Reports have emerged about President Donald Trump’s inclination to assign his envoy to the Middle East, Steve Witkoff, to follow the Iran file— a move that carries profound strategic implications in light of significant global and regional shifts following Trump’s return to the White House in his second term. The decision to assign Witkoff to handle the Iran dossier, which was disclosed by the Financial Times on January 23, 2025, citing sources in Washington, conveys several messages that can be interpreted within the context of U.S. policy toward Iran, most notably the combination of diplomacy and pressure in dealing with Tehran. Although there are opportunities for Witkoff and Trump’s team to succeed in their mission, there are also significant challenges that may complicate this task.
Diplomacy and Pressure:
Trump’s choice to appoint Witkoff to manage the Iran file illustrates the continuation of Washington’s hardline approach towards Tehran, while simultaneously attempting to explore alternative diplomatic avenues before resorting again to escalating sanctions or military intervention against Iran. The significance of this choice can be summarized as follows:
Testing Diplomacy First: One of the key messages of this appointment is to assess the potential for achieving tangible results through diplomacy, contrasting with the “unilateral pressure” policy adopted by the U.S. administration during Trump’s first term (2017-2021). The direction to appoint a special envoy for a complex issue like Iran reflects Trump’s recognition that diplomacy can sometimes be an effective tool for achieving foreign policy goals, even in the face of adversaries. In this regard, the initiative to appoint Witkoff can be seen as a signal of Trump’s administration’s willingness to open informal communication channels with Tehran, or at least to test the viability of diplomacy in resolving some contentious issues, such as Iran’s nuclear and missile programs and its regional influence.
Integration of Diplomacy and Pressure: Despite the apparent diplomatic implication of appointing a special envoy, it cannot be overlooked that this move may be part of a broader strategy that combines diplomacy and pressure. This means that the current U.S. administration may wish to give diplomacy a chance but within the framework of economically, politically, and diplomatically constraining Iran, which enhances the envoy’s stature as a strong negotiator. From this perspective, the goal of appointing Witkoff is not only to seek a diplomatic settlement with Tehran but also to bolster the U.S. position in any upcoming negotiations by keeping sanctions and pressures in place. Trump revealed this sentiment on February 4, declaring that he plans to resume the “maximum pressure” policy on Iran due to its “attempts to develop nuclear weapons,” although he expressed hope that such a policy wouldn’t be necessary.
Role of Economic Diplomacy: A significant aspect of Witkoff’s anticipated appointment, given his extensive economic background, is the potential utilization of “economic diplomacy” in dealing with Iran. Trump has always emphasized economic matters and employs sanctions as a primary tool for pressuring adversaries. Thus, selecting Witkoff may signify a step towards achieving some form of economic settlement with Iran, especially in light of the economic crises Tehran faces due to American sanctions.
Available Opportunities:
Acknowledging the challenges faced by Witkoff and Trump’s team regarding the Iran file, there are available opportunities that may aid him in his mission, including:
Trump’s Desire to End Wars: Witkoff played a pivotal role in negotiating a ceasefire agreement between Israel and Hamas in the Gaza Strip, which enhances his chances of successfully managing the Iran file and avoiding military confrontation, especially given the Trump administration’s plans and promises to end wars in the Middle East and the world. Thus, it is expected that Witkoff, with the assistance of his deputy, Morgan Ortagus, will explore the possibility of reaching a diplomatic agreement with Iran while maintaining the ceasefire in Gaza.
Witkoff’s Economic Background: Witkoff’s substantial experience in economic negotiations may provide an advantage in dealing with Iran, particularly if the Trump administration relies on economic diplomacy as a pressure tool or part of a confidence-building strategy. Given the economic crisis faced by Iran due to American and international sanctions, Witkoff may seek to present economic solutions on the table, such as easing sanctions or allowing commercial agreements in exchange for concessions from Iran.
Experience in Using Sanctions: The United States has extensive experience in using economic sanctions as a pressure tool in foreign policy, a background that Witkoff can leverage in dealing with Tehran. American sanctions have severely harmed the Iranian economy, leading to a significant depreciation of the local currency and increased unemployment and inflation rates. Consequently, such economic pressures may compel Iran to return to the negotiation table, which Witkoff can utilize to reach agreements that advance U.S. interests.
Role of Allied Countries: U.S. allied nations in the region, particularly Israel, play a critical role regarding Iran, consistently opposing its nuclear program and pressuring Washington to take decisive steps to halt it. Witkoff could benefit from these relationships to strengthen Washington’s position in any negotiations with Tehran. If he successfully builds regional consensus around the Iranian issue, it could facilitate progress on addressing Tehran’s nuclear and missile programs.
Intertwined Challenges:
Witkoff’s mission regarding the Iran file represents one of the most significant challenges he may encounter in his diplomatic career, due to the complexities of the current regional landscape and the protracted enmity between Washington and Tehran. Although Witkoff possesses substantial experience in economic and negotiation fields, his potential dealings with the Iran file may face several intertwined challenges, including:
Lack of Mutual Trust: One of the most significant challenges for Witkoff and Trump’s team is the absence of mutual trust between the United States and Iran. Since the outbreak of the Iranian revolution in 1979, the relations between the two countries have been characterized by continuous tension, heightened by the U.S. withdrawal from the nuclear agreement in 2018 during Trump’s first term. This obstacle complicates the Trump administration’s efforts to find common ground for starting negotiations with Tehran. On its part, Iran is skeptical of U.S. intentions and believes that Washington seeks to overthrow its regime or at least weaken it; therefore, convincing the Iranian leadership that it would benefit from any new negotiations or gain real advantages will be challenging.
Iranian Influence in the Region: Iran maintains a network of regional influence through its support for armed groups in several Arab countries, such as Hezbollah in Lebanon, the Houthis in Yemen, and armed factions in Iraq. Although this Iranian axis has waned in light of the outcomes of the Israeli wars on Gaza and Lebanon and the accompanying escalation on several regional fronts, as well as the downfall of Bashar al-Assad’s regime in Syria, any U.S. move to exert further pressure on Iran may provoke violent responses from Iran-backed groups, complicating Witkoff’s mission. While these groups are weaker compared to pre-October 7, 2023, they still represent a challenge to Washington, as they are leverage for Iran to use against the U.S. and its allies in the region.
Influence of Russia and China: In addition to the United States, other international powers play significant roles in the Iranian dossier, such as Russia, which supports Tehran in various regional files and views it as a strategic partner in the Middle East. Similarly, China maintains strong trade and economic ties with Iran and considers it part of the “Belt and Road” initiative. The presence of these international powers undoubtedly complicates the U.S. ability to impose its will unilaterally on Iran. Witkoff may find himself needing to engage with these powers as part of the U.S. strategy toward Tehran. Any attempt to impose a mix of economic or political isolation on Iran may meet resistance from Russia and China, who may perceive U.S. sanctions on Tehran as threats to their interests.
American Divisions on Iran: There exists a division within the United States between Republicans and Democrats regarding how to approach Iran. While Republicans advocate a firm stance against Tehran and call for the continuation of the “maximum pressure” policy, Democrats pursue a more flexible diplomatic path and seek a return to the nuclear agreement signed in 2015. This division could render Witkoff’s task more challenging, as he may be compelled to balance internal pressures and the differing inclinations of congressional members.
Economic Situation in Iran: The state of the Iranian economy may simultaneously pose challenges and opportunities; although Iran suffers from economic problems due to American sanctions, the Iranian leadership may find a motivation for “resistance” in these difficulties rather than a reason for concessions. Historically, Iran has shown an ability to adapt to economic pressures, turning them into a driver to enhance its internal economic structure and self-reliance. Therefore, Witkoff may need innovative strategies to convince Iran that negotiation and compromise are preferable to continued “resistance” to sanctions. He might also need to consider how to offer economic incentives to Tehran in exchange for concessions regarding its nuclear and missile programs or for curtailing its interventions in other regional countries’ affairs.
Potential Scenarios:
In light of the move to assign Witkoff to the Iran file, some scenarios for U.S. policy under Trump toward Tehran can be anticipated:
- Pressure with Diplomatic Flexibility: The most likely scenario appears to be the continuation of the “maximum pressure” policy while allowing some diplomatic flexibility to open communication channels with Iran. The current Trump administration may choose a strategy that relies on sanctions and economic pressures, combined with offering some economic incentives in exchange for concessions from the Iranian side.
- Possibility of a Temporary Agreement: If diplomatic efforts led by Witkoff prove successful, the United States and Iran might reach a temporary agreement, including the freezing of some Iranian nuclear activities in exchange for partial sanction relief.
- Return to Open Confrontation: Should diplomatic efforts falter and tensions escalate between Washington and Tehran, the Trump administration may revert to a more provocative approach, including imposing tougher sanctions or even considering limited military options. However, this option remains complex and requires a degree of American daring due to the significant regional risks posed by any military confrontation with Iran.
In conclusion, the direction of the Trump administration to assign Witkoff, as part of a team, to handle the Iran file reflects not only the complexity and importance of this issue in American foreign policy but also Washington’s desire to explore new pathways for addressing this complex file by testing the possibilities of diplomatic solutions alongside the continuation of “maximum pressure.”
