Russia ‘losing’ war on Ukraine, Joint Staff chairman, envoy tell Trump

Special Presidential Envoy Keith Kellogg on Monday said he and the chairman of the Joint Chiefs of Staff recently advised President Trump that Russia is losing its war on Ukraine — as Moscow has seen more than 1 million casualties while taking less than 1% of Ukrainian territory since November 2022.

Speaking at the Yalta European Security Conference in Kyiv, Kellogg revealed he and the chairman, Air Force Gen. Dan Caine, each reassured the president of Moscow’s wilting position roughly six weeks ago — shortly before Trump’s meeting with Russian President Vladimir Putin in Alaska.

“If Putin thinks Russia is winning, his definition of winning and my definition of winning are absolutely two different things,” Kellogg said. “If he was winning, he’d be in Kyiv. If he’s winning, he’d be west of the Dnipro River. If he was winning, he’d be on Odessa. If he was winning, he would have changed the government.

“Russia is, in fact, losing this war,” he added.

The two military experts gave their assessment in response to Trump’s then-prodding as to whether Putin’s grandstanding of supposed success in Ukraine was true, Kellogg said, giving a rare glimpse into private discussions at the White House.

“I responded quite forcefully, and I finally said, ‘Mr. President, don’t just listen to me. Your chairman of the Joint Chiefs, Dan Caine, is outside. He’s out in the hall, bring him in and ask him that question. He’s your senior, he’s your principal military adviser,’” Kellogg said.

“And he did, and Dan said the same thing. He went, ‘Nope, not winning.’”

The envoy said he also told leaders during a recent discussion in the Oval Office not to believe Putin’s claims of having a formidable fighting force, reassuring senior administration officials they should not be afraid of Russian retaliation against the US — something that held former President Joe Biden back from taking stronger action against Moscow.

“They were talking about the primacy of the Russian military and how they were, you know, pretty good,” Kellogg said. “And I said to the people in the room, ‘We’d kick their ass.’

“And what I mean by that is: Don’t take their statements at face value. They’re, I mean, they’re not as good as Putin says they are.”

Still, Kellogg acknowledged that Moscow has made some minor territorial advancements in Ukraine’s east — but he said its losses far outweigh any gains.

“They may make movements. It seems so they’re advancing in the Donbas region, in the Donetsk, but if you consider advancing moving by meters, not miles, well then OK, that’s successful, but the cost that they’re having is enormous, and I don’t think people truly appreciate it,” he said.

Manpower-wise, the cost to Russia has been “well over a million” when considering the total troops dead and wounded, he said, noting that the Soviet Union left Afghanistan after losing 18,000.

“These numbers are World War II-level numbers, when you think about it. They’re stunning in the loss,” he said. “… They’re pulling tanks out of mothballs, out of museums, to put on the battle line. They can’t operate in large movements because the Ukrainians will kill them. And Ukrainians are fighting valiantly on there.”

“So do I think the Russians are winning? Putin says it, and I think the West just needs to push back and say, ‘No, you’re not.’”

Kellogg credited the Ukrainian military for taking Moscow’s forces “down a couple of notches,” noting that no one “should be afraid of the Russian military.”

“It’s a nuclear power, check that box — I’ve got that. But I don’t believe they’ve got the capacity that they had that they could march towards Berlin or anywhere else,” he said.

Kellogg also told western partners to “raise [their] risk level” when dealing with Putin, calling on Europeans to take more decisive action against Moscow — including by stopping purchases of Russian oil, which Trump has said is the main source of income fueling the Kremlin’s war machine.

“You’ve got to apply absolute economic pressures, and this means you got to put some risk into the game,” he said. “You’re gonna have to make a hard call … and when you talk about the oil, shut down their revenue. It’s a petrol state.”