Behind an unassuming West Wing office door works a revolutionary figure in American diplomacy – a billionaire real estate investor with no foreign policy background who meets alone with Putin, bypasses Netanyahu, and negotiates directly with Hamas. Steve Witkoff, President Donald Trump's special envoy to the Middle East with expansive authority, carries two Star of David pendants around his neck, one from his late father and one from his son who died of a drug overdose in 2011.
A profile piece in The Atlantic gives new insights into the man and his works, and how the New York tycoon has in just five months orchestrated prisoner exchanges with Russia, brokered hostage releases from Gaza, and pursued both Iranian nuclear accords and peace in Ukraine. His unprecedented diplomatic latitude comes from a 40-year friendship with President Donald Trump and a deal-making philosophy that sees world leaders not as ideological enemies but as potential business partners. "I'm not an ideologue," Witkoff told the magazine with a smile. "Remember, I'm the amateur diplomat."
"Steve Witkoff emptied his backpack on the conference table in his second-floor office, in the West Wing. He wanted to show me a pager given to him by Israeli Prime Minister Benjamin Netanyahu and senior officials of the Mossad. The pager commemorates the intricate operation in which Israel detonated handheld devices used by Hezbollah, the Iranian-sponsored Lebanese militant group, killing or maiming thousands of its operatives," the author of the piece writes. "Witkoff located the gadget amid a tangle of electronics he uses to communicate abroad in his role as America's shadow secretary of state. The back of the pager, he proudly told me, carries an inscription: Dear Steve, friend of the state of Israel. And then the acronym OTJ, for "One Tough Jew."
This toughness is evident in Witkoff's willingness to challenge Netanyahu when American interests demand it, The Atlantic reports. Recently, he worked through back channels to secure Hamas' release of Edan Alexander, the final living American hostage in Gaza – accomplished without Netanyahu's involvement.
Witkoff's meteoric rise has confounded America's professional diplomatic corps. His responsibilities have diminished those of Secretary of State Marco Rubio, who lacks what Witkoff possesses: a 40-year friendship with Trump.
"A person like Donald Trump has many, many, many acquaintances, far too many to even name or count," Susie Wiles, the White House chief of staff, told The Atlantic. "But I think he would say he has very few true friends outside of his family, and Steve has to be first among equals there."
At 68, Witkoff speaks more softly than the president but shares Trump's affinity for bold pronouncements. "We're going to have success in Syria; you're gonna hear about it very quickly. We're going to have success in Libya; you're going to hear it quickly," he told The Atlantic, outlining his ambitious diplomatic agenda.
What distinguishes Witkoff is his complete lack of diplomatic experience. "This is sort of like 'Mr. Smith Goes to the Mideast,'" Senator Lindsey Graham remarked to The Atlantic. Despite his inexperience, Witkoff has shown skepticism in dealing with Israeli officials. To facilitate a January agreement, he reportedly told David Barnea, Mossad's head, that he would need to answer to families whose children might never return from Gaza captivity if Israel rejected the deal.
Around March, US officials initiated direct dialogue with Hamas – breaking with established American protocol. This week's release of Alexander, negotiated with assistance from Bishara Bahbah, chairman of a group formerly called Arab Americans for Trump, completely excluded Israel from the process.
These developments have astounded veteran experts. Aaron David Miller, a former State Department Middle East analyst and negotiator, told The Atlantic that Witkoff "has been empowered to use tools that no administration has ever used." He added, "We've never seen an administration separate itself from Israel like this."
Rather than restraining Israel, Witkoff's approach has been to circumvent Netanyahu to advance Trump's objectives. Israel's recent announcement of intensified warfare in Gaza prompted a shrug from Witkoff. The behavior of Hamas, he told The Atlantic, "has been so poor that Bibi in certain circumstances has felt that he has no alternative." Any lasting resolution, he stated, must involve the "total demilitarization" of Hamas.
Video: Trump arrives in Qatar / Reuters
This breakthrough highlights Israel's failure to free remaining hostages – frustrating Witkoff, who reportedly told hostage families, "Israel is prolonging the war, even though we do not see where further progress can be made." Having Netanyahu's support seems less important to Witkoff than Israeli public backing. He told The Atlantic, "If you look at the public opinion in Israel, it's split more than down the middle on behalf of getting the hostages out and having a negotiated settlement to this thing."
When asked about expectations that Israel would participate in discussions with Hamas, he responded: "I make of it that the president is the president, and I follow his orders."
Witkoff has faced criticism suggesting Qatar's influence over his diplomacy. He rejected these implications, highlighting his pro-Israel credentials: "I was in the tunnels with the head of Southern Command. Does that sound like I'm a Qatari sympathizer? I'm a Krav Maga double black belt. I am no Qatari sympathizer. What I am is a truth teller."
Born in the Bronx and raised on Long Island, Witkoff descended from Eastern European Jews, The Atlantic reports. His father manufactured women's coats while his mother taught third grade. Growing up, he learned Krav Maga, a martial art used in Israeli military training.
Witkoff carries his heritage visibly – during meetings, he displays two Star of David pendants, one from his father and another from his eldest son, who died of a drug overdose in 2011. After Alexander's return from captivity, Witkoff presented him with the necklace once worn by his son.
His team remains extremely compact. "We're like a SWAT team," Witkoff told The Atlantic. He has a deputy, Morgan Ortagus, an experienced national security professional, but otherwise relies on limited staff while accessing intelligence community resources.
Beyond his Israel-Hamas work, Witkoff has met with Putin three times without career diplomats, translators, or note-takers present – Putin's conditions, which Trump approved. He's working on potential peace arrangements for Ukraine and pursuing talks with Iran, where a senior Israeli official expressed doubt about Tehran accepting Washington's terms but offered: "If anyone can reach a deal, it would be Witkoff."
What Witkoff lacks in diplomatic credentials, he compensates for with a dealmaker's perspective. "I'm not an ideologue," Witkoff told The Atlantic. "Remember, I'm the amateur diplomat."
Trump's devotion to Witkoff owes largely to his loyalty after the Capitol riot on January 6, 2021. "Steve was there for him in the worst hours of his life," Thomas J. Barrack Jr., now ambassador to Turkey, told The Atlantic. "In that four-year hiatus, most of the world thought that he was never going to be president again, or maybe never even see the light of day, but Steve stuck with Donald."
