From Property Deals to Peace Deals: Who Is Steve Witkoff, Trump’s Gaza Envoy?

Donald Trump often casts himself as a “man of peace,” a unifier whose proudest legacy would be ending global conflicts. But when it came to one of the world’s most volatile regions, he didn’t turn to decorated generals, seasoned diplomats, or career negotiators.

He turned to Steve Witkoff, a billionaire New York property developer.

So, who is this real estate tycoon, and why was he tasked with brokering peace in the Middle East? Our deep dive explores how a landlord with no diplomatic background became Trump’s unlikely envoy. From a deep personal tragedy and a long-standing friendship with Trump to his openly pro-Israel stance, we uncover what it means when a complex geopolitical crisis is treated like a property development project.

The Unlikely Friendship: How a Landlord Became a Presidential Confidant

To understand Steve Witkoff’s role, you have to understand his relationship with Donald Trump, a bond that stretches back decades and was solidified by personal tragedy.

A Real Estate Idol and a Gritty Rise

In the 1980s, Steve Witkoff was a young lawyer in Manhattan who looked up to a “larger than life” Donald Trump. “He was like the Michael Jordan to me… of the real estate business,” Witkoff recalled. Inspired by Trump’s “swashbuckling style,” he quit law in 1985 to carve out his own empire by purchasing run-down apartment buildings.

His approach was unconventional. He wasn’t a distant landlord; he collected rent himself, sometimes with a pistol strapped to his ankle, and even handled plumbing repairs. It was a gritty, hands-on path that eventually led to billionaire status and a friendship with his idol, sparked by a chance encounter where Witkoff paid for Trump’s sandwich. From that day on, they were inseparable, building their connection over golf games and shared meals while pursuing a joint ambition to create a billion-dollar real estate empire.

A Bond Forged in Tragedy

In 2011, Witkoff’s world was shattered when his son, Andrew, died from an opioid overdose. In his devastation, it was Donald Trump who stepped in to offer comfort. The tragedy profoundly reshaped Witkoff’s perspective. He began carrying his son’s ID card and wearing his ring, inspired by Andrew’s quiet compassion for the homeless people near his apartment.

This personal loss became a calling. Believing he could honour his son’s spirit by working towards peace, Witkoff asked Trump for a promise: if re-elected, let him try his hand at Middle East peace. With no formal plan or diplomatic experience, Trump agreed on the spot.

The Real Estate Approach to Geopolitical Conflict

Witkoff’s strategy for peace is rooted entirely in his real estate philosophy: “A good deal has to work for everybody.” He believes the key is to put himself in the other person’s shoes to understand what they truly want. While effective for closing a property deal, applying this model to the Israeli-Palestinian conflict reveals critical flaws.

A Negotiation with One Side Missing

To have a successful negotiation, you need to understand all sides. Yet, when asked if he had ever spoken directly with Hamas, a key player in the conflict, Witkoff admitted that he had not.

Key Issues with this Approach

• Reliance on Intermediaries: Witkoff stated he trusts the Qataris to represent Hamas’s position. This secondhand approach prevents direct assessment and understanding.
• Pre-judged Outcomes: Without a direct conversation, Witkoff declared Hamas’s goals unacceptable, raising questions about the fairness and integrity of the process.

As he put it, negotiating without the other party present is “a little bit weird.” This gap in communication is more than an inconvenience; it’s a fundamental failure in a diplomatic process that demands nuance and direct engagement.

“Making judgments without ever hearing one of the central actors raises critical questions about the integrity of the process itself.”

Redeveloping Gaza: A Property Plan, Not a Peace Plan

Although Witkoff took the rare step of touring Gaza to see the situation firsthand, the solutions he proposed sounded more like a developer’s pitch than a diplomatic resolution.

His ideas centred on:

• Golf investments
• Land swaps
• Demilitarisation in exchange for investment

This outlook aligns perfectly with Donald Trump’s controversial vision for Gaza, which involved permanently displacing Palestinians to create a “luxury holiday destination.” Witkoff defended this as a “realistic” assessment of Gaza’s needs, but critics saw it as a plan that completely ignored the human and political realities on the ground.

These proposals fail to address the root causes of the conflict:

• Israel’s ongoing military actions and blockade.
• The occupation of the West Bank.
• The right of return for Palestinian refugees.

Treating these deep-seated historical and political issues as mere obstacles in a real estate trade-off is a recipe for continued conflict, not lasting peace.

A Question of Neutrality: The Broker’s “Zionist Heart”

A peace broker’s greatest asset is impartiality. However, Witkoff’s allegiances are clear. He has been described as having a “warm Zionist Jewish heart,” and David Friedman, Trump’s notoriously pro-settlement ambassador to Israel, has praised him as a “lover of Israel.”

This declared sympathy makes fair negotiation incredibly challenging. The core of his strategy is putting himself in another’s shoes, which is compromised when his own shoes are already firmly planted on one side. If a negotiator cannot approach the table with genuine neutrality, whose peace are they truly trying to make?

A Pattern of Transactional Diplomacy

Why would Trump choose a real estate developer over countless qualified diplomats? It reflects a broader pattern in his approach to governance: favouring billionaire friends and transactional deal-making over institutional expertise. Men like Peter Thiel and Larry Ellison have often been brought into the fold, prioritising business-style solutions for complex global problems.

For Trump, a successful deal brokered by Witkoff isn’t just about peace; it’s also about prestige, specifically the Nobel Peace Prize he feels he deserves.

Ultimately, Steve Witkoff’s mission in Gaza highlights the profound danger of applying a real estate mindset to a decades-old conflict defined by identity, history, and justice. While grand deals and exchanges might seem like progress, they are like building a skyscraper on sand. A just and lasting peace can only be achieved when the true foundations of the conflict are addressed. This means confronting the core issues: the occupation, the blockade, and the denial of fundamental rights.

For Gaza and Palestine, the question remains: can genuine peace ever be achieved when it’s treated as just another transaction?