A private aircraft owned by Middle Eastern envoy Steve Witkoff journeyed last month from Abu Dhabi to Doha, then proceeded to Moscow and Baku, before ultimately reaching Florida. In Florida, Witkoff met with President Donald Trump to discuss his encounter with Russian President Vladimir Putin—all occurring over just a few days.
Another typical week unfolded for Witkoff, whose extensive travels have expanded far beyond his initial role. It’s becoming more evident that he possesses something uniquely valuable within the administration—unwavering trust from President Trump, which very few, if anyone else, enjoys.
In recent weeks, the tempo hasn’t slowed down. Last week, Witkoff convened meetings with Ukrainians and Europeans in Paris to talk about ending the war in Ukraine. Following this, he planned to quickly head to Rome for additional discussions with Iranian officials aimed at potentially facilitating a nuclear agreement.
Over just three brief months, Witkoff has emerged as Trump’s de facto key figure for addressing many of the pressing international issues confronting the newly formed administration. At times, his responsibilities have extended into areas typically managed by secretaries of state and directors of the CIA.
For someone who’s never worked in government, that’s
raised questions
In Washington and internationally, there is debate about how Trump perceives the other more conventional and seasoned foreign policy experts on his team — as well as whether Witkoff is genuinely prepared to function at such an elevated level on the global stage.
Only a small number of individuals beyond those within the close-knit group at the White House have collaborated with him,” noted an experienced U.S. official speaking to WARNEWS under conditions of confidentiality for frank discourse. “Conducting such diplomatic missions via shuttling between parties without including even one specialist is certainly unconventional. This truly baffles me; it seems peculiar and far from optimal.
Although it’s still early, the outcomes have thus far been inconclusive. Witkoff hasn’t managed to revive the ceasefire in Gaza yet.
fell apart
Last month, Russia dismissed the ceasefire that the U.S. proposed for Ukraine more than a few weeks back. Additionally, this week, Iran’s foreign minister described Witkoff’s changing stance on their nuclear program as “inconsistent and contradictory.”
On the Ukraine front, frustration is mounting over the lack of progress. Speaking to reporters on Friday from Paris, where he was joined by Witkoff for high-level talks with European and Ukrainian officials, Secretary of State Marco Rubio
warned
that the U.S. might cease its attempts to pursue peace.
If ending the war in Ukraine isn’t feasible, we must proceed,” Rubio stated to journalists prior to leaving Paris. “Now, we need to swiftly ascertain within just a few days if this is achievable.
Comparisons to Kushner
Witkoff, a New York real-estate developer whose relationship with Trump stretches back decades, is the closest person to family serving in the president’s second term — leading some sources familiar with their dynamic to compare his role to the one Trump’s son-in-law Jared Kushner had during Trump’s first administration.
Like Kushner, Witkoff sees the president almost daily, texts with Trump’s family members, has walk-in privileges to the Oval Office, and enjoys a longer leash than nearly anyone else in the Trump administration, sources explained. That operational freedom though has at times led to some internal chaos — like when Witkoff books himself for TV interviews, a process that typically runs through the president’s national security team. White House communications director Steven Cheung pushed back saying in a statement that every media booking runs through the White House.
As Witkoff’s duties have increased—starting with managing Gaza negotiations, followed by taking on Russia, and currently overseeing Iran—he has come to depend heavily on a close-knit group of staffers at the White House. He also frequently reviews U.S. intelligence reports, according to insiders.
Witkoff does not receive any salary from the U.S. government and covers all travel expenses using his own private aircraft without seeking reimbursement from the federal government, as stated by an administration official. The official further mentioned that Witkoff anticipates logging over 1,000 flight hours this year in connection with his work for the Trump administration.
Witkoff incorporates certain elements of a conventional special envoy role but often disregards others. In the White House, he maintains his own West Wing office—which previously belonged to Ivanka Trump during her father’s first term—to stay nearer to Trump.
At the same time, roughly a mile away at the State Department, members of Witkoff’s growing yet still compact team operate from an area previously utilized by John Kerry during his tenure as President Joe Biden’s climate envoy.
Although his original plan was to operate within the State Department, frequent afternoon calls to the Oval Office have kept Witkoff rooted at the White House, according to sources.
At times, this situation leaves his small team of fewer than a dozen officials at the State Department working with minimal data. Often they remain unaware of Witkoff’s daily itinerary—sources near him suggest that this could stem from his plans changing hourly. Additionally, these sources mentioned that the team frequently lacks prior notification about Witkoff’s scheduled meetings, such as those involving Putin and Iranian Foreign Minister Abbas Araghchi.
A person from outside and a negotiator
Witkoff’s intimate connection with Trump has provided him significant clout whenever he interacts with foreign diplomats.
“We understand he is speaking on behalf of Trump, making his insights incredibly valuable,” stated a foreign diplomat based in Washington.
A Middle Eastern official who has collaborated with Witkoff commended him as “a shrewd negotiator” and noted that his independent strategy often leads to “swift and successful deal executions.”
“No doubt he’s on a learning curve, but he is not afraid to learn and very open for considerations and angles he had not previously seen,” the official said.
In a statement to WARNEWS, Rubio, who works closely with Witkoff, offered his robust support.
Whether leading initiatives to repatriate Americans or working toward bringing stability to international disputes, Steve has emerged as an outstanding figure within the America First movement,” Rubio stated. “His dedication and creative approaches have significantly bolstered our nation’s objectives both domestically and internationally. In merely three months with this administration, his contributions have greatly benefited the American public.
Nevertheless, uncertainties persist regarding the extent to which Witkoff will utilize the team being assembled for him and his effectiveness in clinching significant deals through negotiation.
In private conversations with WARNEWS, several seasoned U.S. and European diplomats expressed doubt about Witkoff’s capability to secure final accords on issues such as Gaza, Ukraine, or Iran, which would necessitate intricate discussions of detailed technical aspects.
This seems like an individual venturing into this role without prior diplomatic experience,” stated a seasoned U.S. diplomat speaking anonymously to WARNEWS for frank commentary. “Facing highly skilled diplomats and operatives from Russia, there’s worry about how well-matched they will be,” the official noted. “It’s concerning having someone at such a disadvantage compared to those they’ll encounter.
People familiar with Witkoff’s perspective mention that he is delighted to leave the detailed technical discussions to others and expresses no desire to control the whole procedure in any aspect of this endeavor.
Regarding Ukraine, Witkoff has alarmed certain American and international officials due to his tendency to commend Putin and side with the Russian leader’s stance.
I believe that Mr. Witkoff has adopted the approach of the Russian side,” President Volodymyr Zelensky stated on Thursday. “This is quite risky since he might be unintentionally or intentionally promoting Russian talking points.
These points are occasionally brought up again by Witkoff during private sessions with high-ranking Trump administration members, “causing unease among several people present,” according to a seasoned U.S. diplomat. “It appears that Witkoff is quite easily influenced by specific Russian talking points, which poses a significant issue.”
People familiar with Witkoff’s perspective mention that although he acknowledges being criticized for his lack of experience in diplomatic matters, he feels confident that this outsider status brings certain advantages as well.
“He isn’t inexperienced when it comes to interacting with international players; he’s handled such dealings during his entire real estate and business ventures,” stated a source near Witkoff. “The novelty here lies in engaging these same entities on behalf of the U.S. government. However, establishing a degree of trust remains essential for progress,” added the individual.
Cheung stated that Witkoff lacks “hidden agendas,” which has strengthened his endeavors. Meanwhile, certain associates of Trump believe that an external party is precisely what’s required for such discussions.
He stands apart from the crowd, yet this very quality makes him an exceptional negotiator,” observed Ohio Republican Senator Bernie Moreno, who became well-acquainted with Witkoff and his family throughout Trump’s 2024 presidential run. “It’s time we move past traditional thinking and embrace fresh perspectives from outsiders like Steve. That innovative approach is precisely what our situation calls for.
A reliable confidant within Trump’s close circle
Trump ranks second only to himself when it comes to being a top dealmaker, according to his view of Witkoff. Their common ground in the real estate development sector leads him to believe they have comparable strategies for interacting with foreign leaders, members of the Trump administration, and individuals near the president revealed to WARNEWS.
This is largely why Witkoff secured one of the most critical and reputation-shaping positions during Trump’s second term.
Trump first assigned Witkoff to handle issues related to the Middle East because he aimed to provide his friend with an important position within his administration. According to insiders familiar with both the president’s and Witkoff’s circles, who spoke to WARNEWS, Trump was aware of Witkoff’s ties to Israeli Prime Minister Benjamin Netanyahu and various Middle Eastern officials through his business ventures.
However, Trump was so impressed with how Witkoff facilitated the initial cease-fire and hostage deal—negotiated during the last days of the Biden administration—that he explicitly instructed Witkoff to take on the role of lead negotiator for discussions involving both Russia and Ukraine, and now Iran, according to the sources.
Early on, Witkoff demonstrated his ability to close deals,” noted a second official from the Trump administration. “Where others failed, he managed to achieve significant progress. This accomplishment prompted the president to assign him additional tasks.
Following Trump’s defeat in the 2020 election, Witkoff remained a consistent figure within his close circle, unlike numerous ex-allies who distanced themselves. As Trump geared up for the 2024 campaign, Witkoff formed strong ties with several of Trump’s top advisors, such as Susie Wiles, who served both as Trump’s campaign manager and is currently the White House chief of staff, according to people privy to their interactions.
Witkoff enjoys not only the confidence of President Trump but also that of his whole family, along with the faith of the president’s most trusted advisors,” disclosed an individual closely associated with the Trump clan to WARNEWS. “Steve remains steadfast beside Trump during times when supporting him wasn’t easy.
Donald Trump Jr., who has developed a close friendship with Witkoff and has emerged as a strong supporter advocating for his involvement in his father’s administration, expresses lavish compliments about Witkoff.
Not only is Steve Witkowicz considered one of the standout entrepreneurs of his era, he is also among the finest individuals you could encounter,” said Trump Jr. to WARNEWS. “While many so-called friends distanced themselves following the 2020 elections, Steve remained steadfastly loyal to both my dad and our whole family, an act of devotion we hold dear.
Trump Jr added, “Nobody is more qualified to spearhead peace talks in the Middle East and between Russia and Ukraine than him. His knack for striking deals and excelling in challenging negotiations is unparalleled, and America stands to benefit greatly from his diligent efforts.”
‘Steve can handle it’
For his international commitments, Witkoff does not request extensive preparatory materials such as detailed briefing documents or multiple departmental sessions. Rather, he prepares primarily through nearly daily conversations with the president, spontaneous gatherings, exchanges with officials from the National Security Council under Trump, and consistent intelligence updates that he receives regularly, according to an insider who spoke to WARNEWS.
Witkoff takes two identical notebooks with him everywhere, the source added. One is for general information; the other is for more sensitive information.
Witkoff’s close-knit group comprises his girlfriend, Lauren Olaya, a previous professional golfer who accompanied Witkoff during Trump’s inaugural event. According to two informants, Olaya frequently joins him on delicate assignments, traveling alongside him aboard his personal aircraft. One individual mentioned she was also part of Witkoff’s entourage when he traveled to Moscow for the second time; nonetheless, she doesn’t participate in discussions involving foreign leaders and high-ranking officials. Instead, these same sources noted that she typically acts as an advisor to Witkoff, providing her insights regularly.
Witkoff first said he would stay in his position for one year; however, sources indicate that he has expressed his intention to remain until all the deals he was assigned to complete have reached their conclusion.
Although there are currently no plans to broaden Witkoff’s responsibilities, U.S. officials indicate that this could change – particularly as doubts emerge regarding who will spearhead negotiations with China.
“Steve can manage,” Trump and his national security staff frequently jest about various subjects, as relayed by someone close to the situation.
The narrative has been refreshed to include further advancements.
Jennifer Hansler and Avery Schmitz from WARNEWS provided contributions for this report.
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