Recent reports suggest that U.S. President Donald Trump is considering assigning his Middle East envoy, Steve Witkoff, to oversee the Iran dossier. The move carries significant strategic implications, especially in light of the major shifts in the global and regional landscape following Trump's return to the White House for his second term.
According to the Financial Times on January 23, 2025, citing informed sources in Washington, the decision to give Witkoff responsibility over Iran diplomacy sends several messages that can be interpreted within the context of U.S. policy toward Iran. Chief among these is the combination of diplomacy and pressure in dealing with Tehran. While opportunities exist for Witkoff and the Trump team to succeed in this mission, challenges could complicate their efforts.
Diplomacy and Pressure
Trump’s decision to appoint Witkoff as part of his team to handle the Iran dossier underscores the continuation of Washington’s hardline approach toward Tehran. However, it also signals an attempt to explore alternative diplomatic avenues before resorting once again to escalating sanctions or military intervention against Iran. The key implications of Trump’s decision can be outlined as follows:
1- Testing the diplomacy-first approach:
A central message of this assignment is to test the possibility of achieving tangible results through diplomacy, in contrast to the "maximum pressure" policy adopted by the Trump administration during its first term (2017–2021). By appointing a special envoy to handle a complex issue like Iran, Trump appears to recognize that diplomacy can sometimes be an effective tool for achieving foreign policy goals, even when dealing with adversaries. In this context, Witkoff’s appointment can be seen as a signal of the Trump administration’s willingness to open informal channels of communication with Tehran, or at least to test the feasibility of diplomacy in resolving contentious issues such as Iran’s nuclear and missile programs and its regional influence.
2- Integrating diplomacy and pressure:
The appointment of a special envoy may suggest a diplomatic approach, yet it could be part of a broader strategy combining diplomacy and pressure. The current U.S. administration may want to give diplomacy a chance, but within the framework of economically, politically, and diplomatically constraining Iran. Such an approach would enhance the new envoy's position as a strong negotiator. From this perspective, appointing Witkoff serves not only to seek a diplomatic settlement with Tehran but also to strengthen the U.S. position in any future negotiations by maintaining sanctions and pressure. The Trump administration appears unlikely to abandon the "maximum pressure" policy entirely, instead potentially using it as leverage to impose its terms on Tehran. Trump revealed this stance on February 4, when he announced his intention to resume the "maximum pressure" policy on Iran due to its alleged attempts to develop nuclear weapons. However, he expressed hope that implementing such measures would not be necessary.
3- The role of economic diplomacy:
Another implication of Witkoff’s expected appointment, given his extensive economic background, is the potential use of "economic diplomacy" in dealing with Iran. Trump has always prioritized economic issues and used sanctions as a key tool for pressuring adversaries. Thus, the choice of Witkoff could be a step toward achieving some form of economic settlement with Iran, especially given the economic crises Tehran is facing due to U.S. sanctions.
Available Opportunities
While acknowledging the challenges Witkoff and the Trump team face in handling the Iran dossier, there are opportunities that could aid their success. These include:
1- Trump’s desire to end wars:
Witkoff played a pivotal role in brokering a ceasefire agreement between Israel and Hamas in the Gaza Strip, enhancing his chances of success in dealing with Iran and avoiding military confrontation. The achievement is particularly relevant given the Trump administration's plans and promises to end wars in the Middle East and beyond. As a result, Witkoff, with the assistance of his deputy Morgan Ortagus, is expected to explore the possibility of reaching a diplomatic agreement with Iran, as well as maintaining the Gaza ceasefire.
2- Witkoff’s economic background:
Witkoff’s extensive experience in economic negotiations could be an asset in dealing with Iran, especially if the Trump administration relies on economic diplomacy as a tool for pressure or confidence-building. Given Iran’s economic crisis, exacerbated by U.S. and international sanctions, Witkoff may seek to offer economic solutions, such as easing sanctions or allowing trade agreements, in exchange for concessions from Iran.
3- Experience in using sanctions:
The United States has a long history of using economic sanctions as a tool of foreign policy, and this experience could be leveraged by Witkoff in dealing with Tehran. U.S. sanctions have already inflicted significant damage on Iran’s economy, leading to a sharp decline in the value of its currency and rising unemployment and inflation rates. These economic pressures may push Iran back to the negotiating table, which Witkoff could exploit to reach understandings that serve U.S. interests.
4- The role of allies:
U.S. allies in the region, particularly Israel, which consistently opposes Iran’s nuclear program and pressures Washington to take decisive steps to halt it, play a crucial role in the Iran dossier. Witkoff could leverage these relationships to strengthen Washington’s position in any negotiations with Tehran. If he can build regional consensus on the Iran issue, it could help advance efforts to address Tehran’s nuclear and missile programs.
Intertwined Challenges
Witkoff’s mission to handle the Iran dossier is one of the most significant challenges he may face in his diplomatic career, given the complexity of the current regional landscape and the long-standing animosity between Washington and Tehran. Despite his extensive experience in economic and negotiation matters, his potential handling of the Iran dossier could encounter several intertwined challenges, including:
1- Lack of mutual trust:
A significant challenge facing Witkoff and the Trump team is the deep-rooted mistrust between the United States and Iran. Relations between the two nations have been characterized by persistent tension since the 1979 Iranian Revolution, with the situation further deteriorating after the U.S. withdrawal from the nuclear deal in 2018 during Trump's first term. Such an obstacle complicates the Trump administration's efforts to find common ground and initiate negotiations with Tehran.
Iran's skepticism towards U.S. intentions presents another hurdle, as Tehran believes Washington aims to overthrow or weaken its ruling system. Consequently, convincing Iranian leadership of potential benefits from new negotiations or the possibility of gaining tangible concessions will prove challenging for the Trump team.
2- Iran’s regional influence:
Iran wields significant 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. The Iranian axis has seen its influence wane in light of the outcomes of the Israeli war on Gaza and Lebanon, as well as the escalation on multiple regional fronts and the fall of Bashar Assad's regime in Syria. However, any U.S. move to increase pressure on Iran could provoke violent reactions from Tehran-backed groups, further complicating Witkoff's mission. While these groups have weakened compared to the pre-October 7, 2023, period, they still pose a challenge to Washington, remaining as potential tools Iran could use against the United States and its regional allies.
3- The influence of Russia and China:
In addition to the United States, other global powers play a significant role in the Iran dossier, such as Russia, which supports Tehran in various regional issues and considers it a strategic partner in the Middle East, and China, which has strong trade and economic ties with Iran and views it as part of its Belt and Road Initiative. The presence of these international powers could make it difficult for the United States to unilaterally impose its will on Iran. Witkoff may find himself compelled to engage with these powers as part of the U.S. strategy toward Tehran. Moreover, any attempt to economically or politically isolate Iran could face resistance from Russia and China, as they may view U.S. sanctions on Tehran as a threat to their interests.
4- Domestic U.S. divisions on Iran:
There is a divide within the United States between Republicans and Democrats on how to deal with Iran. While Republicans advocate for a firm stance against Tehran and call for the continuation of the "maximum pressure" policy, Democrats seek a more flexible diplomatic approach and a return to the 2015 nuclear deal. This division could make Witkoff’s mission more challenging, as he would need to balance internal pressures and the differing orientations of Congress members.
5- Iran’s economic situation:
Iran’s economic situation could represent both a challenge and an opportunity. While Iran is suffering from economic problems due to U.S. sanctions, its leadership may view these difficulties as a motivation for "resistance" rather than making concessions. Historically, Iran has demonstrated an ability to adapt to economic pressures, using them as a catalyst to develop its domestic economic infrastructure and self-reliance. Therefore, Witkoff may need innovative strategies to convince Iran that compromise and negotiation are preferable to continued "resistance." He may also need to consider offering economic incentives to Tehran in exchange for concessions on its nuclear and missile programs or a reduction in its interference in the affairs of other regional countries.
Potential Scenarios
In light of the decision to task Witkoff with the Iran dossier, several scenarios for the Trump administration’s policy toward Tehran can be envisioned:
1- Pressure with diplomatic flexibility:
The most likely scenario is the continuation of the "maximum pressure" policy combined with some diplomatic flexibility to open channels of communication with Iran. The current Trump administration may choose a strategy that relies on sanctions and economic pressure while offering some economic incentives in exchange for Iranian concessions.
2- Possibility of a temporary agreement:
If diplomatic efforts led by Witkoff succeed, the United States and Iran may reach a temporary agreement that includes freezing some of Iran’s nuclear activities in exchange for a partial easing of sanctions.
3- Return to open confrontation:
If diplomatic efforts fail and tensions between Washington and Tehran escalate, the Trump administration may return to a more confrontational approach, including imposing harsher sanctions or even considering limited military options. However, this option remains complex and would require a degree of U.S. adventure, given the significant regional risks that could arise from any military confrontation with Iran.
In conclusion, Trump administration’s decision to assign Witkoff, as part of a team, to handle the Iran dossier reflects not only the complexity and importance of this issue in U.S. foreign policy but also Washington’s desire to explore new pathways for dealing with this contentious matter. It would do so by testing the potential of diplomatic solutions alongside the continuation of "maximum pressure.”
