President Trump's unconventional diplomatic point man is heading to Rome for a second round of high-stakes nuclear talks with Iran, despite facing fierce criticism over his lack of diplomatic experience and recent policy missteps that have alarmed allies and experts alike.
Steve Witkoff, a billionaire real estate developer with no prior diplomatic experience, has emerged as President Donald Trump's de facto foreign policy czar, simultaneously juggling negotiations with Russia over Ukraine and Iran over its nuclear program. His upcoming talks in Rome represent a critical juncture in U.S. efforts to forge a new nuclear agreement with Tehran, even as questions mount about his qualifications and approach to sensitive international diplomacy.
Key Developments in Witkoff's Diplomatic Mission
From Real Estate Deals to Global Diplomacy
Witkoff's unlikely journey to becoming America's chief negotiator with adversaries like Russia and Iran began in the 1980s, when he first met Donald Trump while working at the New York real estate law firm Dreyer & Traub. According to multiple sources, Witkoff got into real estate because he wanted to emulate Trump, eventually building his own successful development company.
"As Witkoff tells it, he got into real estate because he wanted to be like Trump, meeting him for the first time as a lawyer at the firm Dreyer & Traub," Bloomberg1 reported.
Their decades-long friendship has now propelled Witkoff into a position that would typically be filled by career diplomats or experienced foreign policy experts. Despite being officially designated as the U.S. Special Envoy to the Middle East, Witkoff has rapidly expanded his portfolio to include serving as Trump's primary channel to Russian President Vladimir Putin and leading nuclear negotiations with Iran.
Iran Nuclear Negotiations: Controversial Statements and Quick Reversals
Witkoff's handling of the Iran nuclear issue has been particularly contentious. Earlier this week, he created a diplomatic firestorm when he suggested on Fox News that the U.S. might accept a deal allowing Iran to continue enriching uranium up to 3.67 percent, essentially reverting to a framework similar to the Obama-era nuclear deal that Trump previously condemned.
"On Monday he announced that the key to any deal with Tehran was that they do not need to enrich past 3.67 per cent," The Telegraph2 reported. "But the fatal flaw in the 2015 Obama nuclear deal with Iran which Donald Trump rightly ripped up in 2018 as the worst deal ever was allowing any enrichment, which gives the mullahs a pathway to a nuclear weapon."
Facing immediate backlash, Witkoff quickly reversed course the following day, declaring that the U.S. was demanding Iran completely dismantle its enrichment program. This abrupt policy shift prompted concerns about mixed messaging and undermined confidence in the negotiation strategy.
As Witkoff prepares for this weekend's talks in Rome, he is working to refine a framework that aligns with "the President's objective of having Iran dismantle its nuclear program," according to a spokesperson, who added that Witkoff "is working to resolve our differences with Iran through dialogue and diplomacy, if that is possible," Politico3 reported.
Global Reactions to Witkoff's Diplomatic Role
Israeli Concerns and Outreach Efforts
Israeli officials have expressed significant apprehension about Witkoff's approach to Iran. In an effort to address these concerns, he met with Ron Dermer, a top aide to Israeli Prime Minister Benjamin Netanyahu, and Mossad Director David Barnea in Paris on Thursday to brief them on the upcoming talks.
The meeting came amid growing Israeli anxiety about potential U.S. concessions to Iran. Israeli leaders have consistently advocated for a harder line against Tehran's nuclear ambitions, viewing any enrichment capacity as an existential threat.
Skepticism Among Republican Foreign Policy Experts
Within Republican circles, there is widespread skepticism about both Witkoff's diplomatic capabilities and Iran's willingness to negotiate in good faith. When Politico surveyed seven administration officials, conservative foreign policy experts, and GOP senate aides about Witkoff's chances of securing a deal, the responses ranged from "probably not" to a "resounding no."
"The problem I've heard so far is that they're not serious about an agreement," said Fred Fleitz, a former chief of staff to then-national security adviser John Bolton, referring to Iran. "But maybe this weekend they'll say something else," Politico3 reported.
Expert Insights on Witkoff's Diplomatic Approach
Diplomatic Inexperience as a Liability
Foreign policy experts have raised serious concerns about Witkoff's lack of diplomatic experience and apparent naivety in dealing with adversaries. His previous diplomatic efforts, including negotiations with Hamas over hostage releases, have faced criticism after he publicly admitted to being "duped" by the terrorist organization.
"It's not me asserting Witkoff was duped by Hamas. That's what Witkoff himself said: 'I thought we had an acceptable deal. I even thought we had an approval from Hamas. Maybe that's just me getting duped,'" The Telegraph2 reported.
His comments about Russian President Vladimir Putin have been similarly controversial. Witkoff has described Putin as a "super smart guy" and stated, "I don't regard Putin as a bad guy... I liked him... I thought he was straight up with me." He has also repeated Russian talking points about referendums in occupied Ukrainian territories, claiming that "the overwhelming majority of the people have indicated that they want to be under Russian rule," despite international consensus that these votes were illegitimate.
Technical Challenges of Nuclear Negotiations
Beyond questions of diplomatic skill, experts highlight the immense technical complexity of nuclear negotiations. The original Iran nuclear deal (JCPOA) required years of detailed work by large teams of specialized experts. By contrast, Trump has given Witkoff just 60 days to produce results, with the possibility of extensions only if clear progress is demonstrated.
"The Obama-era Iran nuclear deal took many experts to craft and years to hash out," Politico3 noted, underscoring the challenge facing Witkoff's small team operating under tight deadlines.
Future Implications for U.S. Foreign Policy and Global Security
Short-Term Impact on Nuclear Negotiations
The immediate stakes of Witkoff's diplomatic mission are extraordinarily high. Iran's nuclear program has advanced significantly since the U.S. withdrawal from the JCPOA in 2018, with the country now capable of producing enough enriched uranium for a nuclear weapon in as little as a month, according to some estimates.
"Iran is capable of enriching enough uranium to build one nuke a month," The Hill4 reported, highlighting the urgency of effective diplomatic action.
Critics argue that Witkoff's inconsistent statements and apparent willingness to make early concessions have already undermined the U.S. negotiating position. "By not declaring a sense of urgency, he is effectively giving Iran time," one analyst told The Hill.
Long-Term Consequences for U.S. Diplomatic Credibility
The broader implications of Witkoff's unconventional diplomacy extend beyond the Iranian nuclear issue. His simultaneous involvement in negotiations with Russia over Ukraine and efforts to resolve the Gaza conflict represent a significant departure from traditional diplomatic practice, where specialized teams with regional expertise typically handle discrete issues.
This approach raises questions about the coherence of U.S. foreign policy under Trump's second term and could affect America's diplomatic credibility with both allies and adversaries. Critics suggest that relying on personal relationships rather than institutional expertise risks making U.S. foreign policy unpredictable and potentially ineffective.
A High-Stakes Diplomatic Gamble
As Steve Witkoff heads to Rome for his second round of talks with Iranian officials, he carries not only the weight of America's nuclear security interests but also growing questions about President Trump's unconventional approach to diplomatic appointments. Will Witkoff's real estate dealmaking skills translate to the complex world of nuclear nonproliferation, or does his rapid ascent represent a diplomatic experiment that could have serious consequences for global security?###
