Were a list of the most improbable architects of modern diplomacy to be drawn up, then Steve Witkoff would stand out by a mile. A New York real estate magnate turned U.S. special envoy, he now finds himself at the heart of two of the world’s most intractable conflicts of our time - negotiating ceasefires and hostage releases in Gaza while attempting to broker peace between Ukraine and Russia after three years of bitter strife. For a man who once built skyscrapers, the scale of his current task is daunting.
Witkoff’s name may not carry the same diplomatic heft as Henry Kissinger or Richard Holbrooke, but his rise is strikingly reminiscent of the businessman-as-diplomat archetype America has occasionally favoured. Like Thomas Jefferson’s reliance on merchant-turned-negotiator John Jay or Donald Trump’s fondness for Jared Kushner’s real estate-driven problem-solving, Witkoff represents the latest chapter in a tradition where hard-knuckled deal-making is likened to statecraft.
Born and raised in the Bronx, Witkoff built a fortune developing high-end properties, cultivating a reputation as a shrewd businessman with a nose for undervalued assets. His relationship with Trump spans decades, forged on golf courses and in Manhattan boardrooms. That connection propelled him to his current role as special envoy, tasked with untangling the geopolitical thickets of war and diplomacy.
He has been at his task with all the chutzpah of a hotshot property tycoon. History offers several precedents for Trump’s reliance on nontraditional envoys. The most obvious is Henry Kissinger, who, despite being a scholar, was initially dismissed by foreign policy elites for his lack of traditional diplomatic credentials. Kissinger revolutionized American diplomacy through backchannel negotiations, particularly with China and the Soviet Union, relying on secrecy and high-pressure dealmaking. However, Kissinger was a trained strategist with a deep understanding of history - qualities Witkoff has yet to demonstrate.
As the administration’s Middle East envoy, Witkoff has been tasked with navigating Trump’s hardline stance on Hamas. When Trump issued an ultimatum demanding the immediate release of hostages or destruction of the group, Witkoff stood by his side, oscillating between bellicose rhetoric and cautious diplomacy.
Kissinger once remarked that diplomacy is the art of restraining power, whereas Trump’s philosophy appears to be about maximizing it. This difference in worldview is evident in Witkoff’s approach. Unlike traditional envoys, who balance pressure with incentives, Witkoff has so far relied on unilateral ultimatums.
Witkoff’s approach mirrors that of Trump’s broader foreign policy - muscular, unpredictable and often dismissive of traditional diplomatic protocols. Unlike previous envoys who sought multilateral solutions, he operates with the ethos of a private dealmaker, seeing negotiations as transactional rather than strategic.
His handling of Israeli Prime Minister Benjamin Netanyahu revealed both his strengths and weaknesses as a negotiator. When Netanyahu initially delayed ceasefire negotiations, citing religious observance, Witkoff’s reaction was blunt: he “did not care” what day it was. The remark, while diplomatically unorthodox, reinforced the impression that he was more enforcer than envoy, willing to forgo niceties if they impeded his goal.
Witkoff’s rapid ascent in diplomacy has drawn inevitable comparisons to figures like Richard Grenell, another Trump ally who leapt from nontraditional backgrounds into high-stakes negotiations. Yet, unlike seasoned diplomats who see statecraft as a marathon, Witkoff views it as a series of high-stakes real estate transactions. He is, in effect, the Middle East’s newest power broker, relying less on a deep understanding of historical grievances and more on the art of leverage.
The problem is that the conflicts he is now enmeshed in are not Manhattan property disputes. In Gaza, the stakes are existential for both Israel and the Palestinians. In Ukraine, an entire European security order hangs in the balance.
While Witkoff’s track record remains unproven, his ability to bring both conflicts to a resolution will define whether he is a genuine diplomatic force or simply the latest experiment in Trump’s preference for unconventional envoys. Either way, his tenure as Trump’s dealmaker-diplomat is a reminder that, in this administration, power belongs not to the seasoned statesmen but to those who know how to work a room and, perhaps, a golf course. And whatever the outcome of negotiations over Gaza and the Ukraine-Russia conflict, Steve Witkoff will learn that in global diplomacy, some negotiations don’t come with an easy closing date.
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