Being Trump’s family and acquaintance, there was just one easy step to turn Jared Kushner and Steve Witkoff from real estate guys into “international grade” negotiators. Today, the pair’s competency to conduct diplomatic negotiations is a subject of intense debate, largely split between supporters who view them as effective "dealmakers" and critics who cite a lack of traditional expertise and the failure of key initiatives.
If we begin with Jared Kushner, his job in the first Trump administration (2017–2021), was to put together the Abraham Accords, that were meant to normalize relations between Israel and several Arab nations. In the second term (2025–present), he has worked on Gaza, Russia/Ukraine, and Iran, and was appointed as a Special Envoy for Peace when Trump was still dreaming of the Nobel Prize.
He doesn’t strike me as the sharpest tool in the shed. One key asset of Kushner is that he loves to multitask and conduct his real-estate business while negotiating diplomatically for his father in law. Obviously, his MAGA supporters think he’s a "world-class negotiator" with a deep understanding of Middle Eastern power dynamics.
Smarter critics, however, argue his diplomatic efforts—particularly regarding Iran—have been botched due to a lack of technical expertise, resulting in increased conflict rather than peace, plus have been clouded by his extensive business ties with Persian Gulf states, from which his firm Affinity Partners received funding. Talk about turbo-charged conflicts of interest!
As for Steve Witkoff, he’s first and foremost a New York real estate developer with no formal foreign policy or diplomatic training before 2025, Witkoff was appointed as Special Envoy to the Middle East and for Peace Missions. He was tasked with mediating the Gaza war, the Russia-Ukraine conflict, and negotiations with Iran.
Trump’s lapdog Rubio, credits him with employing innovative methods to advance US interests. He is described as a "tough" negotiator who focuses on understanding what the other side wants, similar to his business career, meaning that to him, diplomacy is just like selling houses, apartments and commercial properties.
This is precisely what makes cleared-eye critics argue that Witkoff "mistook diplomacy for a real estate deal," citing his "amateurish" handling of complex, technical issues, such as nuclear enrichment. He is criticized for adopting pro-Russian positions in negotiations, failing to grasp diplomatic protocol, and, along with Kushner, being seen by some as "Israeli assets" influencing the US into war and unconditionally supporting Israel rather than being a neutral party.
The pair is representative of what could be called “Transactional Diplomacy”. Both men treat high-stakes diplomacy as a business transaction, prioritizing personal relationships and "gut instinct" over traditional, bureaucratic, state-department-led negotiation methods.
Trump supporters see their strength as their direct, trusted relationship with the President, allowing them to act with authority and speed that career diplomats cannot. But while they helped secure a 2025 ceasefire/hostage exchange in Gaza, their broader negotiations, particularly with Iran, have been linked to an escalation in regional violence.
In a next blog, will see if JD Vance is any better for that kind of diplomatic negotiations...