It was 1986: Greed was good and the hours were punishing. Still, even round-the-clock dealmakers had to eat. That is how Donald Trump happened upon Steve Witkoff at a deli counter in midtown Manhattan at 3am. One was a son of Queens, the other of the Bronx. Both were hungry. Mr Witkoff paid.
Forged over a ham-and-cheese sandwich, their friendship has thrown Mr Witkoff into the eddy of geopolitics. In November Mr Trump named him envoy to the Middle East. When a senator reacted with surprise—Mr Witkoff had zero prior diplomatic experience—Mr Trump reportedly replied: “Well, a million people have tried. Let’s pick a nice guy who’s a smart guy.” Mr Witkoff, still full of vim, has embraced the job. In just a few weeks his diplomacy has brought him to Doha, Gaza, Jerusalem, Moscow and Riyadh.
Mr Witkoff’s first order of business, before his boss had even been inaugurated, was to negotiate a ceasefire between Israel and Hamas. When he told aides to Binyamin Netanyahu that he would arrive in Israel on a Saturday for talks, they said that the prime minister was observing the Sabbath, but that he would be available after sundown. Not good enough, replied Mr Witkoff, who is also Jewish. Mr Netanyahu obliged, and a truce was agreed. Brett McGurk, who worked on the deal for the outgoing Biden administration, said he and Mr Witkoff developed a “close partnership, even friendship”.
Ceasefire in hand, Mr Witkoff broadened his portfolio. In February he flew to meet Vladimir Putin and secure the release of Marc Fogel, an American prisoner held in Russia. He and the Russian president met for three and a half hours; Mr Witkoff called it “trust-building”. Notably absent was Keith Kellogg, Mr Trump’s envoy to Ukraine. Back at the White House, Mr Fogel praised the “can-do attitude [that] just exudes from his body”.
Diplomats with such a challenging brief tend to have oodles of experience handling foreign leaders and matters of national security. Mr Witkoff has neither. Like his boss, he is a billionaire property developer who made his career in New York City and south Florida. But he has what counts in this White House: a dealmaker’s savvy, a penchant for flattery and a fortune. Mr Witkoff spent nearly $2m to help elect Mr Trump. His grandson is named after the president. His son Zach is a co-founder of the president’s crypto platform, World Liberty Financial.
He also has Mr Trump’s trust. They have seen each other lose—or almost lose—everything. When one of Mr Witkoff’s sons died of an opioid overdose, Mr Trump grieved alongside him. Mr Witkoff was at Mr Trump’s side when a man tried to assassinate him on his golf course in September.
Their rapport stems from the fact that both are outer-borough strivers who began in down-market property, then made it in Manhattan luxury developments. Mr Witkoff got his start at 29 by buying apartment buildings out of foreclosure in seedy parts of the city. He would sometimes fix plumbing problems himself; he occasionally carried a gun. “I had a lot of scares,” he later recalled.
Those days are long gone. Mr Witkoff owes his success to his amiability and vision. When others had lost faith in downtown Manhattan, he bet on its revival. “We just thought that New York City would always rise and the market was just too cheap down there not to take advantage of it,” he once explained. A good developer, he has said, is cautious and prudent—but also a believer. More recently his property empire has included the Park Lane Hotel on Central Park South, known as billionaire’s row. In 2023 he sold that trophy to the Qatari sovereign-wealth fund for $623m.
Such dealings with a foreign government would normally be considered a disqualifying conflict for any diplomatic job. To Mr Trump it is an asset. What this actually means for Gazans and Ukrainians does not look good. Before the blow-up between Mr Trump and Volodymyr Zelensky at the White House, it seemed like Ukraine would hand over large parts of its mineral wealth to America. Meanwhile, Mr Trump is eying Gaza with a developer’s yen. The president’s suggestion to wholly relocate Gazans—at once callous and dismissive—appears to have been partly inspired by Mr Witkoff, who told him the territory is simply uninhabitable.
Mr Witkoff’s brief time overseeing the Israel-Gaza portfolio captures the potential and the peril in his appointment. Energy and fresh thinking ought to come in handy for seemingly intractable problems; already he has delivered successes. But in the long run, the transactional diplomacy of the Trump administration is more likely to weaken America’s interests than strengthen them. ■