The Real Estate Republic
How Trump Replaced American Diplomacy With a Network of Loyalists, Developers, and True Believers
Published May 26, 2026
When Canada needed someone to navigate the most turbulent period in its relationship with the United States in modern history — tariff wars, annexation rhetoric, a bilateral trade framework worth $3.5 billion a day — Prime Minister Mark Carney sent Mark Wiseman. Wiseman is a lawyer with degrees from Queen's University, the University of Toronto, and Yale. He spent three decades in law, business, and finance, most notably as CEO of the Canada Pension Plan Investment Board, one of the world's largest institutional investors. He is, by any conventional measure, exactly the kind of person you send when the stakes are existential and the other side knows how to exploit weakness.
Washington sent Pete Hoekstra.
Hoekstra is a 72-year-old former Michigan congressman whose most memorable prior ambassadorial moment was being publicly fact-checked by the Dutch government after he claimed Muslim mobs were burning politicians in the Netherlands and that the country had no-go zones — neither of which was true. He refused to fully retract the statements. He subsequently became Michigan Republican Party chair, left the party with approximately $1 million in debt according to party sources who spoke to the Globe and Mail, and is now the public face of American diplomacy toward its largest trading partner and closest ally, delivering annexation talking points and tariff threats to a country that sends more goods across the U.S. border every day than any other nation on earth.
The contrast between Wiseman and Hoekstra is not incidental. It is the clearest possible illustration of what American diplomacy has become under the Trump administration — an apparatus in which personal loyalty, ideological alignment, and proximity to the Trump family have replaced expertise, experience, and institutional knowledge as the primary qualifications for representing the most powerful nation on earth.
Nowhere is this more visible than in the Middle East, where the United States is simultaneously fighting a war with Iran, managing a fragile ceasefire, negotiating the future of Gaza, attempting to rebuild Syria, and maintaining relationships with Saudi Arabia, Jordan, Egypt, Turkey, Israel, and Lebanon — all at the same time, all in a region where miscalculation is measured in bodies.
The man leading American diplomatic efforts across this landscape is Steve Witkoff, a 69-year-old New York real estate developer who has been a close personal friend of Donald Trump for forty years — reportedly since the day he spotted Trump short on cash at a Manhattan deli and covered him. Witkoff serves simultaneously as Special Envoy to the Middle East and Special Envoy for Peace Missions, the latter role shared with Jared Kushner. His portfolio includes the Gaza hostage negotiations, the Iran nuclear talks, the Russia-Ukraine ceasefire, and Syrian reconstruction. He has no prior diplomatic experience. Trump described him at his swearing-in as someone who came into this work "with not a lot of experience in what he was doing here, but he had a lot of brilliance in business and great common sense." House Foreign Affairs Committee Democrats demanded an investigation into Witkoff's financial ties to World Liberty Financial — a crypto venture with growing connections to the very countries Witkoff negotiates with on behalf of the United States — after his financial disclosure from August 2025 showed he still had a financial interest in the company despite claiming to have divested.
In Jerusalem sits Mike Huckabee — former Arkansas governor, Baptist pastor, two-time failed presidential candidate, and Christian Zionist whose theology holds that modern Israel is the fulfillment of biblical prophecy. Huckabee has been U.S. Ambassador to Israel since April 2025. In February 2026, in an interview with Tucker Carlson, he was asked whether Israel had the right to land stretching from the Nile River to the Euphrates — a territory encompassing parts of Egypt, Sudan, Saudi Arabia, Iraq, Syria, Lebanon, and Jordan. "It would be fine if they took it all," Huckabee said. Fourteen countries issued formal condemnations. The administration was forced into diplomatic damage control, with senior officials reaching out to Arab states to clarify that this was Huckabee's personal position. Huckabee later called the remark hyperbolic. He did not apologize for it.
Huckabee had previously held a secret meeting with Jonathan Pollard — a former American intelligence analyst who spent 30 years in federal prison for passing classified documents to Israeli intelligence — at the U.S. Embassy in Jerusalem. The meeting was kept off his official calendar. The White House was not informed in advance. Democrats called Pollard a convicted traitor. Tucker Carlson, who had just interviewed Huckabee about the Nile to the Euphrates statement, called the conduct shocking behavior from a United States ambassador.
In Paris is Charles Kushner — Jared Kushner's father, Donald Trump's father-in-law, and a real estate developer who served federal prison time for tax evasion, witness tampering, and making illegal campaign contributions before receiving a presidential pardon from Trump in his first term. Kushner has been U.S. Ambassador to France since 2025. Within weeks of arriving, he published a letter in the Wall Street Journal addressed to French President Emmanuel Macron, blasting France's handling of antisemitism and linking Macron's recognition of a Palestinian state to an uptick in antisemitic incidents. France summoned him to the foreign ministry — a diplomatic expression of displeasure Paris had not employed against an American ambassador in years. Kushner's primary qualification for representing the United States to one of its oldest and most important allies is that his son is married to the president's daughter.
In Ankara and Damascus — simultaneously — sits Tom Barrack, serving as both U.S. Ambassador to Turkey and Special Envoy for Syria and Iraq, three of the most volatile diplomatic postings in the world consolidated into one man whose prior experience is private equity. Barrack was indicted in 2021 on charges of acting as an unregistered foreign agent of the United Arab Emirates and making false statements to federal investigators. He was acquitted by a jury in 2022 — a full acquittal — but the underlying questions about his Gulf relationships have never fully receded, and they shadow every aspect of his current role negotiating U.S. policy toward the very region where those relationships allegedly operated. Lawmakers from both parties have raised alarms about what they describe as his Turkey tilt — the perception among Turkish officials and American critics alike that Barrack is operating as Ankara's advocate inside American foreign policy rather than the other way around.
In New Delhi is Sergio Gor — born Sergey Gorokhovsky in Soviet Uzbekistan in 1986, age 39 — whose primary diplomatic credential before his appointment was co-founding a book publishing company with Donald Trump Jr. Before going to India he ran the White House Presidential Personnel Office, making him the gatekeeper who decided who got hired across the entire federal government. He is simultaneously the U.S. Ambassador to India and Special Envoy for South and Central Asia. To his credit, he helped produce an India-U.S. trade deal within weeks of arriving in New Delhi — a concrete outcome that even his critics acknowledged, and a reminder that personal access to the president can occasionally substitute for institutional expertise when the other side values proximity to power above all else.
And across 85 other posts — now closer to half of all American ambassadorial positions in the world — there is no one. The Trump administration recalled nearly 30 career diplomats at Christmas 2025, ordered home from Africa, Asia, Eastern Europe, and Latin America with no replacements named, leaving countries that depend on American diplomatic engagement suddenly facing empty embassies. The American Foreign Service Association called it institutional sabotage. Retired diplomat Tom Shannon said it was not standard by any prior measure. Marco Rubio — the Secretary of State who once called Trump a con man and who now executes his orders without public reservation — signed off on it and defended it as routine.
The cumulative picture is of an American diplomatic apparatus systematically hollowed out and refilled with people whose primary credential is personal relationship with one man. A televangelist who thinks Israel should stretch from the Nile to the Euphrates. A convicted felon whose son married the president's daughter. A private equity investor acquitted of acting as a UAE foreign agent. A real estate developer with a crypto conflict of interest. A book publisher who is 39 years old. And a Michigan congressman who lied about Dutch Muslim mobs and left his own party a million dollars in debt.
Against them sit the diplomats other countries send — career professionals, multilingual experts, people who have spent decades studying the specific country and relationship they are assigned to manage. Mark Wiseman at the Canadian embassy represents one end of that spectrum: a man whose qualifications for one of the world's most important bilateral relationships are genuinely exceptional.
Canada sends its best financial mind to Washington because it understands what is at stake. Washington sends Pete Hoekstra to Ottawa because he is available, loyal, and will deliver the message he is told to deliver without asking whether it makes sense.
That asymmetry is not a staffing problem. It is a foreign policy choice. And its consequences — the empty embassies, the summoned ambassadors, the Nile to the Euphrates statements, the secret meetings with convicted spies, the crypto conflicts of interest — are being felt in every region of the world where American credibility once served as the foundation of the international order.
Sources: Globe and Mail reporting on Pete Hoekstra and Michigan GOP debt, November 2025; Al Jazeera reporting on Huckabee Nile to Euphrates interview, February 2026; NBC News reporting on Huckabee-Pollard meeting, November 2025; Jerusalem Post reporting on Charles Kushner and France, August 2025; Jewish Insider reporting on Tom Barrack and Turkey, February 2026; House Foreign Affairs Committee letter on Steve Witkoff conflicts of interest, January 2026; UPI and Washington Post reporting on ambassador recalls, December 2025; American Foreign Service Association statements; Ballotpedia ambassadorial appointment data, March 2026; Global News reporting on Mark Wiseman appointment, December 2025.