US special envoy Steve Witkoff met Russian President Vladimir Putin in St Petersburg on Wednesday, October 21, for about three hours, carrying the proposals that emerged from Tuesday's "very productive and constructive" talks with Ukrainian President Volodymyr Zelenskyy in Oslo — a diplomatic relay that Washington hoped could create a pathway to direct three-way negotiations between Kyiv, Moscow and Washington. Jared Kushner joined the St Petersburg meeting by video link.

A US official said the St Petersburg meeting aimed to "build on the progress" of the Norway talks, in what was shaping up as the most active stretch of American shuttle diplomacy on Ukraine in months — and one unfolding against a backdrop of open friction between Washington and Kyiv.

What happened in Oslo

Tuesday's session was hosted by Norwegian Prime Minister Jonas Gahr Støre, with Finland's President Alexander Stubb also present alongside Zelenskyy. Diplomats from the United Kingdom, France, Germany and Poland attended, along with NATO representatives. An anonymous US official said Ukraine brought "new ideas and proposals" that were discussed in detail, and that the parties made "meaningful progress" toward a coordinated approach to engaging Russia.

The talks covered what the official described as "key elements of a comprehensive peace framework": security guarantees for Ukraine, a post-war economic plan and a broader European security architecture. Zelenskyy said he had discussed "Article 5-like" security guarantees, referring to the NATO stipulation that an attack on one ally is an attack on all — a formula that would give Kyiv a Western backstop without full alliance membership.

Finland's Stubb said "genuine progress" had been made on proposals, while cautioning that patience was needed. Zelenskyy himself appeared guardedly optimistic about the process but not the outcome: "Steve Witkoff is going to Russia tomorrow. Let's see what Putin has to say," he said, according to the Times.

The meeting followed the Oslo diplomatic push that began earlier this week, and it came after Zelenskyy had pressed Secretary of State Marco Rubio in a 45-minute phone call about Ukraine's most urgent shortages. After that call, Zelenskyy told reporters that US intelligence sharing on incoming Russian missile attacks — which Kyiv had complained was being withheld — was flowing again. "Now it works, it's great," he said.

Trump's message to Kyiv: settle the war

The diplomacy landed alongside a sharper tone from the White House. Speaking in the Oval Office on Tuesday, Trump accused Ukraine of giving the United States "nothing but grief" and said it was "time for Ukraine to end this war."

"We've given a lot to Ukraine. We've gotten absolutely nothing back except grief, death, tremendous monetary loss," Trump told reporters, adding that Russia is "a big machine — they just keep grinding forward... they have an unlimited supply of people."

Trump has recently suggested Ukraine should have a new president and that someone else should negotiate on its behalf, and he again pressed Zelenskyy to "want to settle this war." The pressure campaign has alarmed European allies: EU foreign policy chief Kaja Kallas accused the United States of pressing Ukraine to surrender on Putin's terms, and Trump's recent gestures toward Moscow — including a deal to buy Russian diesel and a waiver of new sanctions — have drawn bipartisan pushback in the US Congress.

Since Trump and Putin last spoke by phone on October 9, the US president has eased sanctions on Moscow while increasing pressure on Kyiv to end a war that Russia started, according to USA Today reporting — a dynamic that will hang over everything Witkoff brings to the Kremlin table.

The prisoner on the agenda: Stephen Hubbard

Witkoff's trip carries a second, human track. Trump said on Tuesday that he is close to securing the release of Stephen Hubbard, a retired American English teacher from Michigan in his 70s who has been held in a Russian prison for more than four years.

Hubbard was living in Izyum in eastern Ukraine when Russia launched its full-scale invasion in February 2022. Russian forces captured him, and a Russian court later sentenced him to nearly seven years on mercenary charges. In January 2025 the US government officially designated him as wrongfully detained. His family has rejected the charges, pointing to his advanced age and his decades-long career as an educator.

"I've been talking to President Putin about Mr. Hubbard. I've been talking to him at length," Trump told reporters. "It's time to get Mr. Hubbard back." Asked whether a deal was close, he added: "Just remember that question for a couple of days from now."

A US official, speaking on condition of anonymity, said Witkoff's trip to Russia is also expected to include efforts to seek Hubbard's release, reflecting what the official called Trump's continued commitment to bringing detained Americans home.

Moscow's position: listening, but no concessions

Russia is entering the talks on maximalist terms. Foreign Minister Sergei Lavrov said the Kremlin would listen to what Witkoff brings but ruled out "any political concessions" — a signal that Moscow sees the battlefield, not the negotiating table, as the source of its leverage.

That leverage was on display overnight. Hours before Witkoff's trip, Russian drones killed two people near Ukraine's second-largest city of Kharkiv, regional governor Oleh Syniehubov said, with another 11 suffering stress reactions in an attack that struck private houses. In Kyiv, a Russian airstrike hit a high-rise apartment building and transport infrastructure, causing fires, while a strike on a university in Kremenchuk injured two, according to local authorities cited by Reuters.

The overnight strikes followed Tuesday's attacks, in which Ukrainian officials said at least 10 people were killed — four in Kyiv and the surrounding region, four in Donetsk and two in Dnipro, according to BBC reporting. Moscow has continued its bombardment of Ukrainian energy and civilian infrastructure even as the diplomacy accelerates, underscoring the gap between the negotiating track and the war on the ground.

The weapons question

Zelenskyy also used the Oslo week to press Washington on hardware. He told US senators this week that Kyiv was running out of ballistic-missile interceptors because, in his words, the Pentagon is delaying the delivery of missiles — a shortage that makes the held-up Patriot interceptor supplies one of the most consequential subplots of the diplomacy.

He raised the interceptor supplies and the satellite-based Starlink system — which Kyiv complained had stopped working when mounted on fast-moving objects such as drones — directly with Rubio, and later thanked the secretary of state on X for "his readiness to help and his clear position." The Elon Musk slowdown allegations around Starlink have added a commercial-political dimension to Ukraine's battlefield communications.

Why this meeting matters

The Witkoff-Putin meeting is the latest turn in a Trump-era diplomatic pattern: direct American engagement with Moscow that runs parallel to — and sometimes in tension with — the alliance with Kyiv. Trump and Putin have kept an unusually active channel since the US president returned to office, and each envoy trip tests whether personal diplomacy can bridge positions that remain structurally far apart.

For Ukraine, the stakes are existential: the "Article 5-like" guarantees on the table would be meaningless without credible enforcement, and Kyiv fears any settlement will freeze Russia's territorial gains in place. For Russia, the talks are a chance to lock in those gains while peeling Washington away from Kyiv. For Europe, watching from the sidelines of a negotiation about its own security architecture, the fear is that the United States will trade Ukrainian interests for a quick headline.

Witkoff's goal, per the US official, is to create "a pathway toward direct trilateral and broader multilateral negotiations." After the meeting, Kremlin foreign policy aide Yuri Ushakov said Putin had agreed in principle to resume trilateral talks at technical level, with Abu Dhabi proposed as a venue for around 10 November. A week later, Ushakov said Moscow had not yet proposed a specific date, casting doubt on whether the talks would take place in November as initially proposed. The next signal to watch: whether Putin offers anything Witkoff can take back to Kyiv, or whether, as Lavrov previewed, the Kremlin simply listens and waits. The Vatican has also appealed to Moscow directly: Pope Leo has urged Putin to open an aid corridor for the starving residents of Oleshky.

The talks opened with a humanitarian gesture, as Russia freed American Stephen Hubbard after Trump's appeal.

Sources: Reuters; Associated Press/AFP; The Times; USA Today; BBC; The White House.

Parallel humanitarian diplomacy has also borne fruit: a ceasefire brokered by Melania Trump opened the way for evacuating besieged Oleshky.