Special Presidential Envoy Keith Kellogg said Monday that he and the chairman of the Joint Chiefs of Staff recently advised President Trump that Russia is losing its war in Ukraine, citing staggering casualties and minimal territorial gains.
Speaking at the Yalta European Strategy Conference in Kyiv, Kellogg revealed that he and Air Force Gen. Dan Caine, the current Joint Chiefs chairman, assured the president roughly six weeks ago—just prior to Trump’s meeting with Russian President Vladimir Putin in Alaska—that Moscow’s position in Ukraine is deteriorating.
“If Putin thinks Russia is winning, then we have very different definitions of ‘winning,’” Kellogg said. “If he was truly winning, he’d be in Kyiv. He’d be west of the Dnipro. He’d be in Odessa. He’d have changed the Ukrainian government. None of that has happened.”
According to Kellogg, the two senior military officials offered their assessment after Trump questioned reports of Russian success in Ukraine. Kellogg recounted encouraging the president to hear directly from Caine.
“I said, ‘Mr. President, don’t just take my word. Your chairman of the Joint Chiefs is right outside. Bring him in,’” Kellogg recalled. “And when he did, Dan said the same thing: ‘Nope, not winning.’”
Kellogg said Russia has suffered over one million casualties since launching its full-scale invasion in 2022, while managing to seize less than 1% of Ukrainian territory since November 2022. He added that despite some recent gains in the Donetsk region, those advances are minimal and come at an extraordinary cost.
“They may be moving in the Donbas, but we’re talking meters, not miles,” Kellogg said. “The losses they’re taking are enormous, and I don’t think people truly understand the scale.”
Drawing historical comparisons, Kellogg noted that the Soviet Union withdrew from Afghanistan after 18,000 casualties — a stark contrast to Russia’s current losses, which he described as “World War II-level numbers.”
“They’re pulling tanks out of storage, even museums, just to put them on the front lines,” he added. “They can’t conduct large-scale operations because Ukrainian forces will destroy them. And the Ukrainians are fighting bravely.”
Kellogg also sought to dispel the myth of Russian military dominance, telling officials in a recent Oval Office meeting not to overestimate Putin’s capabilities.
“They were talking about the strength of the Russian military,” he said. “And I told them, ‘We’d kick their ass.’ By that I mean: don’t buy into the hype. They’re not as capable as Putin claims.”
He emphasized that the West should not be intimidated by Russia’s military rhetoric, calling on the U.S. and its allies—particularly in Europe—to increase pressure on the Kremlin.
“This is a nuclear power, yes,” Kellogg said. “But I don’t believe they have the military capacity to threaten places like Berlin anymore. The fear is overstated.”
Kellogg urged European nations to take tougher economic measures against Russia, especially by ending purchases of Russian oil—a position Trump has also strongly advocated.
“You need to raise your risk level,” he told Western partners. “Apply real economic pressure. Make the hard calls. Shut down their oil revenue. It’s a petrostate, and that’s how they fund this war.”
He concluded by praising Ukrainian forces for significantly weakening Moscow’s military.
“The Ukrainians have knocked them down several notches,” Kellogg said. “Nobody should be afraid of the Russian military anymore.”