The first time Steve Witkoff spoke to Donald Trump, it was not about Middle East peace or hostages in Gaza. It was about a sandwich. “It was two in the morning in the hallway of a Manhattan law firm,” Witkoff recall when asked about this topic. “I was an associate, exhausted, ordering food. He hears me and says, ‘Would you mind getting me something too?’ Even then, he was a legend. I was startled that he was asking me to order his sandwich.” The order, Witkoff usually laughs, was “probably a ham and cheese,” because the Jewish delis were closed at that hour. What followed, over decades, was a friendship that now frames one of the most sensitive diplomatic assignments on Earth.
Today, Witkoff calls himself an emissary of President Trump. He is a New York real-estate billionaire turned back-channel operator, a man who shuttles between Jerusalem, Doha, Cairo, Riyadh, and Washington, speaking with leaders who rarely admit they speak with one another. He says the job is not about him. “I am not interested in exalting me,” he repeats behind closed doors. “The person to be exalted is Donald Trump.” He’s even allergic to the first-person pronoun in this context: “You’re not going to hear me use the word ‘I.’ I’m really not interested in being part of something that exalts me.”
His official title is United States special envoy to the Middle East and special envoy for Peace Missions, but de facto, he is Trump’s representative for international issues, wherever it may be. In person, Witkoff’s intensity is less bluster than propulsion, an engine tuned to “find another way.” The vocabulary he returns to in his speechs is simple and stubborn: timing, patience, dignity, and results. “The president never quits,” he says. “If one avenue closes, you find another. You keep pushing. That becomes infectious to everyone around him.”
The emissary role, as he tells it, took shape in Palm Beach after the election, in a conversation that drifted from celebration to service. He and Jared Kushner had been discussing potential roles he could play if Trump returned to power. Conflict resolution, he believed, would define the Middle East portfolio. He had the Rolodex. “I wanted to do some good,” he once told a friend. “My skill set [was] set up well for it. I’m a communicator, and I know plenty of people in the Middle East, not just on the Israeli side, but in the Arab world.”
Empathy as method
The most revealing part of Witkoff’s approach is not his proximity to power but his proximity to grief. “I’m a member of a terrible club,” he once told hostage families quietly, “parents who lost a child.” His son Andrew died of an overdose 14 years ago. “I can go to New Montefiore Cemetery and spend time with him. The families without a grave, no shiva, no yahrzeit, no closure, that is an extra burden beyond the burden.” He says the word “closure” the way a negotiator might say “ceasefire”: A goal line.
When former hostage Edan Alexander came home, Witkoff took the Magen David that had hung on Andrew’s chest and placed it around the young man’s neck. Alexander, a 21-year-old Israeli-American, was freed in May during a brief pause in fighting; US officials called the release a narrow opening for harder talks to follow.
The empathy extends well beyond the living. Witkoff has become a fierce advocate for returning the bodies of Israelis murdered on October 7 and afterward. “It’s not just a policy point, it’s a cemetery,” he often says. “It’s parents knowing when to say kaddish; they never had shiva.” He describes conversations with hostage families like the Chen and others, the hole in their hearts compounded by the absence of remains. “Closure, closure is a big deal when you’ve lost a child,” he says. “They need that.”
An elevator with the Mossad chief
Outwardly, Witkoff is a tough businessman, but, as you can understand from this profile, he is actually very sensitive and personable. One of his most indelible memories is set between floors. After the first major hostage release was hammered out through the Doha-Cairo channel, he stepped into an elevator with Mossad director David Barnea. “We cried together,” he revealed once to his close family. “We knew lives were saved.” He phoned Trump. “I said, ‘Mr. President, on your behalf, we secured the release of dozens.’ He said, ‘Job well done.’ I thought: this is a new level with a man I’ve known since a 2 a.m. sandwich.”
He is brutally clear-eyed about the work. He hasn’t been on a vacation since entering his position. His phone rings every day, all day. “Russia. Qatar. Egypt. Israel. You talk to all of them. If there’s miscommunication, you correct it. If the door closes, you try the window.”
Even among Israel’s closest friends, impatience has grown. Witkoff does not pretend otherwise. “When the president says Israel is burning through political capital, we need to discuss it,” he recently said behind closed doors. “There were things that happened that did not need to happen, on both sides.” He is unsparing about Hamas’s choices: “They could have shown a different face, bring the Red Cross, medical care, food to Israeli hostages.” And he is practical about public opinion. “Public relations are a critical part of it. Public opinion is a terrain. You cross it carefully.”
Strip the complexity to first principles, and Witkoff offers a simple test: “Both sides must feel it is good for them.” In practice, that means operating a control panel with dozens of levers, Israeli public opinion, Palestinian public opinion, the health of those still underground, the risks to captives if fighting surges in the wrong place at the wrong hour, the durability of the guarantors, and the optics of every handshake. “Something will always wobble,” he says. “You don’t quit. You find a different avenue.”
For Witkoff, the families supply the moral metric. While meeting with Israeli officials, he likes to recount on a moment with Keith and Aviva Siegel, who were released hostages. Aviva was released in the first ceasefire shortly after October 7; Keith was only released a year later. “He told me the toughest thing would have been if they released him first and not his wife, having to live with that. It was a little bit of a Sophie’s Choice moment,” he says. “You meet people like that, you see a strength that’s hard to describe. The president feels an affinity for people who don’t give up.”
‘He never quits’
Witkoff’s argument is about character. He portrays Trump as a leader who values diplomacy, employing pressure when necessary and restraint when the point is made. “He never quits,” Witkoff said a few weeks ago in a meeting. “He believes diplomacy saves lives.” He adds small, private facts: how often Trump will clear his schedule to see hostage families who show up at the White House without an appointment; how he is, in Witkoff’s phrase, “a real humanitarian,” captivated by the endurance of people who refuse to give up.
“There was a point in an early negotiation,” he constantly says to his small but effective staff, “where the president made it very clear to the other side: It will not be a great day for you if you don’t release. That theme drove the negotiation. That’s how we got people out.”
To Israelis who have stopped believing that everyone will come home, Witkoff recently offered hope, “Do not lose faith,” he says. “We are never going to give up.” He rejects the theater of cynicism that treats setbacks as endings. He’s frank that egos and domestic politics on all sides can make the tunnel feel endless. And he’s unembarrassed to put hope in timing. “Sometimes what feels like a step backward creates the political space to move,” he says. “You have to be patient.”
A necklace, a promise
The most dramatic moment in Witkoff’s life happened was when he took a call from the hospital after Andrew’s death; a voice on the line asked about organ donation. “I wasn’t present,” he has told hostage families. “I had never fainted before. I was in some sort of vortex. Today, I would have donated. Back then, I did not.” The regret lives alongside gratitude. He wears his father’s Star of David from the Yom Kippur War era, and until May, he wore Andrew’s, too. When Edan Alexander came out, Witkoff slipped Andrew’s star over the young man’s head. “I don’t have an organ to give today,” he told himself. “I’m going to give him what my boy wore.”
In his many conversations, he keeps returning to the families who have already been reunited and who still spend their days fighting for those who remain in Gaza. “They’re not on vacation,” he says. “They’re out there advocating, sometimes for people they don’t even know.” He then recalls Keith Siegel again: “He said the toughest thing would have been if he got out before his wife. He wanted her out first. That kind of love, that kind of endurance, the president is impressed by that. He feels an affinity for people who don’t give up.”
Witkoff always insists he’s not the story. He’s a hinge, one of the people you meet when the door opens between rooms that aren’t supposed to connect. But he will allow himself a hope about the ending. “When this ends, I want to stand back and let the families fill the stage,” he says. “I’ll take a private moment to count blessings. And I hope the president gets the recognition he deserves. Many people matter in this story. The most important person is him.”
The sandwich story at the top sounds almost too neat for an era that mistrusts neat stories. But perhaps its shape is instructive: a 2 a.m. hallway, a small request, a kindness that becomes a through-line. A relationship that migrates from food to essence. The scale is different; the verb is the same. Bring. A sandwich then, a person now. “Never give up,” he says. “Find another avenue. Bring them home.”