true colors again—he always does—but by then, how much Ukrainian territory will have been bargained away?
Putin didn't go to Alaska seeking peace—he went seeking a piece of Ukraine, preferably the whole piece if he could get it. Until Trump understands that fundamental difference, his peace process will remain what it's always been: great television, misguided diplomacy, and a gift to Vladimir Putin that keeps on giving.
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