Washington — Russian President Vladimir Putin gave President Trump’s special envoy Steve Witkoff an award to pass along to a senior CIA official whose son was killed in Ukraine while fighting alongside Russian forces, according to sources familiar with the matter.
The award, the Order of Lenin, was meant to be handed off to Juliane Gallina, whose 21-year-old son, Michael Gloss, was killed in 2024.
Gallina is currently serving at the CIA as deputy director for digital innovation. It could not be immediately determined what was done with the award.
Multiple sources told CBS News that Putin gave Witkoff the award during his trip to Russia this week, which a Russian official said the U.S. initiated, to discuss ending the Ukraine war.
The gesture by Putin, known for mind games and attempts to expose adversaries’ points of weakness, was likely meant to raise unhelpful questions and highlight that a CIA official’s son fought for Russia in the war.
GAVRIIL GRIGOROV/POOL/AFP via Getty Images 
In a statement in April, CIA officials said the death of Gallina’s son, who struggled with mental health challenges, was not a national security issue. Two sources familiar with the matter told CBS News there was no indication that Gloss had been recruited by the Russian government, and that the Kremlin did not appear to be aware of Gloss’s family background when it repatriated his remains.
Spokespeople for the White House, the CIA and Witkoff didn’t respond with comment for this article. A Russian embassy spokesman contacted by CBS News said there was no official comment, and no acknowledgement of the award has been publicly disclosed by the Kremlin or Russian Foreign Ministry.
Putin’s move comes at a sensitive time, as Mr. Trump has expressed increasing frustration with the Kremlin and has vowed secondary tariffs starting on Friday, even as negotiations are underway for a possible summit.
The Order of Lenin is a Soviet-era award meant to highlight outstanding civilian service. It has been given to high-level spies, including the U.K.’s Kim Philby, a double agent for the Soviet Union. Gallina’s son was never an employee of the CIA, according to a person familiar with the matter.
Putin, a former KGB operative, has met five times with Witkoff, who left real estate development to become Mr. Trump’s envoy for sensitive peace missions. Witkoff’s reliance in the past on Russian government translators during high-stakes diplomacy has drawn scrutiny.
A source familiar with the talks told CBS News that Witkoff had a U.S. government translator with him for the encounter on Wednesday, two days before Mr. Trump’s deadline for Putin to end the war or face severe financial penalties via sanctions. That same day, the Trump administration put an additional 25% tariff on Indian goods to punish New Delhi for continuing to purchase Russian oil.
Mr. Trump described the Wednesday meeting in Moscow as “highly productive.” The White House said the Russians were eager to continue engaging with the United States and said that secondary sanctions were due to be implemented on Friday. However, as of Friday afternoon, no such sanctions had been issued.
On social media, Gloss published posts of himself in Moscow and voiced his support for Russian troops. Russian media first published news of Gloss’ death in April. The CIA’s statement at the time said Gallina and her family had suffered “an unimaginable personal tragedy.”
An obituary for Gloss said he was “tragically killed in Eastern Europe” on April 4, 2024.
Gloss’s father, Larry Gloss, an Iraq War veteran, told the Washington Post in an interview that he and Gallina did not know their son was in Ukraine or that he had enlisted in the Russian army.
“Our biggest fear while we were waiting for him to be repatriated was that someone over there [in Moscow] would put two and two together and figure out who his mother was, and use him as a prop,” Larry Gloss said.
