Putin Frees American Stephen Hubbard, Agrees to Resume Trilateral Talks After Nov. 10. Russia Hits Kyiv With 21 Missiles Overnight

Since Steve Witkoff's Tuesday meeting with Volodymyr Zelensky in Oslo, the Trump administration's Ukraine diplomacy has produced one concrete result and one promise. The result: an American prisoner is free. The promise: Vladimir Putin says he will return to the table after Nov. 10.

Then came the missiles.

An American comes home

On Wednesday, Oct. 21, Putin told Witkoff in St. Petersburg that Stephen Hubbard was already preparing to board a flight to the United States. Hubbard is a 74-year-old Michigan native, Air Force veteran and retired teacher. He had been held in Russia for more than four years on charges of fighting as a mercenary for Ukraine and was sentenced to six years.

Washington had maintained he was wrongfully detained. A White House official described him as the last American officially designated as wrongfully detained by Russia and the third American prisoner Russia has released during Trump's second term.

Trump said he asked Putin directly in a phone call last week. On Truth Social he wrote that the U.S. "was not required to give anything in return," adding that "there was no 'swap' necessary for this release."

Hubbard's younger sister, Patricia Hubbard Fox, told the Associated Press she spoke with him after his release. She said he told her he thought he was "going to die in prison" and that he suffered beatings and starvation in custody.

Whatever Moscow's motives, a 74-year-old American is out of a Russian prison, and Trump says the U.S. gave nothing in return. That is a real result.

Talks 'in principle' after Nov. 10

The Witkoff-Putin meeting at the Constantine Palace lasted about three hours, the Kremlin said. Russian presidential envoy Kirill Dmitriev and Putin's foreign policy aide Yuri Ushakov were at the table. Jared Kushner took part by video link, Ushakov said.

According to a White House official, Witkoff and Kushner proposed a technical-level trilateral meeting among the U.S., Russia and Ukraine. The official said Ukraine accepted it in Oslo on Tuesday and Russia accepted it in St. Petersburg on Wednesday.

Ushakov said Putin agreed "in principle" to resume talks after Nov. 10, and that they would focus on "building a security system for Russia and Ukraine after the conflict ends." He said the next round could be held in Abu Dhabi. The Kremlin offered no further details on what Russia would demand as part of that framework.

The last trilateral talks came in three rounds earlier this year: two in Abu Dhabi and one in Geneva. PBS reported little progress beyond exchanges of prisoners of war. The Moscow Times reported that talks have been stalled since February, when Trump ordered attacks against Iran.

The 'humanitarian' remark

Witkoff's tone with Putin drew immediate attention. During the televised portion of the meeting, he said: "You talk so much about my president, President Trump, being a humanitarian. You are a humanitarian also, sir, and I salute that."

Putin is wanted by the International Criminal Court as a war criminal in relation to the deportation of Ukrainian children to Russia. The UN has confirmed more than 17,500 civilian deaths in Ukraine since the February 2022 invasion and says the true toll is likely significantly higher.

Witkoff also conveyed Trump's thanks for a deal to resume Russian diesel exports to the U.S. and said it would help reduce prices for American farmers and truckers. Six Republican senators joined Democrats in urging Trump to reverse the diesel decision, and five House Republicans signed a separate bipartisan letter seeking to revoke the Treasury authorization.

John Hardie, deputy director of the Russia Program at the Foundation for Defense of Democracies, told Fox News Digital that easing pressure on Moscow before securing a reciprocal energy ceasefire could encourage Putin to hold out for further concessions. "The Ukrainians could stomach it if it were part of a mutual energy truce where both Russia and Ukraine don't strike each other's infrastructure," Hardie said.

Kyiv under fire

Overnight into Thursday, Oct. 22, Russia launched 21 missiles and 210 drones at Ukraine. Zelensky said the strikes killed two people and injured 34 in Kyiv, and Ukrainian officials said central Kyiv was also hit with a cluster warhead.

The Ukrainian Air Force said none of the ballistic missiles that hit Kyiv were intercepted. Ukraine is facing a critical shortage of US-made Patriot defense missiles.

"When Russian ballistic missiles are the response to negotiations, real pressure must be applied on Russia to take other steps – steps to stop the killings," Zelensky said, calling for rapid delivery of air defense missiles.

CNN reported that the first explosions hit Kyiv three minutes before Trump told reporters on Wednesday that his administration is "the closest we've been" to settling the war.

Russia absorbed its own barrage. Moscow's mayor said 630 drones flew toward the Moscow region overnight, most of them intercepted, in an attack that injured two people in the rural Voronovo area.

What Moscow is still demanding

CNN reported there are no indications so far that Russia has budged on any of its maximalist positions. Moscow has demanded that Ukraine give up the entire eastern Donbas region, which is now mostly under Russian occupation, dramatically reduce the size of its military and pledge never to join NATO.

Zelensky told Fox News in an interview broadcast Wednesday that freezing the conflict is the "minimum" required from Russia. He has insisted that only a summit of leaders can break the impasse.

Ushakov also said that while Witkoff had highlighted new approaches from the Europeans and Kyiv, "in truth, these contained little of actual value for resolving the Ukrainian crisis."

The Guardian characterized Hubbard's release as appearing to be a calculated Russian move to bring Trump further into line with Putin's position, while offering him a diplomatic victory before the midterm elections. The White House official said the Oslo and St. Petersburg discussions reflected a "positive and constructive spirit."

It is unclear whether Putin shows up with anything new. Putin's commitment to resume talks is only "in principle," it is tied to the period after Nov. 10, and the next round could be held in Abu Dhabi. Air raid sirens continued to sound in Kyiv on Thursday, with warnings of further incoming ballistic missile attacks.