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August 19, 2025, 12:35 PM View Comments ()

After a strange, made-for-television summit in Washington on Monday meant to bring Russia’s escalating war on Ukraine closer to the conclusion that U.S. President Donald Trump vowed to achieve even before taking office, nearly all the big questions remain unanswered. Here are just a few of the major issues that the United States, Ukraine, its European backers, and Russia will be grappling with in days and weeks to come.

1. What security guarantees is Trump actually offering Ukraine?

On the campaign trail in 2024, Trump pledged not to commit U.S. troops to Ukraine. But during his Oval Office meeting with Ukrainian President Volodymyr Zelensky on Monday, Trump twice declined to rule out sending in U.S. troops to ensure Ukraine’s security as part of a final peace deal, raising hopes that he had perhaps changed his mind. 

However, on Tuesday, he once again ruled out having U.S. troops participate in any Ukraine peacekeeping force, though he said that Washington could potentially provide air support, and he suggested that Britain and France could take the lead in backstopping Ukraine’s sovereignty after any eventual peace deal. But even that is uncertain: The Russian Foreign Ministry rejected outright the idea of any NATO troops in Ukraine to shield the country from renewed Russian aggression. 

It’s also unclear what is meant by the notion of “Article 5-like” security guarantees for Ukraine that Trump envoy Steve Witkoff said Putin had agreed to at the Alaska summit. Article 5 is NATO’s mutual-defense clause; without the involvement of the trans-Atlantic alliance, there is no formal mechanism to bind any “coalition of the willing” to come to Ukraine’s future defense. Ukraine isn’t a member of NATO, and the apparent condition that Trump conceded after his Alaska meeting with Russian President Vladimir Putin about Ukraine never joining the alliance also raises questions about just how to guarantee the long-term security of Ukraine.

2. What good are these security guarantees when Ukraine watched the 1994 Budapest Memorandum and the 2015 Minsk accords be shredded by all signatories?

Ukraine and its European partners seem to be serious about nailing down U.S. and Western security measures for Kyiv, but Ukraine is twice-bitten and three-times shy. Shortly after the fall of the Soviet Union, and again shortly after Russia’s first invasion of Ukraine, the United States, Europe, and Russia all committed to guarantee Ukraine’s security and territorial integrity, and yet Russia still launched its full-scale invasion in February 2022. 

3. Will there be a bilateral meeting between Putin and Zelensky? Or a trilateral meeting including Trump?

Trump reportedly interrupted his follow-on meeting with European leaders late Monday to speak with Putin about a meeting with Zelensky. Yet it remains unclear if Russia—which has refused previous entreaties from Kyiv—would agree to such a meeting, and if so, where it would be held and what the agenda might be. Switzerland is angling to parlay its neutrality into hosting any meeting, but Putin (who is wanted for arrest on international war crimes charges) seems keen to avoid traveling to Western Europe. Istanbul looks to be an option, though Turkey has bad memories for Ukrainian negotiators weary of maximalist Russian demands.

4. Would Ukraine be able to countenance surrendering Crimea? What about the Donbas? 

Surrendering some territory for peace is an issue Zelensky has grappled with since 2022. Crimea, which Russia illegally annexed in 2014, in particular is tricky because Moscow has had a decade to consolidate its hold on the peninsula, as well as building a land bridge (and an actual bridge) to link it to other Russian-held territories. 

“If President Zelensky determines that he wants to let NATO membership go, and that he is willing to let Crimea go, I think the Europeans will accept it,” said Julianne Smith, a former U.S. ambassador to NATO. “My sense is that Zelensky would only accept those two terms in exchange for a whole long list of concessions on the Russian side, namely, some other form of a security guarantee.”

The eastern Ukrainian territories collectively known as the Donbas are trickier; some parts, such as Donetsk, are still battlegrounds and have not yet become Russian enclaves. And they are (or were) the heart of Ukraine’s coal and metallurgical industries, as well as a future hope for natural gas extraction. Hiving off the entirety of eastern Ukraine to appease Russia would leave Ukraine smaller, of course, but also with a hungry neighbor poised to use its new acquisitions as a launchpad for future land grabs.

There’s also the matter of Ukraine’s constitution, which bars the cession of national territory unless such a move is ratified by a nationwide referendum. Zelensky cannot just give away one-fifth of his country unilaterally. 

5. What would a U.S.-brokered agreement that legitimized the forcible redrawing of national borders do to the international system? 

The United States, at least beginning in the 20th century, used to be firmly opposed to wars of annexation; the First Gulf War was fought specifically to refute Iraq’s bid to snatch Kuwait through violence. U.S. administrations condemned Russia’s annexations of territory in Georgia and Ukraine early this century. 

But then, prior U.S. administrations didn’t openly entertain the idea of annexing Greenland, reclaiming the Panama Canal, or forcibly making Canada the 51st state. So that rules-based order might be dead already.

6. What would any peace deal do about reparations and war reconstruction? 

The United Nations already tabulates Russia’s damage to Ukraine at $524 billion and counting. 

Europe, the United States, and a few other countries still hold nearly $300 billion of frozen Russian Central Bank assets, which could be used to pay for part of the reconstruction. Yet there has been no public discussion of how those funds could fit into any peace deal. 

Then again, Putin is seeking economic relief from any peace agreement—he flew to Alaska last week hoping to rekindle economic ties with the United States and perhaps ease sanctions—and the staggering Russian economy is hardly in a position to underwrite Ukraine’s recovery, even if the Kremlin agreed to do so. That would likely leave the bill on Ukraine and its European neighbors.

7. What happens if all this diplomacy comes to naught?

Trump has previously said he would walk away from the Ukraine peace process if he can’t force an agreement. If Ukraine can’t abide national amputation, or if security guarantees don’t materialize, or if Russian peace overtures prove hollow after all, both sides may be back to the trenches by the autumn, not that they ever left. And Europe’s bloodiest war since World War II will continue, into another winter. 

When asked by a reporter in the Oval Office on Monday whether this was “the end of the road for American support for Ukraine … deal or no deal,” Trump replied: “I can never say that. It’s never the end of the road. People are being killed, and we want to stop that. So I would not say it’s the end of the road.” 

How much longer that road extends, though, is anyone’s guess.