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Getting to know Trump’s Middle East team
With three weeks to go until Donald Trump’s inauguration, here’s a quick look at some of the key figures who will shape his future administration’s policies toward Israel and the Middle East.
1. Steve Witkoff, the golf Partner
Who is Witkoff? A lawyer turned real estate mogul, Steve Witkoff first knew Donald Trump as a client, later becoming a personal friend and golf buddy. Witkoff was, in fact, next to Trump on the Florida golf course in September when the Secret Service discovered a would-be assassin hiding in the bushes with a loaded rifle.
During the recent election cycle, Witkoff played an instrumental role in the campaign, helping Trump’s fundraising efforts among wealthy Jewish donors from the business world. A staunch supporter of Israel, Witkoff said that after President Joe Biden’s decision to pause an arms shipment to Israel, he raised “six-figure and seven-figure donations” from Jewish donors who were dismayed by Biden’s policy. Witkoff gave upwards of $2 million of his own money to the Trump campaign and has generously supported other Republican candidates.
What will he do in Trump’s administration? Shortly after the election, Trump named Witkoff as the next special envoy to the Middle East. Witkoff has since (last month) travelled to the region and met with officials involved in negotiations over a Gaza cease-fire and hostage release deal.
The role of special envoy is somewhat elusive and is not clearly defined. Trump, who relied heavily on the work of his special envoys during his first term, likely sees a similar role for Witkoff as that previously filled by son-in-law Jared Kushner, who helped negotiate the Abraham Accords.
Witkoff fits the profile perfectly: A successful real-estate dealmaker, tasked with what the incoming president sees as the greatest real-estate deal of all—Middle East peace.
What to keep an eye on: Witkoff comes to the job with zero experience in diplomacy and foreign policy. In the Trump world, being an outsider is actually a plus, but the veteran businessman could face difficulties both in navigating the intricacies of Middle East diplomacy and in overcoming the Washington bureaucracy.
Another issue that might impact Witkoff’s effectiveness is his ties in the region. On the one hand, he is known as a fan of Benjamin Netanyahu who described the Israeli PM’s speech to Congress earlier this year as a “spiritual” experience. On the other hand, he also has a record of deep business ties with Qatar and the UAE, which could either put into question his impartiality as a mediator or, on the flip side, make him a uniquely equipped negotiator with ties on all sides of the conflict.
2. Massad Boulos, the in-law
Who is Boulos? Massad Boulos, a wealthy Lebanese-American businessman, entered the Trump sphere through marriage. His son Michael is married to Trump’s daughter Tiffany. An heir to a successful family automotive business, Boulos moved to the United States as a teenager and later joined the company. Though some have described him as a billionaire, several reports have described his wealth in more modest terms.
Boulos hit it off with his in-law Trump, and their personal friendship evolved this year into a political partnership. Boulos took it upon himself to serve as Trump’s unofficial liaison to the Arab-American community, spending time with undecided Arab voters in key states, especially Michigan, working to convince them to vote for Trump. Boulos, alongside others, succeeded in carrying out a seemingly impossible task: convincing Arab and Muslim voters to turn their back on the Democratic Party and cast their vote for a candidate who in the past sought to impose a ban on immigration from Muslim countries and who has sided time and again with Israel in its conflict with the Palestinians. Boulos rode the wave of anti-Biden sentiment among Arab-Americans because of the war in Gaza, promising them that Trump will be a president who ends the war.
What will he do in Trump’s administration? Boulus will serve in a new role announced by Trump—senior adviser on Arab and Middle Eastern affairs. Just as with Witkoff, Boulos’s exact role is yet to be defined. But he has already met with Arab leaders, including Mahmoud Abbas, head of the Palestinian Authority, a move that indicates Trump would like to see his new senior adviser do with Arab leaders the same magic he has done with Arab voters in Michigan. Boulos could be the one tasked with building trust between Middle East players and Trump and delivering the message that the region is better off with the businesslike approach of the new president, rather than the more ideological standpoint held by his predecessors.
What to keep an eye on: Boulos, though having lived most of his life in the United States, maintains strong ties with leaders in Lebanon. This could give him a leg up when working to stabilize Lebanon now that the Biden-brokered cease-fire between Israel and Hezbollah is in place.
However, like Witkoff, he comes to the position with no previous diplomatic experience, and it is unknown how effective he’ll be as a negotiator. Furthermore, as is the case with most special envoys and advisers, his work could, and likely will, clash with that of State Department diplomats and National Security Council officials, who are already engaged in the field.
Israelis know little about Boulos and are working to figure out his positions and attitudes. As of now, said one Israeli official, he seems to be coming from a very Trump-like perspective on the Middle East, one that prefers big gestures and immediate solutions to long-term, in-depth conflict resolution. For Israel, this means a top White House adviser who has an open door to Arab leaders and an open mind to the wishes of Israel’s government.
3. Mike Huckabee, annexation evangelist
Who is Huckabee? A cheerful warrior devoted to all conservative causes, Mike Huckabee is a well-known figure in American political life. A former governor of Arkansas who once ran for the Republican Party’s presidential nomination, Huckabee has used his pulpit as a leading Christian-evangelical preacher and political commentator to advance a pro-Israel, pro-settler worldview.
Huckabee not only describes himself as a Zionist, he has also played a significant role in strengthening ties between the evangelical community and Israel’s right wing, as well as in supporting Jewish settlements in the West Bank. Last week, speaking at an event hosted by a pro-settlement fundraising organization in New York, Huckabee expressed his outright support for Jewish presence in the West Bank, which he refers to as Judea and Samaria, and added that “the greatest friends that the Jewish people and Israelis have are often those of us who are evangelical Christians.” Huckabee has long voiced his support for Israeli annexation of the West Bank.
What will he do in Trump’s administration? The choice of Huckabee to serve as the next U.S. ambassador to Israel was somewhat surprising. Ambassadorships, when not held by professional foreign service officers, are either given to major donors or to those uniquely involved in the subject matter. Huckabee is neither, but his nomination demonstrates Trump’s wish to maintain his partnership with the evangelical community, while at the same time giving a nod to the settler community and its backers among Jewish Americans.
As ambassador, Huckabee is expected to carry out the Trump administration’s policies, not advance his own worldview. He even said so at a recent event, noting that he will not be the one making decisions regarding the future of Judea and Samaria.
But Huckabee can look back at the tenure of Trump’s previous ambassador to Israel, David Friedman, who used his position not only to represent the U.S. government’s views but also to advance his own positions regarding Jerusalem, the settlements and the Israeli-Palestinian conflict.
What to keep an eye on: Huckabee can expect a warm embrace from Netanyahu, from his right-wing coalition and from many in the Israeli public. His expressions of love for Israel, supported by numerous trips to the country, make Huckabee a valuable bridge to Israel’s current leadership. But what happens if Trump decides to embark on a Middle East peace deal? (Remember the “deal of the century?”) At that point, Huckabee may find himself in a tough spot, having to represent a policy that he wholeheartedly opposes.
4. Adam Boehler, Mr. Abraham Accords
Who is Boehler? Adam Boehler was a well-known face in Trump’s previous administration, although he never came across as a MAGA Republican or as a member of Trump’s inner circle.
Boehler, a businessman who now runs a healthcare investment firm, served as CEO of the U.S. International Development Finance Corporation, a federal agency created by Trump. But Boehler’s claim to fame comes from his involvement in brokering the Abraham Accords, which normalized relations between Israel and four Arab states. Working with Jared Kushner and his team, Boehler played an important role in turning the deals with the UAE and Bahrain into reality and in helping all sides forge business and trade relations, which have kept the Accords afloat even during the turbulent times that have engulfed the region.
What will he do in Trump’s administration? Boehler will serve as Trump’s special envoy for hostage affairs. This role has taken on added importance in the past year, since the special envoy’s primary task right now involves achieving the release of American hostages held by Hamas in Gaza, alongside of dealing with other cases of U.S. citizens unlawfully held in other countries. It is still unclear who will serve on Trump’s team negotiating the Gaza cease-fire and hostage release deals, a team that in the Biden administration was led by heads of the CIA, State Department and the National Security Council, with Biden’s top Middle East adviser in charge of the daily work aimed at reaching a deal. Boehler may or may not be part of the team, but he has already indicated his intention to be involved and to help implement Trump’s threat of “all hell to pay” if the hostages are not released.What to keep an eye on: It’s a crowded field, and Boehler might find himself stepping on other administration officials’ toes when trying to reach a hostage release deal. He will also face the need to shape a new U.S. doctrine toward the issue of unlawfully held Americans overseas: One key question is whether the Gaza experience should change U.S. policy of not negotiating with terrorists. At least one hostage family has urged Boehler to do so.
5. Elise Stefanik, the college president slayer
Who is Stefanik? New York Congresswoman Elise Stefanik’s breakout moment on the national scene came in December of 2023, during a congressional hearing with presidents of three elite universities concerning the outbreak of antisemitism on college campuses. Stefanik, combining rhetorical skills and what seemed to be a deep-felt disdain for college presidents, grilled them regarding their institutions’ respective response to expressions of antisemitism in the months following Hamas’s October 7 attack on Israel. She successfully cornered the universities’ top executives, ridiculing their politically correct responses and taking credit for the resignation of all three of them.
An outspoken Trump supporter even before the hearing, Stefanik has gained admiration in Republican circles, as well as among many Israeli politicians and opinion leaders.
What will she do in Trump’s administration? On November 11, Trump tapped Stefanik to serve as the next U.S. ambassador to the United Nations, a cabinet-level position. It is one of the top posts in America’s foreign service; while exercising diplomatic skills, the ambassador also serves as the face of American policy on the global scene’s most important stage.
As ambassador, Stefanik’s oratorical skills and her quick responses are likely to prove a valuable asset, especially when it comes to issues relating to Israel. The UN has long been known for its critical—and at times hostile—approach toward Israel. More often than not, the U.S. ambassador is the sole voice supporting Israel in the international body.
What to keep an eye on: The UN is about more than speeches. The upcoming year will force Stefanik to deal with some difficult diplomatic maneuvers at the UN, which will test the Trump administration’s support for Netanyahu’s Israel. Among the issues likely to come up are the growing demands of Arab nations, supported by many others, to penalize Israel or to use the powers of the UN to stop its military actions in Gaza and ensure humanitarian support for Gazan civilians. The UN may also be facing a critical moment regarding Iran, as the Islamic Republic speeds up its nuclear program and continues to support anti-American and anti-Israeli proxies in the region. Alongside fiery speeches, Stefanik will also need to create coalitions and negotiate compromises with America’s allies to ensure the UN advances U.S. policy goals, rather than undermining them.
Top image credit: Gage Skidmore.