Real-Estate Mogul Steve Witkoff Is Trump’s Point Man on Ukraine

President Trump‘s Middle East envoy, Steve Witkoff, is the congenial dealmaker for the very brash dealmaker-in-chief.

• Witkoff has an expanding portfolio that now includes Trump’s biggest geopolitical challenge — negotiating a deal to end the war between Russia and Ukraine as part of a controversial reset of U.S. foreign policy.

Why it matters: Trump’s cage-rattling agenda — which has shocked European allies — is a keystone of his second term. He’ll rely heavily on Witkoff, a billionaire real estate investor and friend for 40 years, to make it happen.

Zoom in: Associates describe Witkoff, 67, as something of a velvet glove when it comes to negotiating — smooth and to the point.

• Witkoff helped persuade Russian President Vladimir Putin to release U.S. teacher Marc Fogel on Monday, after talks in Moscow.
• Witkoff played a key role in getting Israeli Prime Minister Benjamin Netanyahu to accept a ceasefire-and-hostages deal with Hamas last month.
• He’s also Trump’s point man for talks the president wants to have with Iran to try to reach a new nuclear deal later this year, U.S. officials say.

Trump aides emphasize that Witkoff shouldn’t be seen as overshadowing Secretary of State Marco Rubio. Witkoff was instrumental in advising Trump to pick Rubio, Vice President Vance and White House national security adviser Mike Waltz for their positions.

• They’ve all worked with Witkoff on the Middle East. But a senior Arab official said it’s clear to everyone in the region that Witkoff is Trump’s ultimate representative — and that if you want to cut a deal, you do it with him.

Between the lines: Witkoff’s negotiating tactics are rooted in his experience as a New York real estate mogul, according to those who know him.

• They say Witkoff knows when to employ charm, which he prefers, and when to apply pressure that can channel Trump’s intimidating demeanor.
• “The president sees Steve as one of the world’s great dealmakers,” said one White House official. “Game respects game.”
• “He’s very respectful and direct,” said one official who’s seen Witkoff work. “He doesn’t apologize for the president or undercut him. You never hear him say: ‘Oh, I agree with you and disagree with Trump.'”
• “He has all the good of Trump but he does not need the limelight,” the official said. “He does not need to fly like Icarus, too close to the sun.”

Israeli officials who worked with Witkoff on the Gaza ceasefire deal described him as energetic and informal. Witkoff even came to some negotiation sessions in Doha wearing sweatpants, a sweatshirt and sneakers.

• Witkoff’s energy “was a key factor that led to the deal,” an Israeli official said.

Witkoff favors swift, direct and to-the-point talks.

• “He wants to talk to people that are empowered to close a deal, and not waste his time on talking to people that need to go back to their boss every two minutes to get approval,” a source close to Witkoff said.

Reality check: Israeli and Arab officials told Axios that Witkoff still needs to become more knowledgeable about the Middle East — the different players and the historical and emotional sensitivities that underpin conflicts there.

• Concerns about the U.S. trying to impose a shortsighted policy in Gaza have heightened amid Trump’s call for Palestinians to be removed from war-torn Gaza and relocated permanently to Jordan and Egypt — a plan few see as remotely workable.

Trump’s team faces a significant challenge in talks with Putin over Ukraine. During his invasions of Ukrainian lands in the past decade, Putin has shown no willingness to compromise.

• But much to the consternation of America’s European allies, Trump’s administration has indicated the U.S. is willing to allow Russia to keep some of the territory it has gained.

Flashback: Witkoff was a behind-the-scenes negotiator and fixer during Trump’s 2024 campaign.

• He organized a bury-the-hatchet meeting between Trump and his bitter GOP primary rival, Florida Gov. Ron DeSantis.
• After Trump savaged popular Georgia Gov. Brian Kemp (R) for rejecting Trump’s claim that the 2020 election was stolen, it was Witkoff who met with Kemp to smooth things over.
• Witkoff flew to Kiawah Island, S.C., for a secret meeting with another primary rival, former UN Ambassador Nikki Haley.
• Witkoff was in the room when Trump had his reconciliation meeting with Netanyahu at Mar-a-Lago last July. He was also present when Trump met the Emirati and Qatari leaders in September.

The Trump-Witkoff relationship dates to the mid-1980s, when Trump was a rising New York builder and Witkoff was a real estate lawyer.

• The two became golf buddies and dinner companions. Trump came to appreciate that, unlike others in Trumpworld, Witkoff wasn’t seeking fame.
• And unlike many other longtime friends of Trump’s, Witkoff didn’t ditch him after the Jan. 6 Capitol riot. That resonated with Trump.

“Steve has stayed loyal and asked for nothing,” an administration official said.

• Trump often used Witkoff’s Gulfstream G6 jet during the campaign, including when the Secret Service feared that Trump’s jet would be targeted by Iranian assassins. Vance took a secret flight on Witkoff’s plane to meet with Trump just before his selection as the VP nominee.
• Witkoff also flew to Israel and Qatar for the negotiations that produced the Gaza deal. He gave Joe Biden’s Middle East adviser, Brett McGurk, a ride back to Washington after they sealed the deal.
• Last week, Witkoff’s jet flew to Russia to bring back Fogel, who’d been held there since 2021 for carrying a small amount of marijuana into the country.

Source: Axios