Among the many appointments President-elect Donald Trump has rolled out in recent weeks, his decision to name Steve Witkoff, a longtime friend and golfing partner, as special envoy to the Middle East — a crucial role in Trump’s first term — came as an unusual casting choice.
Witkoff, a billionaire real estate executive from New York City, has no diplomatic experience and is not viewed as an authority on geopolitical dynamics in the Middle East — where tensions have risen since Trump was last in office, amid a widening regional war between Israel and several Iran-backed proxy groups. Witkoff’s past financial dealings with Qatar, which has targeted him in its lobbying, have also raised questions about conflicts of interest.
But with a direct line to the president-elect, Witkoff, a 67-year-old Jewish Republican, is expected to be a key player in conducting outreach across the region, as Trump has indicated he will prioritize expanding the Abraham Accords, with an eye on Saudi Arabia. The president-elect has also called on Israel to wrap up its wars in Gaza and Lebanon, among other goals he emphasized while campaigning.
In his statement announcing the pick last week, Trump said that Witkoff, whom he has known for decades, “will be an unrelenting Voice for PEACE, and make us all proud.”
Despite his unorthodox background, Witkoff’s acquaintances in the real estate industry as well as Jewish Republicans involved in Middle East issues also expressed confidence in his ability to succeed in the high-profile posting.
“Steve is a brilliant businessman and deal maker, with a deep understanding of Israel, its strategic importance to the United States and its potential to bring greater stability and prosperity to the Middle East,” David Friedman, who served as Trump’s ambassador to Israel in his first term and had reportedly expressed interest in the Middle East envoy role, said in an email to Jewish Insider on Tuesday.
Jon Mechanic, a real estate attorney in New York City, described Witkoff — who once kept a copy of the book Tough Jews on his desk and was known to carry a handgun during his early years overseeing distressed properties in Upper Manhattan — as a “great negotiator” who is “very good at finding a way to make a deal.”
Mechanic, who has worked with Witkoff on several deals over multiple years, said the developer would benefit from relationships he has built in the region through his real estate firm, Witkoff Group, which owns properties across the country and in London. “He’s raised money over there on both sides,” said Mechanic, referring to Israel and some of the Gulf states. “He’ll be familiar,” Mechanic added. “He’s been involved.”
Last May, for instance, Witkoff spoke on a panel about the future of cities at the Qatar Economic Forum in Doha, where he shared the stage with Khalid Ahmed Al-Obaidli, the president of Qatar’s Real Estate Regulatory Authority, among others. In his comments, Witkoff said he was optimistic about investment opportunities in Qatar because of what he called “solid government,” adding that he sensed “a strong compact between government and private business” in the Gulf kingdom.
“One can’t help but wonder if there aren’t some geopolitics at play here,” said Ben Baird, the director of advocacy for the Middle East Forum. “It’s not a sure bet how people like Witkoff are going to enact policies,” he acknowledged. “They’re not always going to benefit Qatar, and especially when you have competing interests involved, I still think they’ll do what’s best for American interests.”
In the summer of 2023, meanwhile, Witkoff had sold Manhattan’s troubled Park Lane Hotel, which had also counted Abu Dhabi’s investment firm as a stakeholder, to the Qatar Investment Authority, the country’s sovereign wealth fund, for $623 million — adding to a push into New York real estate.
But in addition to being a potential asset for Witkoff, who reportedly views Middle East geopolitics as “one giant real estate deal,” his past dealings with Qatar in particular could place the incoming envoy in an uncomfortable position, experts say — as the Gulf state has faced bipartisan criticism in Congress for hosting Hamas leadership.
The Park Lane sale came after Qatar had engaged in an aggressive and widespread lobbying effort during Trump’s first term, as the president-elect sided with Saudi Arabia and other neighboring states that had imposed a blockade on the Gulf country.
Seeking to build goodwill with the U.S., Qatar launched a campaign to influence hundreds of people close to Trump, including Witkoff, who was among several American executives to meet with Qatari officials, according to foreign lobbying disclosures that broadly describe a series of “introductions” to “facilitate collaboration” and discuss “business opportunities,” among other things.
Nick Muzin, a Republican operative who helped lead the Qatari lobbying operation, said in an email to JI that he had “introduced” Witkoff “to the Qatari leadership in 2017-2018,” but he did not respond to follow-up questions regarding the substance of their discussions or who was present for the meetings.
“Steve understands the complexities of the Middle East, is politically savvy, a good listener, and gets things done,” Muzin added. “America will benefit from his wise counsel and deal-making skills in the years ahead.”
But Ben Baird, the director of advocacy for the Middle East Forum, a conservative policy think tank, expressed concerns that Witkoff had been targeted by Qatar — suggesting the hotel sale was part of what he called an ongoing “charm offensive” reaching within “Trump’s inner circle of billionaire policymakers,” including Elon Musk and others.
“One can’t help but wonder if there aren’t some geopolitics at play here,” said Baird, whose group launched a campaign after the Oct. 7 attacks urging U.S. private equity and hedge fund leaders to stop doing business with Qatar. “It’s not a sure bet how people like Witkoff are going to enact policies,” he acknowledged. “They’re not always going to benefit Qatar, and especially when you have competing interests involved, I still think they’ll do what’s best for American interests.”
“Steve has proven himself, over decades, to be someone who is smart, creative, resourceful and someone who knows how to get things done,” Bob Knakal, a veteran real estate broker in New York City who has known Witkoff for several years, told JI. “Based on seeing him operate so adroitly in the trenches of New York City real estate all these years, I am confident he will succeed and do a great job in his new role.”
“Nevertheless,” he told JI, “ it is troubling that so many from Trump’s inner circle have accepted such deep investments from the Qataris.”
Witkoff did not respond to emails seeking comment, and the Trump transition team did not respond to a request for comment regarding the president-elect’s vision for the role. The Qatari Embassy also did not return a request for comment about its outreach to Witkoff.
“Steve has proven himself, over decades, to be someone who is smart, creative, resourceful and someone who knows how to get things done,” Bob Knakal, a veteran real estate broker in New York City who has known Witkoff for several years, told JI. “Based on seeing him operate so adroitly in the trenches of New York City real estate all these years, I am confident he will succeed and do a great job in his new role.”
Previously, Witkoff, who lives in South Florida and until recently had little to no known involvement in politics, had served as an informal advisor to Trump on tax cuts, opioids and pandemic-related business issues. During the election, he took an active role in the campaign, helping to link Trump with Jewish donors who had become angered over President Joe Biden’s approach to Israel following Hamas’ Oct. 7 terror attacks.
A staunch defender of Israel, Witkoff, who was in the audience for Israeli Prime Minister Benjamin Netanyahu’s address to a joint session of Congress last July, has also raised money for some pro-Israel causes.
But his involvement in such philanthropic efforts has not been particularly significant, according to a prominent Jewish leader in New York City who has briefly crossed paths with Witkoff and was granted anonymity to speak candidly about the incoming Middle East envoy. “I don’t remember seeing his name on Jewish fundraisers,” the Jewish leader noted.
As he prepares to assume his new position in government, Witkoff, who is also serving as a co-chair of of Trump’s inaugural committee, has already reportedly been reaching out to countries in the region, while seeking input from Jared Kushner, Trump’s son-in-law, who played a major role in brokering the Abraham Accords, normalizing relations between Israel and several Arab nations.
Weeks before he officially takes over as Middle East envoy, meanwhile, Witkoff — who helped to launch Trump’s new crypto venture — is slated to speak at a Bitcoin conference in Abu Dhabi, alongside Paul Manafort and Eric Trump, among other industry advocates.
Prematurely, the listing for the event, which runs from Dec. 9-10, describes Witkoff as “Special Envoy to the Middle East, Trump Administration,” noting that he “is now focused on the intersection of real estate, Bitcoin, and crypto,” as a biographical blurb states.
In a statement to JI on Wednesday, a spokesperson for the event, Kristyna Mazankova, said Witkoff “is coming to the conference, in his personal capacity, to talk about bitcoin.”
“We list him as Middle East envoy in the Trump administration because he was recently named to the post,” she clarified, “and it is therefore hyper relevant to the conversation, even though he will not be officially representing the administration, which will not have begun as of the time of the conference.”