In a story that blends tragedy, diplomacy, and personal grief, Russian President Vladimir Putin has posthumously awarded the Order of Courage, one of Russia’s highest military honors, to Michael Gloss—the 21-year-old son of CIA Deputy Director Juliane Gallina.
Gloss, who died while fighting alongside Russian forces in eastern Ukraine, was remembered for his bravery in the Donetsk region.
The medal was delivered in an unusually personal way: through Steven Witkoff, a special envoy for U.S. President Donald Trump.
According to reports, this was less about political maneuvering and more about one grieving father supporting another.
Witkoff himself lost his only son to an opioid overdose in 2011, a loss that shaped his decision to personally hand the award to Gloss’s parents.
Why the Order of Courage Matters
The Order of Courage is no small recognition. It is typically given to individuals who have shown outstanding bravery, whether in times of disaster, emergency, or war.
In Gloss’s case, the award honored his role in combat while serving in the Donetsk People’s Republic (DPR).
While the symbolism is powerful, the White House was quick to clarify that this was not an act of diplomacy, nor a message of alignment with Russia, but rather a deeply personal gesture between families bound by loss.
The CIA also echoed that statement, calling the exchange “a private family matter.”
Confusion Over the Award
The delivery of the medal was initially surrounded by confusion.
Early media reports wrongly claimed that Putin had asked the U.S. to deliver the Order of Lenin, a Soviet-era award that hasn’t been given since the collapse of the USSR.
Russian officials dismissed that claim, confirming it was always the Order of Courage.
Putin reportedly made the request on August 6, during Witkoff’s visit to Moscow.
Interestingly, that same trip paved the way for the planned Putin–Trump summit scheduled in Alaska later this month.
Who Was Michael Gloss?
Gloss’s story is one of contrasts. Raised in a family with deep ties to the U.S. military and intelligence services, he still chose an unconventional path.
After leaving college in 2023, he traveled widely—volunteering in Honduras, helping earthquake survivors in Turkey, and eventually making his way to Crimea and Moscow.
While in Russia, he began pursuing citizenship, even creating a profile on VKontakte, the country’s main social media platform.
There, he followed groups honoring Vladimir Lenin and shared videos of Putin.
Gloss eventually joined Russia’s 137th Airborne Regiment and was killed in April 2024 during an assault near Rozdolivka and Vesele.
A Family of Service
The Gloss family has long been tied to military and security service.
His mother, Juliane Gallina, is a decorated U.S. Naval Academy graduate who spent over three decades in intelligence before becoming the CIA’s Deputy Director for Digital Innovation.
His father, Larry Gloss, is a Navy veteran of the Iraq invasion and now runs a defense software firm that works with both the U.S. government and NATO.
Despite these American roots, Michael carved out a very different life—one that ultimately led him to fight, and die, on foreign soil.
Remembering Michael
In their obituary, the Gloss family painted a picture of a young man deeply guided by justice and compassion.
They described him as someone who noticed “the unseen in our community,” whether people, animals, or the environment.
“Michael had a profound sense of justice,” they wrote.
“With his noble heart and warrior spirit, he was forging his own heroic path when he tragically fell.”
For them, and for those who knew him, Michael will be remembered not just as a soldier, but as a son, a volunteer, and a young man determined to make a difference—even in the most unexpected ways.
