The Real Estate Envoys: How Witkoff and Kushner Earned an F in Diplomacy
Two veteran diplomats grade Trump's unconventional negotiators on three simultaneous crises—and find catastrophic failure beneath the dealmaking veneer.
Two former U.S. diplomats writing in Foreign Policy have assigned Steve Witkoff and Jared Kushner a failing grade for their handling of three historic conflicts—Ukraine, Iran, and Gaza—concluding that until the duo “produce something consequential, we’d give them an F.”
The assessment comes from Aaron David Miller, a senior fellow at the Carnegie Endowment for International Peace and former State Department Middle East analyst, and Daniel Kurtzer, former U.S. ambassador to Egypt and Israel who now teaches at Princeton. Their core criticism: there is “no precedent in the annals of U.S. diplomacy for a president turning the efforts to resolve three historic conflicts simultaneously over to his best friend and his son-in-law.”
The verdict lands as the United States, Israel, and Iran remain at war, Russia and Ukraine continue fighting, and the Gaza ceasefire collapses. The authors argue the negotiating structure President Trump created “is a hot mess,” pointing to fundamental inexperience that has turned high-stakes diplomacy into what critics call amateur hour with nuclear stakes.
The Credentials Gap
Steve Witkoff, a billionaire real estate developer worth $2 billion, had “limited formal diplomatic experience” before Trump appointed him Special Envoy to the Middle East in November 2024. His background consists entirely of making his fortune in New York real estate, with Senator Thom Tillis (R-NC) noting that while “Kushner and Witkoff are very accomplished businesspeople,” they are “not subject to Senate confirmation, and they’re not subject to oversight.”
| Credential | Career Diplomats | Witkoff/Kushner |
|---|---|---|
| Foreign Policy Training | Decades in Foreign Service | None |
| Senate Confirmation | Required for ambassadors | Not required for envoys |
| Conflicts Screening | Rigorous ethics reviews | Business ties retained |
| Regional Experience | Years in-country assignments | Real estate transactions |
Kushner himself told one of the Foreign Policy authors during Trump’s first term “that he wasn’t interested in hearing about any previous agreement or negotiation,” later announcing “there was nothing to learn from the previous efforts to negotiate peace between Israel and the Palestinians.” Witkoff admitted his naivety in a March interview with Tucker Carlson: “I underestimated the complications in the job, that’s for sure. I think I was a little bit quixotic in the way that I thought about it.”
Pattern of Failure Across Three Fronts
The recent collapse of U.S.-Iran negotiations in Oman and Switzerland preceded a rush to war, exposing what the diplomats characterize as either incompetence or deliberate deception. Miller and Kurtzer conclude that “Witkoff and Kushner appeared to sense what Trump wanted and, at his direction, played out a deception strategy by engaging with Iran and making unrealizable demands while Trump and Israeli Prime Minister Benjamin Netanyahu were plotting war.”
On Ukraine, “Trump has directed Witkoff and Kushner to press Zelensky to relinquish a strategically valuable part of his country’s territory,” with the negotiators showing “minimal interest in the nuances of the conflict and its wider implications for trans-Atlantic and global security.” Witkoff’s comments about Russia betrayed stunning inexperience: “I don’t regard Putin as a bad guy,” he told audiences, describing a man who “launched an illegal, unprovoked invasion and has massacred thousands of Ukrainians.”
In Gaza, the authors describe Witkoff and Kushner’s efforts as “even more pronounced” as a charade, with Trump’s “20-point peace plan, beginning with a cease-fire, followed by a series of performative actions, not serious negotiations.”
The Structural Dysfunction
A core problem identified in the Foreign Policy analysis is Trump’s social media interference: “Whatever advantages that Trump’s Truth Social platform provide for him in domestic politics, it has become a tremendous liability in foreign policy,” as “Trump is blustering and bloviating on social media” while his envoys negotiate, leaving America’s “negotiating partners simply don’t know what to believe.”
The authors contrast Witkoff and Kushner’s approach with Henry Kissinger’s 1970s achievements—the opening to China, Paris peace accords on Vietnam, and three disengagement accords following the 1973 Arab-Israeli war—noting that Kissinger possessed deep expertise and decades of experience the current envoys lack entirely.
Miller and Kurtzer identify multiple structural deficiencies: “a mercurial president, a lack of strategy, strong biases, amateur and over-extended negotiators, and a heavy dose of self-dealing add up to failure,” warning that “under Trump’s failed leadership, as well as Witkoff and Kushner’s failed negotiations, the situation has only worsened.”
Witkoff’s operational approach raises red flags for professionals. According to Foreign Policy, he “excluded U.S. State Department and National Security Council experts from his meetings, sometimes relying solely on Kremlin-supplied interpreters, which is an appalling breach of diplomatic due diligence.”
Conflicts of Interest at Scale
Beyond inexperience lies a web of financial entanglements that would disqualify conventional diplomats. Kushner’s investment firm Affinity Partners received $2 billion from Saudi Arabia’s sovereign wealth fund, while Witkoff co-founded World Liberty Financial, a cryptocurrency company with his sons and Trump family members, which secured a $2 billion investment from a UAE-backed firm.
According to Chicago Tribune columnist Elizabeth Shackelford, Kushner’s firm holds “billions of dollars in investments from investment funds controlled by the governments of Saudi Arabia, Qatar and the United Arab Emirates,” while “World Liberty Financial secured a $2 billion investment from a UAE-backed government firm around the same time that Witkoff successfully advocated for the export of advanced artificial intelligence chips to the UAE.”
When questioned about these arrangements on 60 Minutes, Kushner defended them: “What people call conflicts of interests, Steve and I call experience and trusted relationships that we have throughout the world.”
Bipartisan Alarm
Even Republican Senator Thom Tillis questioned the arrangement, telling The Hill that putting “Kushner and Witkoff in charge of high-stakes foreign policy and national security negotiations ‘doesn’t make any sense.'” Republican Representative Don Bacon went further, writing that “for those who oppose the Russian invasion and want to see Ukraine prevail as a sovereign [and] democratic country, it is clear that Witkoff fully favors the Russians.”
“The negotiating structure that U.S. President Donald Trump has created to deal with conflict is a hot mess. There’s no precedent in the annals of U.S. diplomacy for a president turning the efforts to resolve three historic conflicts simultaneously over to his best friend and his son-in-law.”
— Aaron David Miller & Daniel Kurtzer, Foreign Policy
The diplomatic corps itself is hemorrhaging talent. According to CNN, an American Foreign Service Association survey found 98% of diplomats reported declining morale since January 2025, with 25% of the foreign service having “resigned, retired, seen their agencies dismantled, or been removed from their posts,” and a third considering early departure.
Eric Rubin, former AFSA president and retired career diplomat, warned that “the ambassadors who have been dismissed will mostly have to retire, which means the State Dept. will lose a large number of our most senior, experienced and accomplished professionals. This is bad for our diplomacy, bad for our national security, and bad for our influence in the world.”
What to Watch
The Witkoff-Kushner experiment represents more than personnel choices—it signals whether American statecraft can function without institutional expertise. As Miller and Kurtzer note, “It is not clear that any of these conflicts would have been amenable to a diplomatic solution under the best of circumstances,” but the administration’s approach has eliminated the possibility of finding out.
AFSA President John Dinkelman characterized the diplomat purge as “unprecedented,” calling it “a sabotage of the American diplomatic machine.” With over half of U.S. embassies now lacking confirmed ambassadors and negotiations on Ukraine, Iran, and Gaza producing no breakthroughs, the question is whether Trump will maintain confidence in his unconventional team or whether mounting failures will force a course correction.
As Reuters observed, sending the pair “to solve two entrenched conflicts ‘in a single day in Geneva’ has raised questions not only about whether they are overstretched and outmatched, but about their serious prospects for resolving either of the twin crises.” The F grade from seasoned diplomats suggests the answer is becoming uncomfortably clear.