Trump Envoys' 'Ludicrous' Russia Mistake Shocks Expert

A retired Army general looked at how two of President Donald Trump's envoys reached their meeting with Vladimir Putin and could not get past one detail. They let a Russian government vehicle drive them there.

Retired Army Maj. Gen. Randy Manner told CNN's Erin Burnett on "OutFront" that Steve Witkoff and Jared Kushner made a "ludicrous" mistake by taking that ride on Saturday in Moscow. The two men were there to talk with the Russian president about ending the war in Ukraine. Manner's issue was not the flattery or the closed doors. It was the car.

He said those vehicles can carry gear that pulls data straight off a phone. Get close enough, Manner said, and "they can take everything off of your phone and copy it without you even knowing it." Every contact, message and email could, in his words, "then belong to the Russians." He called the decision proof of "the ignorance and lack of knowledge in general about how sophisticated the Russians are."

Trump sent two real estate guys to face Putin

Neither envoy came up through the State Department or the military. Witkoff and Kushner are real estate developers. Kushner is Trump's son-in-law and served as a senior adviser during the president's first term. Witkoff holds the title of special envoy to the Middle East, and Kushner helped put together the 2020 Abraham Accords, the deal that saw several Muslim-majority countries recognize Israel.

Trump has handed both men his hardest assignments anyway. He called the pair "great negotiators" and said they were carrying "a proposal to end the war" when he sent them off. The complaint from critics keeps circling back to the same thing. These are men known for building towers and closing property deals, not for arms control or the kind of intelligence work a trip inside the Kremlin demands.

Their eighth trip, and a warm word for the man across the table

Saturday marked Witkoff and Kushner's eighth visit to Russia, Kremlin aide Yuri Ushakov said, and their second this year. On camera, Witkoff struck a friendly tone with Putin that landed badly in Kyiv. He thanked the Russian leader for hosting them, then drifted into talk about the future.

"We'll have all these incredible stories and incredible memories, and yours will be right at the top of it all," Witkoff told Putin in remarks recorded during the visit. Putin thanked Trump for pushing to end a war he called "not simple" and promised to protect the envoys as they traveled on to Ukraine. Alexey Muraviev, an associate professor of national security and strategic studies at Curtin University in Australia, said the view inside Ukraine is that Witkoff, and to some degree Kushner, are the most likely to accept Russia's version of events.

More than three hours behind Kremlin doors

The Moscow meeting ran more than three hours inside the Kremlin's Red Drawing Room and ended with no announced breakthrough. It was the pair's first Moscow trip since January, after months in which the administration's attention had shifted to the war with Iran.

Kremlin aide Yuri Ushakov called the talks "highly useful" and said the Americans "outlined a number of ideas regarding possible avenues for a settlement," without offering details. He described the conversation as "substantive, very frank and constructive." It reached past the battlefield and into possible joint business ventures between Russia and the United States, which tells you something about the room those two were sitting in.

Kyiv finally got a visit

On Sunday the envoys took a train from Poland into Kyiv, their first stop in the capital since Russia's full-scale invasion in February 2022. Volodymyr Zelenskyy met them in the city center. "It is very important that the delegation has arrived to see us. We have been waiting a long time for Steve and Jared, Witkoff and Kushner," he said, thanking Trump for allowing them to come.

Witkoff called the discussion "very meaningful, substantive, important" and said he was "very encouraged." Kushner said Trump wanted "not just to figure out how we end the current war, but how do we create the right conditions and arrangements for a long-term, durable peace." Zelenskyy took the two to Saint Sophia's Cathedral, which sits across from a Security Service building that a Russian drone had hit on Friday. British, French and German national security advisers joined a later round of talks.

Not everyone thinks these are the right guys

Manner was not the only military voice picking the trip apart. On a CNN panel hosted by Audie Cornish, Harrison Mann, a former U.S. Army major and former executive officer at the Defense Intelligence Agency, said the choice of envoys itself was the tell. "You don't send Kushner and Witkoff when you actually really want to get something done," Mann said on the panel.

He pointed to who was missing. "You can notice Vance and Rubio are nowhere near this right now, which gives you an idea of the lack of seriousness, in my view," Mann said. He also argued the American position had gotten weaker since the last round in February. "Trump started this big war in Iran. And that's probably the biggest effect that has weakened the negotiating position of Ukraine and the pro-Ukraine alliance," he said. His verdict on the job in front of the two envoys was blunt: it is "up to, apparently, Witkoff and Kushner to bridge this gap, which I don't really think that they're qualified to do."

What the fight is actually about

The gap is real, and it is drawn on a map. In September 2022, Putin proclaimed the annexation of four partially occupied Ukrainian regions: Donetsk, Luhansk, Kherson and Zaporizhzhia. The international community, including the United Nations, never recognized the move. Moscow now wants Ukraine to stay out of NATO and hand over territory, including land its forces do not even hold. Kyiv has refused to cede ground.

Mann laid out the two biggest sticking points. Russia captured the Zaporizhzhia nuclear power plant, and Putin is demanding that Ukraine give up even more of the Eastern Donbas in exchange for peace. Zelenskyy has said the toughest questions, like territory, can only be settled at the level of national leaders. He also insists any deal include hard security guarantees and a "dignified post-war peace."

The bombs came back on Tuesday

Both capitals had agreed to a three-day halt on strikes to cover the envoys' travel. That window closed fast. On Tuesday morning, Russia pounded Kyiv with ballistic and cruise missiles and drones for nearly five hours. Five people were killed and about 35 wounded. Ukrainian Interior Minister Ivan Vyhivskyi said the assault ran nearly five hours.

Zelenskyy called the assault "complex" and said it was built to cause as much harm to life as possible. Rescuers pulled people from a five-story residential block in the Solomyanskyi district. A drone also struck a passenger train running between Kyiv and Sumy, though its 90 passengers and crew got off first. "Everything was thundering on the left bank," Iryna Barisenkova, 61, said. "It was just brutal." That is the backdrop the two real estate developers are working against, a day after they left town promising progress.