Steve Witkoff made his name betting on distressed assets. Now, he is wagering peace in a war zone.
Once a fixture in Manhattan boardrooms, Steve Witkoff—best known for owning the Park Lane Hotel and redeveloping the iconic Woolworth Building—has traded rezoning battles for ceasefire negotiations. And in Donald Trump’s Washington, that unlikely career arc is exactly the point.
After Trump’s return to the Oval Office, Steve Witkoff was tapped as a Middle East envoy. But the role quickly shifted. By spring, he was leading a U.S. diplomatic push in Moscow, working toward a ceasefire in Ukraine. A man who built his empire on luxury hotels now holds closed-door meetings with Vladimir Putin.
But why him? That question has become a quiet obsession among policymakers and power players alike.
Steve Witkoff was born in the Bronx and trained as a real estate attorney before striking out as a developer. In the 1990s, he founded the Witkoff Group, gradually acquiring a portfolio of trophy assets from Miami to Las Vegas. His sons, Zach and Alex, now serve as co-CEOs, continuing the family-run enterprise.
By 2019, the group controlled nearly 50 properties globally. But it wasn’t just buildings that defined Witkoff—it was relationships. Chief among them: Donald J. Trump.
Their bond began decades ago in New York real estate circles and solidified over years of golf games in Palm Beach. In 2024, Steve Witkoff was seen on the fifth hole with Trump during an alleged assassination attempt. Their political alignment is no less visible. Witkoff spoke at last year’s Republican National Convention and has donated generously to the party.
“We are done carrying the financial burden of nations that are unwilling to fund their own progress,” he said during Trump’s inaugural parade. “The days of blank checks are over.”
That worldview—transactional, direct, and unapologetically nationalist—aligns neatly with the administration’s foreign policy.
Over lunch shortly after the election, Steve Witkoff reportedly pitched Trump on a larger diplomatic role, initially eyeing the Middle East. Despite his limited political experience, he quickly became a key figure in backchannel talks between Israel and Hamas. A January ceasefire deal credited to his team led to prisoner exchanges and the partial release of hostages.
Witkoff’s approach, described by diplomats as “empathetic but firm,” has drawn cautious praise. He has openly spoken about the 2011 death of his son Andrew, who died from an OxyContin overdose. In private meetings, sources say, he often references that personal grief when discussing civilian casualties.
But his new role has not been without criticism.
After Trump bypassed Secretary of State Marco Rubio and military advisor Keith Kellogg, sending Steve Witkoff to Moscow, the real estate mogul met Putin twice. Their most recent meeting lasted over three hours, without any official documentation of what was discussed.
Shortly after, Witkoff publicly claimed that Ukraine was viewed by the Kremlin as a “false country” and implied that lasting peace would require Kyiv to concede five contested regions. The backlash was swift.
“Is he an envoy for Trump or for Putin?” asked Oleskandr Merezkho, chair of Ukraine’s foreign affairs committee. Others echoed the concern, demanding he step down.
Further complicating matters, Witkoff has publicly supported Trump’s proposal to “develop” the Gaza region into the “Riviera of the Middle East”—an idea critics say amounts to ethnic cleansing.
Steve Witkoff represents more than a diplomatic experiment. He is a vessel for the Trump administration’s broader realignment of foreign policy: deals over diplomacy, business instincts over bureaucratic norms.
He is not the first real estate developer to dabble in geopolitics. But he may be the only one brokering peace while still managing a luxury portfolio.
Whether his backchannel dealings bring resolution or more confusion remains to be seen. But in an administration where loyalty is currency, Witkoff is rich.
And for now, Trump’s most unconventional envoy holds a front-row seat at one of the world’s most dangerous negotiations.
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