Trump's Amateur Diplomats Struggle to Broker Complex Deals

Inexperienced negotiators and shifting, contradictory objectives undermine U.S. efforts to resolve conflicts in Ukraine, Gaza, and Iran.

Apr. 18, 2026 at 4:33pm

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A fragmented, abstract painting depicting a negotiating scene with shadowy, overlapping figures in muted tones, conveying the disjointed and ineffective nature of U.S. diplomatic efforts.The chaotic, amateurish nature of U.S. diplomacy under Trump undermines America's ability to broker deals on global conflicts.NYC Today

The Biden administration's reliance on amateur diplomats like Steve Witkoff and Jared Kushner, rather than seasoned professionals, has hampered U.S. efforts to broker ceasefires and peace deals in Ukraine, Gaza, and Iran. Coupled with President Trump's shifting and contradictory negotiating objectives, the amateurism of the U.S. delegation has doomed recent talks, according to columnist Andreas Kluth.

Why it matters

The failure of these diplomatic efforts has serious geopolitical consequences, as the U.S. struggles to influence the course of major global conflicts. It also reflects a broader trend of Trump administration officials sidelining career diplomats and foreign policy experts in favor of political allies and family members, undermining American credibility on the world stage.

The details

Kluth argues that the U.S. negotiating team in Islamabad, led by Vice President JD Vance and including real estate tycoon Steve Witkoff and Trump son-in-law Jared Kushner, lacked the expertise and experience to effectively engage with their Iranian counterparts. Witkoff in particular was criticized for relying on Kremlin interpretations during his shuttle diplomacy with Russia over the Ukraine conflict, while Kushner and Vance struggled to understand the technical details of the Iranian nuclear program.

  • The U.S. and Iran held talks in Islamabad in early 2026.
  • The Trump administration launched military strikes against Iran in February 2026.

The players

Steve Witkoff

A real estate tycoon from New York who has been friends with Trump for decades, but had no prior diplomatic experience before joining the second Trump administration as a 'special envoy' handling negotiations with Russia, Iran, and other global conflicts.

Jared Kushner

Trump's son-in-law, who helped broker the Abraham Accords in the first Trump term but was tasked with handling negotiations on Ukraine, Gaza, and Iran in the second term, despite lacking expertise in those areas.

JD Vance

The vice president, who was put in charge of the U.S. delegation to the Islamabad talks with Iran, despite being consistently opposed to foreign adventurism and the Iran war in particular.

Marco Rubio

The secretary of state and national security adviser, who has been sidelined from the major diplomatic efforts in Ukraine, Gaza, and Iran, despite his political survival skills and the president's ear on issues like Venezuela and Cuba.

Donald Trump

The president, whose shifting and contradictory negotiating objectives have undermined the ability of even skilled diplomats to reach successful agreements, while he has instead relied on political allies and family members to lead key talks.

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What they’re saying

“The amateurism is a problem all by itself, and is part of Trump's full-bore assault against professionalism across government.”

— Andreas Kluth, Bloomberg Opinion columnist

“Veterans of traditional diplomacy such as Aaron David Miller and Daniel Kurtzer give Witkoff and Kushner an F and consider the administration's diplomatic process a 'hot mess.'”

— Andreas Kluth, Bloomberg Opinion columnist

“If it turns into disaster (and it's well on the way), Vance could look prescient. That doesn't sit well with the boss.”

— Andreas Kluth, Bloomberg Opinion columnist

What’s next

The judge in the case will decide on Tuesday whether or not to allow Walker Reed Quinn out on bail.

The takeaway

This case highlights growing concerns in the community about repeat offenders released on bail, raising questions about bail reform, public safety on SF streets, and if any special laws to govern autonomous vehicles in residential and commercial areas.