By Jennifer Hansler, Alayna Treene, Kylie Atwood, CNN

(CNN) — As the Trump administration rushes to secure a peace deal to end the war in Ukraine, President Donald Trump is dispatching two of his highest profile diplomats to Moscow.

They are his former business associate and his son-in-law – and neither has been confirmed by lawmakers in the Senate.

Special Envoy Steve Witkoff and Jared Kushner will meet with Russian President Vladimir Putin on Tuesday. The two men will work to get the Russian leader who started the war by invading his neighbor to agree to end it.

Trump’s latest efforts on Ukraine, with face-to-face engagements led by Witkoff, Kushner, Army Secretary Dan Driscoll, and Secretary of State Marco Rubio, underscore his unconventional – and at times controversial – approach to diplomacy.

Throughout his second term, Trump has turned to a tight circle of business associates and trusted allies to try to solve some of the world’s most intractable conflicts.

They have had successes. Witkoff and Kushner were key brokers in the ceasefire agreement reached between Israel and Hamas, which administration officials say is why they’ve been placed at the center of the negotiations to end the conflict between Russia and Ukraine.

After the ceasefire agreement, Trump described Witkoff as being “a great negotiator, because he’s a great guy.”

Witkoff was initially appointed to be special envoy for the Middle East, tasked with trying to bring an end to the war in Gaza. But his portfolio quickly grew to include efforts to end Russia’s war in Ukraine, as well.

His appointment to deal with two of the world’s most complicated crises raised eyebrows in Washington and abroad.

However, a former senior State Department official noted that Trump “has always been reluctant to hand himself over to bureaucracies” and has instead relied on “personal diplomacy.”

The official noted that Trump is not the first president to do this, but that it hearkens back to the pre-Cold War era before the creation of the National Security Council or the professionalization of the foreign and civil services.

Witkoff’s warm relationship with Moscow has stirred concern among some allies, particularly given Witkoff’s history of engaging with top Russian officials without the presence of experienced diplomats – or even, at times, US notetakers.

Trump himself recounted that a meeting between Putin and his special envoy, which was initially expected to last 15 or 20 minutes, ended up stretching some five hours.

“I said, ‘What the hell were you talking about for five hours? And he says, ‘just a lot of interesting things,’” Trump recalled in remarks in October.

In a mid-October call, an audio recording of which was reviewed and transcribed by Bloomberg, Witkoff counseled top Russian foreign policy adviser Yuri Ushakov on how Putin should approach a conversation with Trump – one that took place just a day before Trump met with Ukrainian President Volodymyr Zelensky.

Some European officials said they found the revelation galling, but not surprising. Trump, meanwhile, dismissed concerns.

“He’s gotta sell this to Ukraine, he’s gotta sell Ukraine to Russia. That’s what a deal maker does,” Trump told reporters last week.

Asked Monday about what the Trump expects from the upcoming meeting in Moscow, White House press secretary Karoline Leavitt described the administration as “very optimistic.”

“We’ve put points on paper,” she said during a press briefing. “Those points have been very much refined. But as for the details, I will let the negotiators negotiate. But we do feel quite good, and we’re hopeful that this war can finally come to an end.”

White House national security spokeswoman Anna Kelly said in a statement, “President Trump is proud of the work of his entire national security team, including Special Envoy Witkoff and Mr. Kushner, in speaking with both sides of this conflict to craft a deal that will ensure a durable, enforceable peace.”

Kushner emerges as key figure

Joining Witkoff trying to sell a deal will be Kushner.

Kushner, who has sat in the US delegation for two high-level meetings in as many weeks with Ukrainian officials, has re-emerged as a key figure in the administration’s diplomatic efforts.

Kushner does not have an official US government role. He came back into the public eye as he and Witkoff negotiated a ceasefire plan for Gaza.

On the heels of that tenuous truce, he has been quietly working alongside the businessman-turned-envoy on efforts to end the war in Ukraine, multiple sources familiar with his role tell CNN.

White House officials and people close to Kushner argue there wasn’t a specific point at which it was decided that the president’s son-in-law would begin working on Russia-Ukraine matters. Instead, they argued it was a natural progression of the work he has been doing since even before Trump took office, when he helped advise some administration officials during the presidential transition process on matters pertaining to the Middle East.

Kushner, sources said, is seen by Trump to be his “closer” on foreign policy deals. One source close to him described him as having good ideas on how to get things unstuck.

Sources close to him also argue he has a rare quality that few people even at the highest echelons of the president’s circle don’t possess: Trump’s full trust.

That trust, the sources argued, has been crucial to signaling to foreign leaders that when he is involved, they are essentially dealing with Trump directly.

But there are dangers to relying on such a small circle, as Trump has, the former senior State Department official said.

“You make mistakes, and you don’t have a wide enough circle to challenge thinking, to present opposite points of view,” they said. “You can run yourself down a fairly narrow alley without understanding what the alternatives might have been.”

Trump “believes that his emissaries, whoever they might be, if they’re seen as being directly connected to him and articulating his viewpoint, then that’s what’s important,” the official told CNN.

When it comes to Russia-Ukraine negotiations, “this is the President turning to people that he knows well, that he trusts, he has a level of confidence, and he believes have been successful in other lines of business, and can certainly be successful on this.”

Trump’s “drone guy,” Army Secretary Dan Driscoll, has also emerged as a key figure in the renewed negotiations to end the war, though he is not due to head to Moscow.

Driscoll, a friend of Vice President JD Vance, has held a series of meetings with top Ukrainian officials in Kyiv and Geneva as the administration has pushed them to accept a deal to end the war. He also met with Russian officials in Abu Dhabi.

Leslie Shedd, a former senior adviser on the House Foreign Affairs Committee who now serves as a nonresident fellow at the Atlantic Council, noted that he has “really become a rising star in the administration.”

Former career diplomat Daniel Fried said that “having Driscoll there” as “somebody who is trusted in Trump World is important.”

However, “you need somebody with Driscoll who understands the details,” said Fried, who was US ambassador to Poland. “The Russians can be expected to throw various curveballs disguised as sweeteners. You need somebody who can detect the stink bombs in the nice wrapping.”

Closing a deal

Kushner’s presence on the team working on Ukraine seemed to reflect Trump’s growing frustration over his inability to quickly bring the years-long conflict to end and his desire to translate his approach during the Gaza deal to Russia-Ukraine.

To the Ukrainians, it also signaled that Trump believed that a deal was within reach.

“The Ukrainians think that Trump views Kushner as the closer. They hope that Jared can close the gap, they are working with the administration on this, but they don’t think it is on the finish line,” said a source close to the Ukrainians.

However, some have raised questions about Kushner’s role in the negotiation process as the administration works to broker a deal with a Russian government that even Trump himself has said does not seem to want peace.

One European official noted that it’s “not clear what is his mandate or boundaries.”

“I’ve heard that he’s a very quick learner, but one would expect a member of the negotiating team to have deep knowledge of the issues ahead of attending the meeting rather than learning on the job,” they said. “Obviously it’s quite extraordinary to have someone with no official position as a member of the negotiating team.”

In late October, Witkoff and Kushner met with sanctioned Russian businessman Kirill Dmitriev met in Miami, a source familiar with the meeting told CNN. Dmitriev, like Kushner and Witkoff, is not a conventional diplomat but has close ties to Putin and therefore is viewed as a viable intermediary.

Kushner and Dmitriev, a graduate of Harvard Business School, have reportedly known each other for years. The two men worked together during the first Trump term, one source close to the White House said.

What emerged weeks after that meeting was a 28-point draft denounced by European officials and members of Congress as a capitulation to Russia.

The White House said the draft had been worked on by both Witkoff and Rubio. It underwent changes during a meeting in Geneva between top US and Ukrainian officials in late November, Rubio said at the time. There was continued progress in the discussions in Florida, the top US diplomat said Sunday. Rubio led the delegation at both of those meetings.

“This is delicate, it’s complicated, there are a lot of moving parts, and obviously there’s another party involved here that’ll have to be a part of the equation – and that’ll continue later this week when Mr. Witkoff travels to Moscow,” Rubio said Sunday.

CNN’s Zachary Cohen contributed to this report.

This story has been updated with additional details.

The-CNN-Wire
™ & © 2025 Cable News Network, Inc., a Warner Bros. Discovery Company. All rights reserved.