Army Secretary Dan Driscoll was at the White House earlier this month preparing for a trip to Kyiv to discuss drone technology when he received an unexpected assignment from President Donald Trump: push Ukraine to come back to the table for peace talks with the Russia — and do it fast.
The 38-year-old Army veteran and close friend of Vice President JD Vance, his classmate at Yale Law School, had no prior diplomatic experience. But an “Army-to-Army” discussion seemed promising, said one person familiar with the discussions: The Ukrainians know and trust US Army officials, who have trained and equipped their forces for more than a decade.
Trump also likes Driscoll and refers to him as the “drone guy,” people familiar with their dynamic said, a nod to Driscoll’s extensive work on developing new drone technology for the Army. And Trump asks Driscoll for his opinion on “what to do about Ukraine” whenever he is at the White House, one of the people said.
Driscoll was excited to take on the challenge, one of the sources said. And after a weeklong diplomatic blitz across three countries, he appears poised to return home with a partial victory: Kyiv has agreed to the “key terms” of a peace agreement that he and Secretary of State Marco Rubio workshopped with Ukrainian officials in Geneva over the weekend.
Driscoll’s involvement exemplifies Trump’s unconventional approach to international crises, tasking figures with whom he has business or personal ties to lead US negotiations rather than career diplomats. The president’s son-in-law Jared Kushner has long been crucial to his efforts in the Middle East, and he appointed his longtime business associate Steve Witkoff as his special envoy focusing on the conflicts in Ukraine and Gaza.
The person familiar with the dynamic said Driscoll was communicating with the White House every step of the way, with Trump issuing directives through Vance and Witkoff.
“It was all happening so fast, and the only way to do that is with this extreme trust that these guys have with each other,” this person said of the relationship between Driscoll, Vance and Witkoff.
The Russians, whom Driscoll met with on Monday and Tuesday in Abu Dhabi, have not yet signed off on the plan, which was amended significantly from the US’ original 28-point proposal that appeared heavily weighted toward Moscow’s interests.
But Driscoll’s high-stakes assignment underscores his elevated status within the administration, sources told CNN, something he has not shied away from despite the fact that his proximity to the White House and to Vance has previously caused tension with Secretary of Defense Pete Hegseth.
Driscoll has “really become a rising star in the administration,” said Leslie Shedd, a former senior adviser on the House Foreign Affairs Committee who now serves as a nonresident fellow at the Atlantic Council.
Trump “is bringing in all of his all-stars off the bench to see who can get the best deal, who’s going to be able to have the best impact,” she said. “You don’t want to keep sending people back over and over again if you feel like there’s been a long-jam negotiation.”
Notably, however, Hegseth has not been one of those “all-stars” called off the bench. Driscoll’s unusual role has also revived speculation that he could ultimately replace Hegseth as secretary of defense, something administration officials have quietly discussed for months, CNN has reported.
His assignment has resulted in a striking split screen with Hegseth, optics that have not gone unnoticed in the secretary’s office, one source said. As Driscoll was engaged in sensitive diplomacy overseas on issues of war and peace, Hegseth was at home, spearheading an investigation into Democratic Sen. Mark Kelly and posting about it on X. Driscoll has kept Hegseth apprised of his progress in the talks, one of the sources said.
Tasking Driscoll with the diplomacy was also a recognition that Hegseth’s relationship with the Ukrainians soured early on in his tenure, one of the sources said. The Pentagon chief paused US weapons shipments to the country multiple times without informing them — or the White House — first, CNN has reported. Hegseth also prematurely ruled out Ukrainian membership of NATO at one of his first overseas meetings with allies in Brussels earlier this year.
Still, Driscoll is inexperienced in diplomacy — particularly when it comes to dealing with the Russians.
“I think that having Driscoll there, that is somebody who is trusted in Trump world, is important,” said former US Ambassador to Poland Daniel Fried. But “you need somebody with Driscoll who understands the details, because the Russians can be expected to throw various curveballs” that may not seem like curveballs.
“You need somebody who can detect the stink bombs,” Fried added.
CNN’s Jennifer Hansler contributed reporting.
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