Russia Frees American Stephen Hubbard as Witkoff Meets Putin in St. Petersburg

A day after Steve Witkoff met Volodymyr Zelensky in Oslo, Russia has freed Stephen Hubbard, the retired Michigan teacher imprisoned on charges of fighting as a mercenary for Ukraine. Witkoff announced the release as he arrived in Russia for talks with Vladimir Putin.

Who Hubbard is

Hubbard, 72, was sentenced by a Moscow court in October 2024 to almost seven years in prison. Russian prosecutors said he signed a contract with the Ukrainian military after Russia's February 2022 invasion and fought alongside Ukrainian troops until he was captured about two months later.

President Trump had signaled the outcome on Tuesday, Oct. 20. "I've been talking to President Putin about Mr. Hubbard. I've been talking to him at length. I've asked him to release him," he said.

In the Oval Office he added: "Everybody's been after Hubbard for a long time, long before I got here, and just remember that question for a couple of days from now. You know why? Because I do things that nobody else can."

Russia's Foreign Ministry confirmed Tuesday that it was talking with Washington about a possible prisoner release. It gave no further details.

The Putin meeting

Witkoff is meeting Putin at the Konstantinovsky Palace in St. Petersburg on Wednesday, Oct. 21, with Kremlin investment envoy Kirill Dmitriev present, according to Russian state media. Jared Kushner did not travel because of illness and was expected to join remotely.

In the opening exchange relayed by TASS, Putin said he wanted to restore ties and economic cooperation with the US. He praised the diesel deal with Trump.

Witkoff said he hoped Putin would agree to resume talks with the US and Ukraine for "technical discussions." He described the Oslo meeting as productive, with "a foundation in place to move toward a ceasefire."

A US official told Axios that Witkoff would present an updated proposal. The White House hopes Putin will compromise after Trump agreed to lift sanctions on Russian diesel sales and took other steps Moscow welcomed.

Russian presidential aide Yuri Ushakov was cautious. "I don't know if any agreement will be reached today," he said. Foreign Minister Sergey Lavrov has said Russia will listen to US proposals but rules out political concessions, according to TASS.

Putin has also demanded that Ukraine cede full control of the Donetsk region as a precondition for any ceasefire. Kyiv has repeatedly rejected that.

Kyiv's position

At Oslo on Tuesday, alongside the leaders of Finland and Norway, Zelensky said the talks were constructive and that Washington had reaffirmed security guarantees. He said the discussion covered NATO's Article 5 and "different kinds of security guarantees" that Witkoff would carry to the Russians.

He also said Ukraine would accept a deal only with Kyiv at the table. "Nothing about Ukraine without Ukraine," he said. He raised with US officials the reported idea of a trilateral meeting of the US, China and Russia on ending the war.

Zelensky confirmed that US intelligence sharing had resumed, calling it "very, very important." He said progress on Patriot interceptors and Starlink restrictions could come within 48 hours.

A source with knowledge told Axios that Kushner, on the Oslo call, again pressed Trump's demand that Ukraine stop striking Russian oil refineries.

Washington's own friction

Hours after the Oslo meeting, Trump said Ukraine "has to want to make a deal." He claimed Washington and Europe had spent "a fortune" on Kyiv, and said the US had received "nothing back other than high diesel." He also said he thinks "Russia would like to get it done" but doubts Zelensky wants to end the war.

Kyiv rejects the claim that it is obstructing peace. It says it has backed ceasefire proposals and offered a full ceasefire and direct talks with Putin. Zelensky argues that Washington's easing of sanctions on Russia, including the diesel deal, risks prolonging the war.

Senator Thom Tillis, a Republican, has questioned delays in Patriot transfers to Ukraine. He also said Putin is playing Trump "like a fiddle," as Russian strikes kill civilians.

Trump announced an "energy ceasefire" on Oct. 11. Ukraine paused strikes on Russian energy targets for three days, then resumed them, citing continued Russian attacks. Overnight Russia again hit energy and civilian targets across Ukraine, causing at least one casualty, according to local media.

There is also a dispute over Starshield, SpaceX's military-grade Starlink service. Zelensky accuses Washington of slowing it. Secretary of State Marco Rubio said Trump had "nothing to do with the decisions that are made by Starlink and Starshield." Elon Musk says only the US military and the president can make such decisions. The Wall Street Journal reported Tuesday, citing US officials and people familiar with the matter, that Musk ordered the slowdown.

What comes next

Hubbard's release is a concrete result for one American family. The war's terms are another matter. Zelensky said Tuesday, "We will hear his feedback in one day." Whether Putin moves off the Donetsk demand, or only agrees to technical talks, is the question the St. Petersburg meeting is meant to answer.