Witkoff and Kushner Get an F in Diplomacy
Inexperienced and overextended, Trump’s envoys have failed on three fronts.
The recent failure of U.S.-Iran negotiations in Oman and Switzerland and the rush to war are painful reminders of just how hard it is to deal with Iran. But they also reveal that 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. Former U.S. National Security Advisor and Secretary of State Henry Kissinger pulled off a trifecta in the 1970s: the opening to China; the Paris peace accords on Vietnam; and three disengagement accords following the 1973 Arab-Israeli war. But suffice it to say that Steven Witkoff and Jared Kushner are no Kissinger. And when it comes to strategic thinking, Trump is no Richard Nixon.
There’s an upside, of course, for turning U.S. diplomacy over to Trump’s family and friends. And that’s the personal access and trust that mediators have with the boss and how that access allows them to gain entry to principal decision-makers. But the downsides, particularly the absence of adult supervision in the Oval Office, far outweigh those advantages. Trump’s three-ring negotiating plays are failing, and here’s why.
Strategic vacuum
U.S. policy in all three conflicts—Russia-Ukraine, Iran, and Israel-Palestine—is rudderless, with no overall strategy and little coordination between means and ends. Trump has shown a deep bias against Ukrainian President Volodymyr Zelensky and an equally deep unwillingness to press Russia, the clear aggressor in this conflict. Whatever minor pressures have been applied on Russian entities via sanctions pale in comparison to the pressure that Trump has put on Ukraine by having Europe pay for U.S. weapons for Ukraine and denying Kyiv long-range strike capability. U.S. negotiators are hamstrung by a president who is not willing to press Russian President Vladimir Putin to stop the war. On the face of it, Putin’s war aims make any deal almost impossible. And yet, Kushner and Witkoff, directed by Trump, have taken themselves out of the game by catering to Russia and refusing to use the formidable leverage that Trump has.
The current U.S.-Israeli attacks on Iran similarly lack a strategic focus. Trump and his spokespeople have been tripping over themselves trying to describe a reason that is significant enough to warrant initiating a war. Trump named regime change as the reason but has failed to mention it in his subsequent remarks, while U.S. Defense Secretary Pete Hegseth said it’s not regime change. Gen. Dan Caine, the chairman of the U.S. Joint Chiefs of Staff, talked about destroying Iran’s capacity to project its power abroad. Trump said Iranian missiles were poised to be launched against the United States, but military briefers said there was no evidence that Iran was planning to attack the country.
It is clear 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. In the run-up to both the June 2025 war with Iran and the current conflict, the Trump administration scheduled follow-up talks and even a trip by U.S. Secretary of State Marco Rubio to Israel when it knew war was imminent. An unwitting foreign minister from Oman found himself haplessly isolated in Washington the day before the United States went to war.
In Gaza, Witkoff and Kushner’s charade is even more pronounced. Trump’s success in forcing Israel to accept his 20-point peace plan, beginning with a cease-fire, has been followed by a series of performative actions, not serious negotiations. The so-called Board of Peace could be a potentially useful instrument to fundraise for Gaza; but without serious pressure on Hamas to begin demilitarizing and Israel to begin withdrawing, there won’t be any construction to fund in the Hamas-controlled zone. Netanyahu and Hamas clearly prefer the status quo.
Kushner’s presentation at this year’s World Economic Forum in Davos, Switzerland, of a day-after plan for Gaza was a fantastical, Disneyland-esque illusion about a society in which homelessness, food insecurity, and health trauma persist. There are no senior Palestinian representatives associated with the Gaza plan, no serious role for the Palestinian Authority, and no effort by the Trump administration to constrain Israel’s annexationist policies on the West Bank, let alone dislodge Israel from the more than 50 percent of Gaza that it currently occupies. The U.S. war with Iran will only ensure delays in implementation of Trump’s plan, leaving Gaza divided, dysfunctional, and sporadically violent.
No expertise, no process
Real-estate people are better suited than we to assess the ability of Witkoff and Kushner to make real-estate deals. As diplomats, with decades of experience between us, we are well-suited to conclude that this team is clearly uninformed or ignorant about the deep roots of the Israeli-Palestinian conflict, the overlapping nature of shared religious space, and the demands and needs of both sides. This partly is a real-estate deal, but it’s also so much more. In Trump’s first term, Kushner told one of us that he wasn’t interested in hearing about any previous agreement or negotiation; he later announced there was nothing to learn from the previous efforts to negotiate peace between Israel and the Palestinians. Kushner had more success with the Abraham Accords. But the Trump administration’s policy toward Palestinians was an abject failure. Indeed, Trump’s decision in his first term to disengage from the Palestinians and to put forward a one-sided plan that would have blessed Israel’s annexation of 30 percent of the West Bank—on top of the 78 percent of historic Palestine/Eretz Israel that Israel already controls—illustrated how divorced the diplomacy was from reality.
In Ukraine, Trump has directed Witkoff and Kushner to press Zelensky to relinquish a strategically valuable part of his country’s territory to an aggressor that has shown little inclination to abandon its long-standing aim of subjugating the entirety of Ukraine. Putin’s envoy, Kirill Dmitriev, has sought to entice the Trump administration with proposals for commercial deals in Russia that could benefit the business interests of Trump, his close advisors, and their families. The U.S. negotiators have shown minimal interest in the nuances of the conflict and its wider implications for trans-Atlantic and global security, preferring instead to push for a deal that rests on Ukrainian capitulation to Russia’s demands.
Similarly, in Iran, the Omani hosts and intermediators have stripped away the illusion that Witkoff and Kushner were negotiating in earnest. After Trump pulled out of the Joint Comprehensive Plan of Action (JCPOA) in 2018, his bar to achieve a new agreement became impossibly high to overcome. Iranians might have accepted limits on enrichment and intrusive inspections, but it was never in the cards to expect them to go to zero enrichment. Did Witkoff and Kushner seriously believe that Iran would find it credible to accept promises of free enriched uranium from the same president who broke the JCPOA? Witkoff’s interview with Fox shortly before the war commenced revealed his astonishment that Iran had not ”capitulated” to U.S. pressure.
Read More
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No discipline
Trump and his negotiators have shown no discipline in negotiations or strategic communications, either at home or abroad. On Gaza, Trump’s identification with Netanyahu’s goals and subordination to Israeli interests is a fatal flaw that has undercut most U.S. mediation efforts since the mid-1990s. There are two parties to the Israel-Palestine conflict, but Witkoff and Kushner have only tried to address Netanyahu’s interests.
Whatever advantages that Trump’s Truth Social platform provide for him in domestic politics, it has become a tremendous liability in foreign policy, particularly in these three negotiations. While Witkoff and Kushner are engaging with the Russians, Ukrainians, Israelis, and Omanis, Trump is blustering and bloviating on social media. As a result, the United States’ negotiating partners simply don’t know what to believe.
We know how difficult it is to conduct this kind of diplomacy, especially with leaders who are more invested in keeping their seats and adhering to ideologies, rather than ending conflicts. We’ve both been there and have experienced successes and failures. Thus, it’s an open question as to whether, if you brought back Kissinger, paired him with James Baker, and put a president with foreign-policy judgment and experience like George H.W. Bush in the White House, you could crack Russia and Ukraine, let alone solve the Iran and Israeli-Palestinian conflicts. No matter how talented the mediator, the parties to a conflict need to possess a shared urgency that a deal is desirable and possible, which would allow the mediator to use incentives and disincentives to move the parties toward an agreement.
However, 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 and account for why Witkoff and Kushner have been so unsuccessful in all three negotiations. It is not clear that any of these conflicts would have been amenable to a diplomatic solution under the best of circumstances. But under Trump’s failed leadership, as well as Witkoff and Kushner’s failed negotiations, the situation has only worsened. The United States, Israel, and Iran are at war; Russia and Ukraine remain at war; and Israel and Hamas may as well be. To be charitable, we might give Kushner and Witkoff an incomplete for the semester. But until they actually produce something consequential, we’d give them an F.
This post is part of FP’s ongoing coverage. Read more here.
Aaron David Miller is a senior fellow at the Carnegie Endowment for International Peace and a former U.S. State Department Middle East analyst and negotiator in Republican and Democratic administrations. He is the author of The End of Greatness: Why America Can’t Have (and Doesn’t Want) Another Great President. X: @aarondmiller2
Daniel C. Kurtzer is a former U.S. ambassador to Egypt and Israel. He teaches diplomacy and conflict resolution at Princeton University’s School of Public and International Affairs. X: @DanKurtzer
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