Tom Sanders
Thu, August 21, 2025
The Daily Beast
Gavriil Grigorov/Pool/AFP via Getty Images
Trump envoy Steve Witkoff inadvertently helped Vladimir Putin troll the grieving family of an American man who was killed while fighting for Russia.
Michael Gloss was killed in Ukraine last year after traveling to Moscow and volunteering for the Russian military after dismissing criticism of their invasion as “Western propaganda.”
The 21-year-old, who reportedly struggled with severe mental health problems for most of his life, was later revealed to be the son of Juliane Gallina, the CIA’s deputy director for digital innovation, and Larry Gloss, an Iraq war vet and CEO of a security tech firm.
During a meeting with Putin on a trip to Moscow earlier this month, Witkoff was presented with an award for Gloss by the Russian president and instructed to present it to Gloss’ grieving family—a move considered by many to be a diplomatic slight, given his parents’ line of work.
Yet Witkoff, a real estate friend of President Donald Trump who had no diplomatic experience before becoming his special envoy to the Middle East and special envoy for peace missions, instead took Putin at his word and delivered the medal to Gloss’ relatives, with an administration source telling CNN he considered the matter to be one that transcended geopolitics.
The name of the award remains unclear—CNN reported Putin gave Witkoff the Order of Courage, while the BBC and CBS reported it to be the Soviet-era Order of Lenin, which recognizes outstanding civilian service.
In Witkoff’s eyes, the moment was “not about who he fought for, but rather the memories of our children and the overarching message of ‘Let’s end this war,’” the source said, also claiming that Gallina “wept with her husband” upon receiving the medal.
In a statement to CNN, the CIA said: “The entire CIA family is heartbroken for their loss. Juliane and her husband shared that ‘we adored our son and grieve his loss every moment. We appreciate privacy at this difficult time.”
“Juliane Gallina and her family suffered an unimaginable personal tragedy in the spring of 2024 when her son Michael Gloss, who struggled with mental health issues, died while fighting in the conflict in Ukraine. CIA considers Michael’s passing to be a private family matter for the Gloss family – not a national security issue,” they added.
Gavriil Grigorov/Pool/AFP via Getty Images
Trump envoy Steve Witkoff inadvertently helped Vladimir Putin troll the grieving family of an American man who was killed while fighting for Russia.
Michael Gloss was killed in Ukraine last year after traveling to Moscow and volunteering for the Russian military after dismissing criticism of their invasion as “Western propaganda.”
The 21-year-old, who reportedly struggled with severe mental health problems for most of his life, was later revealed to be the son of Juliane Gallina, the CIA’s deputy director for digital innovation, and Larry Gloss, an Iraq war vet and CEO of a security tech firm.
During a meeting with Putin on a trip to Moscow earlier this month, Witkoff was presented with an award for Gloss by the Russian president and instructed to present it to Gloss’ grieving family—a move considered by many to be a diplomatic slight, given his parents’ line of work.
Yet Witkoff, a real estate friend of President Donald Trump who had no diplomatic experience before becoming his special envoy to the Middle East and special envoy for peace missions, instead took Putin at his word and delivered the medal to Gloss’ relatives, with an administration source telling CNN he considered the matter to be one that transcended geopolitics.
The name of the award remains unclear—CNN reported Putin gave Witkoff the Order of Courage, while the BBC and CBS reported it to be the Soviet-era Order of Lenin, which recognizes outstanding civilian service.
In Witkoff’s eyes, the moment was “not about who he fought for, but rather the memories of our children and the overarching message of ‘Let’s end this war,’” the source said, also claiming that Gallina “wept with her husband” upon receiving the medal.
In a statement to CNN, the CIA said: “The entire CIA family is heartbroken for their loss. Juliane and her husband shared that ‘we adored our son and grieve his loss every moment. We appreciate privacy at this difficult time.”
“Juliane Gallina and her family suffered an unimaginable personal tragedy in the spring of 2024 when her son Michael Gloss, who struggled with mental health issues, died while fighting in the conflict in Ukraine. CIA considers Michael’s passing to be a private family matter for the Gloss family – not a national security issue,” they added.
Steve Witkoff presented the medal to Gloss’ family following a meeting with Putin. / Anna Moneymaker / Getty Images
Earlier this year, Michael’s father, Larry Gloss, told The Washington Post about his son’s struggle with mental illness and said it was “absolutely news to us that he was involved in any military relationship with Russia.”
Their son, he said, was “the ultimate anti-establishment, anti-authority young man the minute he came into the world,” and traveled to Russia after he became convinced the country was the only place he could accomplish his dream of “building a water purifier” to help people without access to clean water.
“I can only attribute it to his mental illness,” the father said. “It clearly defies logic.”
Gloss was killed during an artillery strike on Russian troops in the Donetsk region. / Libkos / Getty Images
Gloss eventually died from a “massive blood loss” caused by an artillery strike in Donetsk last April, with his remains repatriated to the U.S. in December.
His parents were fearful during that time 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,” Gloss’ father said, but a Kremlin source later told CBS that they were not initially aware of his family background.
The Daily Beast has contacted the White House for further comment.
Witkoff delivered Russian medal from Putin to family of American who was killed fighting for Russia in 2024
Jake Tapper, CNN
Wed, August 20, 2025
US Special Envoy Steve Witkoff waits for the start of a press conference between US President Donald Trump and Russian President Vladimir Putin at Joint Base Elmendorf-Richardson in Anchorage, Alaska, on Friday. - Andrew Harnik/Getty ImagesMore
US special envoy Steve Witkoff delivered a Russian medal to the grieving family of an American who was killed fighting for Russia in 2024, a senior administration official told CNN.
Earlier this month, when Russian president Vladimir Putin gave the medal – the Order of Courage – to Witkoff, some observers saw it as something of a diplomatic dig, given that the American who was killed, Michael Gloss, 21, was the son of a senior CIA official.
But that wasn’t how Witkoff saw it. The Order of Courage is a Russian Federation decoration typically given to Russian citizens to recognize selfless acts of courage and valor during times of emergency, disaster and war. For Witkoff, who lost a son in the opioid epidemic, losing a child is a traumatic experience that transcends geopolitics. And he thought it worthwhile to give the medal to Juliane Gallina, the CIA’s deputy director for digital innovation, and her husband, according to the official.
“She wept with her husband,” the senior administration official told CNN.
For Witkoff, the moment “was not about who he fought for, but rather the memories of our children and the overarching message of ‘Let’s end this war,’” the official told CNN.
A CIA spokesperson issued a statement to CNN: “The entire CIA family is heartbroken for their loss. Juliane and her husband shared that ‘we adored our son and grieve his loss every moment. We appreciate privacy at this difficult time.’”
“Juliane Gallina and her family suffered an unimaginable personal tragedy in the spring of 2024 when her son Michael Gloss, who struggled with mental health issues, died while fighting in the conflict in Ukraine. CIA considers Michael’s passing to be a private family matter for the Gloss family – not a national security issue,” the spokesperson said.
Witkoff has played a significant role in the US effort to end Russia’s war in Ukraine, including sitting alongside President Donald Trump in his summit with Putin in Alaska on Friday.
He told CNN that the leaders made “game changing” agreements related to security guarantees for Ukraine, though questions remain about how serious Putin is in pursuing a peace agreement.
Witkoff traveled to Moscow this month to meet with Putin, and also played a role in talks with top Russian and Ukrainian officials held in Saudi Arabia earlier this year in order to work towards ending the war.
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