Trump’s recent summit with Vladimir Putin in Anchorage, Alaska, ended not in toughness but in capitulation. Despite pledging red lines beforehand, Trump rolled out the red carpet, and has now appeared to endorse Moscow’s demands for the surrender of Ukrainian territory. In this week’s episode of the Washington Monthly politics roundtable, special guest Tamar Jacoby, Director of the New Ukraine Project at the Progressive Policy Institute, shares reaction on the ground in Kyiv to Trump’s betrayal of Ukraine. She also suggests steps Trump should be taking instead to regain the advantage over Putin.
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This transcript has been edited for length and clarity.
Paul Glastris: On Friday, President Trump had a shameful face-plant of a summit meeting with Vladimir Putin in Anchorage, Alaska. He then invited Ukrainian president Volodymyr Zelensky to the White House today, along with a team of European leaders—including the European commissioner, the head of NATO, and the presidents of France and Germany—who insisted on coming to back Zelensky and try to persuade Trump to take a tougher line than he certainly did in Anchorage.
That’s what we’re here to discuss. I want to start with you, Tamar. You are the guest of honor. In your story, you explained that in the run-up to the Anchorage summit things were relatively quiet, but in Kyiv and elsewhere in Ukraine, that wasn’t the case last night. Tell us—are you safe, and what’s happening on the ground?
Tamar Jacoby: Yes, I’m safe. Kyiv is well protected by air defense. The scary air alerts do happen, but we haven’t had one in two weeks. Even when they come with great intensity, it’s every other or every third night. Life goes on in Kyiv—people are out in bars and restaurants. It’s a beautiful late summer.
Elsewhere in Ukraine, not so much. Last night was bad in some places, though not here. The week before the Alaska meeting was actually a good week, because Putin was trying to behave, and we all got a full night’s sleep for more than a week. It was noticeable—you realize how much stress people are under when suddenly there’s relief. Everyone was different, much more cheerful.
But you’re right: the most important thing is the shameful concessions Trump is making, pressuring Ukraine hard. It really is back to: give Putin whatever he wants.
Paul Glastris: So we went into this summit on Friday where the Europeans and Zelensky had discussions with Trump about what he would do. What were the red lines, and how were they reversed?
Tamar Jacoby: He agreed to some red lines, including that Ukraine would not have to give away territory Russia hasn’t conquered. Many Ukrainians are reluctantly coming around to the idea that they might have to forego the land Russia already holds. But we’re also talking about an area bigger than the West Bank that Russia has been trying—and failing—to conquer for 10 years.
We went into Alaska with Trump seeming to understand that it was important to get a ceasefire before detailed talks, and that security guarantees for Ukraine were critical. There were many things he seemed to get. But in Alaska, he didn’t seem to remember any of them. Instead, he rolled out the red carpet, stood there laughing with Putin, and even had an air salute overhead—for a man who’s been an international pariah, killing tens of thousands of people for four years.
Two big concessions stand out. First, Trump seems to have agreed with Putin that a ceasefire isn’t important—that Putin can go on killing until a full peace is reached, which only increases pressure on Ukraine. Second, and worse in my view, Trump now appears to be pressuring Ukraine to give up the remaining half of Donetsk—a region Russia has fought over for more than a decade without real success. That would mean giving it away for free, soil watered with the blood of countless Ukrainian fighters.
But the war isn’t really about territory. It’s about whether Ukraine can exist as an independent country, with the political system and alliances it chooses. Putin stood on stage in Anchorage, 15 feet from Trump, and repeated those demands. Trump nodded along. We’re talking about a return to Cold War-style divisions of Europe—except now Russia doesn’t even control that territory with troops, yet we may hand it to them.
Paul Glastris: Let me ask about one detail: a lot of reporters noted the meeting ended very early. There was supposed to be a longer press conference or even a second round of discussions. Instead, it wrapped up abruptly, and Trump’s aides looked ashen-faced—hardly pleased with what they’d heard. What have you heard about that? What do you make of it?
Tamar Jacoby: I don’t have inside knowledge, so I can only speculate. My guess is that Trump initially thought he’d suffered a blow. He went in wanting a ceasefire and came out without one. At first, I think he took that as a failure. But over the weekend, he seems to have decided he could spin it as a win if he simply gave in to Putin.
That’s the point: Trump talks tough but, when rebuffed, capitulates. And at root, he’s always admired Russia as a “great world power.” For forty years, he’s wanted to be Putin’s equal, to do business with Russia. That motive has never gone away.
The press conference was revealing. It was short—twelve minutes—and light on details. But the end was all about business deals, both men talking about opportunities to work together commercially.
Paul Glastris: Before we turn to today’s developments, I want to linger on the fallout here in Washington. Bill, you track this closely. As you watched coverage after Friday, what struck you?
Bill Scher: What struck me is how sterile the coverage has been. Commentators have treated it neutrally, but this is seismic. Trump is trying to turn back the clock to a pre–World War I world, when a handful of leaders drew maps at whim. We fought two world wars to get away from that.
Woodrow Wilson, whatever his flaws, fought for self-determination and the League of Nations. FDR and Truman carried that vision forward, and after World War II the idea took hold: borders couldn’t just be changed by force.
Now it’s the European leaders who want to uphold that order, while Trump is pulling the U.S. in the opposite direction. It’s shocking—he is 180 degrees away from the U.S. position of the last century.
Paul Glastris: I was texting with a national security friend and asked: if you put 100 GOP-aligned military leaders in a room and promised anonymity, how many would back Trump’s policies toward Russia? He said zero. And half would want Trump jailed.
This can’t be what many Republican officials actually believe in. Bill, Matt—have you seen any pushback from elected Republicans or senior party figures?
Matthew Cooper: Some. In recent weeks, when Trump briefly struck a tougher tone on Putin, Republicans showed a little more backbone. The Senate even passed a sanctions resolution with 85 votes. That suggests their innate hawkishness hasn’t vanished.
But it’s inconsistent. For example, Alaska Senator Dan Sullivan has been vocal about Russian and Chinese patrols near Alaska, but overall Republicans seem reactive—they only show toughness when Trump does. They’re not going to push him. And the Europeans know that, which is why they’re pressing him directly today.
The question is whether Trump is a “pillow”—malleable, shaped by the last person in the room—or whether he’s truly in Putin’s camp. Hard to say. Maybe today he’ll swing back toward Kyiv, maybe not.
For context, think back to 1986. Reagan and Gorbachev failed to reach a nuclear deal at Reykjavik, and hawks were relieved. Contrast that with last weekend: many were relieved there was no deal, believing Trump might have held his ground. That relief evaporated when he pivoted over the weekend.
Tamar Jacoby: I agree with Matt—we should see what happens today. But Bill captured the risk best: we could be sliding back to pre–World War I map-drawing, ignoring peoples’ rights.
My impression is that Trump doesn’t even understand that dimension. At the press conference, Putin laid out his vision, and Trump looked like he barely grasped it. Instead, he’s focused narrowly on land-for-security guarantees—whether Ukraine gives up Donetsk in exchange for promises.
That may be all he sees. After all, this is the man who once said, “If I want Greenland, I should have it.” He doesn’t see anything wrong with the very idea that horrifies us. And because he sets the terms of debate, today’s White House meeting will likely focus on the land swap and guarantees—while the bigger issue of Ukraine’s sovereignty, the “root causes” as Putin calls them, may not even be discussed. That’s frightening.
Paul Glastris: I’ve watched Trump’s statements over the last few months. He said he was “very upset with Vladimir Putin,” even used the word “bullshit,” and hinted at tougher sanctions and weapons for Ukraine. Some people thought maybe he’d really changed. Others said he was just lying.
Anchorage proved the cynics right. He told people what they wanted to hear, then sold Ukraine out.
Tamar, especially—you’ve written about what actually needs to be done. Tell us: what are the Europeans trying to get Trump to do, and what do you think really needs to happen?
Tamar Jacoby: We’ll see what the Europeans can do. The challenge is to reframe the conversation without provoking Trump. You can’t just tell him he’s wrong. You have to play to him. The question is whether they’ll be strong enough to hold their ground.
What should happen is clear. There’s an “easy peace” and a “hard peace.” The easy peace is giving Putin what he wants. That’s what Trump is proposing. It would end the war in weeks and win him the Nobel Peace Prize.
The hard peace is forcing Putin to negotiate in good faith by raising the costs of war. That means real military pressure, real economic pressure, and sustained U.S. and European commitment. So far, we’ve helped Ukraine but wavered on the endgame. Every time Trump flips, Putin concludes we’re unserious. He needs to know pressure will continue until he changes behavior.
Right now, he has no reason to believe that. A German think tank recently calculated what the war costs Western countries: less than 0.2 percent of GDP. That’s peanuts. Germany spends more on bus subsidies. It looks like a pet project, not an existential fight. For America, maybe it is—but for Europe, it absolutely is existential.
Matthew Cooper: It’s worth making explicit: even if Ukraine gave up Donetsk, the war wouldn’t end. Putin’s ambitions won’t stop there.
Tamar Jacoby: Exactly. Donetsk is the high ground, the fortified strategic area from which Russia could launch further attacks. If Putin gets it, he’ll be positioned to take more in a few years.
Right now, some in Washington are talking about trading Donetsk for “serious” U.S. security guarantees. But Russia has already signed guarantees with Ukraine and Europe—and thrown them away. And Trump hasn’t delivered a single bullet to Ukraine beyond what Biden already had in the pipeline. Why would anyone trust his word?
Paul Glastris: It feels like once the debate turns to “security guarantees,” we’ve already lost. We’re down to dotting the i’s and crossing the t’s on a meaningless piece of paper—peace in our time.
Bill Scher: If I were Ukraine, I’d hold out until the Trump presidency ends. His word is worth nothing. Remember the Iran nuclear deal: Obama struck it, Iran complied, and Trump tore it up anyway. Why trust him now?
If Ukraine can hold out for three years, maybe the American people will throw Trump out and you’ll get a partner you can trust, at least for a while. That’s still risky—but better than cutting a deal with someone who can’t be trusted at all.
Tamar Jacoby: A lot of Ukrainian soldiers feel the same. They’re determined to keep fighting, even if it means revolting against Zelensky should he try to compromise. But they will need U.S. intelligence, and they will need Europe to keep buying American weaponry. If Trump cuts that off, it’ll be very hard to last three years.
Matthew Cooper: Don’t forget Trump’s grudges. The first impeachment was about Ukraine. He still resents that, and he holds grudges forever. That, more than anything, colors his policy.
Paul Glastris: But let me push on that. Is it possible Trump feels humiliated now—like he lost? He’s about to be surrounded by European leaders who will flatter him, tell him he’s the great peacemaker, the one who deserves the Nobel Prize. Could that change his behavior?
Matthew Cooper: Sure. His ego is fragile. The Europeans won’t tell him he lost; they’ll tell him he’s already winning. They’ll remind him Teddy Roosevelt won the Nobel for brokering peace. They’ll feed him praise, call him strong, call him decisive. With Trump, it’s child psychology.
Tamar Jacoby: They’ll even call him “daddy.”
Paul Glastris: [Laughs] And he’ll like it. Tamar, what’s the best realistic scenario coming out of today’s meeting?
Tamar Jacoby: That Trump realizes Putin is demanding far more than he’s taken so far, and that he starts listening to the Europeans instead of swinging back and forth.
The bare minimum would be returning to the status quo from a month ago: the U.S. sells weapons to Europe to give to Ukraine, continues intelligence support, and imposes real economic costs on Russia. That means cutting off oil revenues—40 percent of Russian exports, a third of its budget—and blocking the flow of Western technology that keeps missiles flying.
It’s not rocket science. It’s military force, economic isolation, and resolve. Without that, Putin won’t stop.
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