Putin needles U.S. by giving Trump envoy an award meant for CIA official whose son died fighting for Russia

Russian President Vladimir Putin has taken a provocative step by awarding President Trump’s special envoy, Steve Witkoff, with the Order of Lenin, an honor typically reserved for high-level spies and civilians who have made significant contributions to the Soviet Union. The award was meant to be given to Juliane Gallina, a senior CIA official, whose 21-year-old son, Michael Gloss, died in 2024 while fighting alongside Russian forces in Ukraine. Gallina, currently serving as the deputy director for digital innovation at the CIA, is now the recipient of the award, though it remains unclear what happened to it after being passed to Witkoff.

According to sources familiar with the matter, Putin presented the award to Witkoff during his recent visit to Russia, which was initiated by the United States to discuss ending the Ukraine war. This move by Putin, known for his strategic mind games and attempts to expose adversaries' weaknesses, is believed to be a calculated effort to raise uncomfortable questions about the CIA official’s son and his involvement in the conflict.

Gallina’s son, Michael Gloss, was not an employee of the CIA, according to a person familiar with the matter. His death, which occurred in April 2024, was not considered a national security issue by CIA officials. However, Gloss had previously posted on social media expressing support for Russian troops, and Russian media first reported his death in April. His father, Larry Gloss, an Iraq War veteran, told the Washington Post that he and Gallina were unaware of their son’s whereabouts or his enlistment in the Russian army at the time.

Putin’s move comes at a sensitive time, as Trump has been increasingly frustrated with the Kremlin and has vowed to impose secondary tariffs starting on Friday, even as negotiations are underway for a possible summit. The Order of Lenin, a Soviet-era award, has been given to high-level spies, including the UK’s Kim Philby, a double agent for the Soviet Union.

Witkoff, who left a career in real estate development to become Trump’s envoy for sensitive peace missions, has faced scrutiny for his reliance on Russian government translators during high-stakes diplomacy. However, sources say Witkoff had a U.S. government translator with him during their recent meeting in Moscow, two days before Trump’s deadline for Putin to end the war or face severe financial penalties via sanctions.

Despite Trump’s claims that the meeting was “highly productive,” no sanctions have been issued as of Friday afternoon. Meanwhile, the Trump administration has also imposed an additional 25% tariff on Indian goods, citing New Delhi’s continued purchase of Russian oil.

This incident highlights the complex and often tense relationship between the United States and Russia, as well as the personal toll of the war in Ukraine on families on both sides. With tensions continuing to rise, the coming weeks will be crucial in determining whether diplomacy can prevent further escalation.