Rather than relying on diplomats with the necessary negotiating skills and background to engage with Iranian counterparts — who, even he admits, are “great negotiators” — Trump has relied on friends and family who lack the required experience and know-how.
The president, his son-in-law Jared Kushner and his friend and Special Envoy to the Middle East Steve Witkoff are all convinced their private sector experience as dealmakers make them perfect diplomats. But the skills needed for those two jobs are very different — and not easily transferable.
In the private sector, dealmakers settle on the broad points of an agreement, leaving the details to lawyers. But in diplomacy, strategic and historical context matter — as does knowledge of what drives the other side, which is very different than simply making a buck.
We can see all this in Witkoff and Kushner’s go-to approach: putting down a term sheet, or rather a multi-point plan — 28 points for Ukraine, 20 for Gaza, 15 for Iran — and then trying to bamboozle the other side into accepting it. Meanwhile, the points are often vague, open to multiple interpretations and almost always divorced from the context of the conflict they seek to address.
The idea is that if one side “holds the cards,” the other side must fold. But that’s not how diplomacy works.
In Ukraine, the 28 points were mainly drawn up by Russia, and were roundly rejected by Kyiv. Then a new 19-point plan worked out with Ukraine was, predictably, rejected by Moscow. Today, the much-heralded negotiations that were supposed to end the war in one day have been suspended, and the conflict has entered its fifth year.