Yale historian Timothy Snyder has a clear diagnosis of why U.S. diplomacy on Ukraine is failing, and the problem starts in Washington. The entire diplomatic process has been handed to two men without diplomatic training: the president's son-in-law and the president's friend. Both tracks have already produced documented failures, in Ukraine and in Iran.
Two Men, Zero Diplomats
Jared Kushner and Steve Witkoff are now the primary U.S. envoys across three of the world's most consequential negotiations: the Russia-Ukraine ceasefire talks, the Iran nuclear discussions, and the Gaza situation. Neither has a background in diplomacy, international law, or security policy. In a March 2026 review, Foreign Policy gave them an F.
On Iran, the situation was stark. The Iranian Foreign Minister reportedly had to explain to Witkoff the stages of nuclear fuel production and the difference between an enrichment facility and a reactor. In April, Vice President Vance left talks in Islamabad with no agreement. Witkoff and Kushner privately told Trump it would be "difficult, if not impossible" to reach a deal with Iran.
On Ukraine, the pattern repeated. U.S. negotiators pressed Kyiv to relinquish strategically valuable territory to Russia while showing minimal interest in the nuances of the conflict. Snyder described what was presented as a peace plan as "more accurately described as a plan to intensify the war to the profit of a few Russians and Americans."
The Structural Argument
Snyder's diagnosis goes beyond personnel. When the organizing principle of U.S. foreign policy shifts from national interest to personal convenience, the people in the room matter less than the incentive structure driving them. Witkoff coordinates directly with Putin's economic envoy Kirill Dmitriev, a relationship that raises questions about whose interests are being served in negotiations billed as American-led.
Snyder describes the overall approach as "deliberate and characteristically Russian unreality," a negotiating environment designed to confuse rather than resolve, where the appearance of diplomacy serves as cover for the absence of it.
Snyder's published analysis makes clear the current arrangement is not simply incompetence, but "openly courting national and global catastrophe." Corruption, he argues, makes "national interests irrelevant" — and when national interests become irrelevant, what fills the vacuum is personal financial and political calculation.
What Ukraine Sees
Ukraine has grown openly skeptical of U.S. mediation. The calculation in Kyiv is that the people across the table have not demonstrated that they understand the conflict, the history, or the stakes. Snyder, who serves as a UNITED24 ambassador and has met directly with President Zelenskyy, is not an outside observer: he is embedded in the policy conversation and documents what he describes as a policy operating on personal financial and political convenience, dressed up as diplomacy.
Sources
- Trump Troubleshooters Witkoff and Kushner Get an F in Diplomacy -- Foreign Policy, March 2026
- Timothy Snyder: Russian Unreality and American Weakness -- Snyder Substack
- The Putin-Witkoff Plan Worsens the War -- Snyder Substack
- It's Not Working: Diplomats Fear Trump's Iran Envoys Are in Over Their Heads -- Time, April 2026
- America's Problem With Diplomacy Predates Trump -- Foreign Policy, April 2026
- Ukraine and Russia Are Souring on U.S. Negotiations -- Foreign Policy, May 2026
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