While it’s too early to predict how history will ultimately view Steve Witkoff—President Trump’s Special Envoy to Everywhere Challenging—this week marks a significant moment in his career.

Consulting with seasoned foreign policy experts revealed that few could recall a recent period as eventful as the whirlwind tour Witkoff just concluded.

In merely four days, the 68-year-old Witkoff engaged in pivotal meetings with Israeli Prime Minister Benjamin Netanyahu regarding the complex Gaza peace process, traveled to Abu Dhabi to discuss the ongoing Ukraine-Russia conflict, and wrapped up his week in Oman to negotiate with Iranian officials on their nuclear ambitions and additional concerns.

These efforts spanned three of the globe’s most contentious diplomatic hotspots. Just four days. One individual.

Once a real estate lawyer who transitioned into development, Witkoff was virtually unknown in diplomatic circles until a couple of years ago. Now, the billionaire and golf companion of President Donald Trump has become a prominent figure in U.S. diplomacy.

Yet, Witkoff’s journey to prominence has been neither straightforward nor devoid of setbacks. Merely two months back, there were calls for his dismissal following the leak of a recorded conversation with a top Russian foreign policy advisor, where Witkoff appeared to offer the Kremlin advice on exerting pressure on Ukraine and handling President Trump.

Democrat Ted Lieu called him a ‘traitor’. Some Israeli officials have harshly criticized him. And right-wing hawks are doggedly undecided on the Long Island-born emissary.

But I can now report, after speaking to half a dozen White House officials, including Secretary of State Marco Rubio, that Witkoff’s unconventional style, far from costing his role, is perceived to be the secret to his success.

Three of the world’s most volatile diplomatic arenas. Four days. One man (Pictured: Witkoff with Jared Kushner (L) and Omani Foreign Minister on February 6)

A real estate lawyer-turned-developer, Witkoff was unknown in diplomatic circles just a couple of years ago

Two months ago, there were bipartisan calls for his ousting over a leaked recording of a call to Vladimir Putin’s top foreign policy aide (Pictured: Putin and Witkoff in August 2025)

Perhaps, it’s no wonder that much of the media has been strangely muted about Witkoff’s historic portfolio as it plays out in real time, indicating dual yet conflicting conceptions of him.

One: he is inconsequential. And two: his diplomatic appearances are so frequent that they now seem routine. Both cannot be true. Yet somehow, in the strange ecology of Washington’s permanent commentary class, they coexist.

The gap between what President Trump has entrusted Witkoff to do and what he has already accomplished — and the disdain with which he has been treated by members of the press and the foreign policy establishment — has never been wider.

The most prominent coverage of Witkoff since he stepped into this multifaceted role has consisted of several hit pieces in major newspapers, complete with anonymous quotes questioning his lack of formal credentials, mocking his negotiating style, and even taking shots at his intelligence.

Indeed, it is the oldest story in Washington: the outsider who did not come up through the conventional and approved channels is suspect.

Witkoff already has effectuated one major feat: just a little thing called Middle East peace, as Donald Trump might say.

After months of grinding warfare in Gaza and intense regional pressure, Witkoff played a central role in helping broker the ceasefire-and-hostage framework that halted major combat, enabled humanitarian corridors, and set out phased steps toward longer-term stabilization between Israel and Palestine.

All the while he has partnered on the project with Jared Kushner, the president’s son-in-law and Witkoff’s frequent collaborator in maverick foreign diplomacy, who has also been his cohort this week.

Working in concert with Israeli leaders, regional intermediaries and American officials, Witkoff helped move the parties from rhetorical trench warfare to a workable, if still fragile, agreement which was finalized after weeks of shuttle diplomacy and round-the-clock talks.

After months of grinding warfare in Gaza, Witkoff played a central role in helping broker the ceasefire-and-hostage framework (Pictured: Witkoff in Israel May 2025)

All the while he has partnered on the project with Jared Kushner, the president’s son-in-law

The deal represents the most significant diplomatic breakthrough in the conflict in years, but it does not solve every problem. No serious person claimed it would.

However, the 2025 Israel-Gaza ceasefire agreement (otherwise known as Trump’s 20-point Gaza peace plan) largely stopped most of the killing, opened the door to reconstruction, and created space for further negotiations.

In today’s Middle East – and certainly in the history of the world – that counts as real progress and a genuine relief to the citizens on the ground.

That achievement only cemented what has been, from the start, the president’s deep confidence in Witkoff’s ability to get things done.

Trump’s trust also was validated by Witkoff’s role in helping secure the release of Americans held abroad.

Working quietly with intermediaries, allied governments and adversarial regimes, Witkoff has been involved in efforts that led to the return of multiple US citizens detained in places where diplomacy is often frozen, such as Russia and Gaza.

In several cases, he was dispatched personally to conduct sensitive conversations, leveraging his access to Trump and his reputation as a straight-talking dealmaker. Families who had waited months – sometimes years – to hear their loved ones’ voices know his name, even if cable news viewers do not.

One might think that Secretary of State and national security adviser Marco Rubio might chafe at the high-profile, high-stakes responsibilities Witkoff has been given, but Rubio is among the many fans Witkoff has inside the White House.

Rubio told me in a statement for this column, ‘Steve is a key member of President Trump’s team and plays an indispensable role in advancing the President’s priorities. His unique perspective and innovative approach open new opportunities for diplomacy that were previously unavailable. It’s been remarkable to see him in action and a privilege to call him a colleague.’

One might think that Secretary of State Marco Rubio might chafe at the high-profile, high-stakes responsibilities Witkoff has been given, but Rubio is among the many fans

Lest you think that statement is pro forma fakery masking jealousy or resentment, I can report that it is not. Rubio, Vice President JD Vance, Homeland Security Advisor Stephen Miller, and White House Chief of Staff Susie Wiles are all among those in the President’s uppermost inner circle whose private assessments of Witkoff match their public praise.

In a building famous for whisper campaigns, that consistency matters.

Trump’s history with Witkoff helps explain the trust.

The two men have known each other for decades, dating back to their days in New York real estate and business circles. They bonded over deals, loyalty, and a shared skepticism of elite opinion. Witkoff was there in Trump’s pre-political life, during setbacks and successes, long before polls and primaries entered the picture. To Trump, that counts for more than résumés and seminar credentials.

As for his supposed inexperience, history offers some perspective. Henry Kissinger had no practical diplomatic background when he began engaging with the Soviet Union. Kushner had little foreign policy experience when he helped push through the 2020 Abraham Accords, which normalized relations between Israel, the United Arab Emirates, Bahrain, and later Morocco.

Results, not pedigree, are what should matter and what endure.

To be sure, the final chapters of the Iran negotiations and the Ukraine-Russia conflict have yet to be written. Diplomacy is a long game, and victories can be ephemeral or evaporate. But even short-term agreements save lives and form important foundations for the future.

In addition to Secretary Rubio, I spoke to a number of White House officials about Witkoff.

White House spokeswoman Olivia Wales told me, ‘Thanks to President Trump’s leadership and the Special Envoy’s efforts, all Israeli hostages have been returned, there is peace in the Middle East, and Americans detained abroad have come home. These remarkable accomplishments have cemented Special Envoy Witkoff’s legacy as a consequential peacemaker, and he is continuing to work every day on behalf of the American people.’

Another White House official I spoke to channeled the deep frustration in the West Wing with both the media and foreign policy institutions. ‘There have been a number of hit pieces [but] the results speak for themselves,’ my source said pointedly. ‘A lot of people wanted this to fail, including institutionalists in the media.’

The official added, ‘Untraditional backgrounds actually get better results. Joe Biden’s team was experienced and had numerous foreign policy failures… There is a misconception that more expertise leads to better foreign policy outcomes.’

When Witkoff sits across from foreign leaders, they know he speaks with the president’s full authority. There is no daylight. No guessing game about who really matters. 

Witkoff’s guiding instinct is simple: close the deal. He approaches diplomacy the way he approached real estate — understand leverage, read the room, move both fast and with purpose, and do not get lost in abstractions.

To striped-pants diplomats, this sounds crude. To President Trump, it sounds effective.

Ambassador Mark Wallace, CEO of United Against Nuclear Iran and a veteran observer of high-level negotiators, told me this about Witkoff, ‘These foreign policy challenges have been around for a very long time. Foreign policy circles can be insular and territorial. I like him.’

Wallace added one caveat: ‘Of course, there has been some broken china and the cost to repairing that china remains to be seen.’

Witkoff’s guiding instinct is simple: close the deal. He approaches diplomacy the way he approached real estate — understand leverage, read the room, move both fast and with purpose, and do not get lost in abstractions

That is the right note to end on. I know there are current and former government officials who will read this column and suggest it gives the president’s friend far too much credit. That it leaves out some of the criticism that has been directed at Witkoff, including conflict of interest questions about his family’s business interests and the manner in which he has interacted with Vladimir Putin during their many sessions together.

Those are all worthy areas of scrutiny and inquiry. But they don’t speak to the ultimate reason Witkoff, at great personal expense in terms of time and money, is doing what he is doing for his friend Donald and for the pursuit of peace in some of the most nettlesome and worrisome conflicts on the planet.

We will have to see what Steve Witkoff ultimately achieves. History is unsentimental. It tallies results, not profiles. It remembers treaties, not Twitter storms.

But for now, Trump is getting exactly what he wants: someone like him. Someone whose lack of traditional credentials has invited mockery and derision. Someone who is underestimated. Someone who works relentlessly. Someone who believes that stubborn problems exist to be solved, not endlessly managed. Someone who believes in results.

In an age of paralysis, that is not nothing.

It may, in the end, be everything.