**Trump's public openness to engagement with Iranian officials centers on President Masoud Pezeshkian rather than Supreme Leader Mojtaba Khamenei.** Recent statements from the US president highlight three policy options toward Iran—military action, economic pressure, or a deal—while expressing conditional willingness for talks at the UN General Assembly. Iranian diplomats and advisers to Khamenei have consistently described any direct Trump-Khamenei meeting as unrealistic, emphasizing lower-level negotiations, asset releases, and confidence-building steps instead. A June 2026 memorandum of understanding between the presidents collapsed amid renewed hostilities and violations, leaving bilateral communication focused on mediators and working-level channels. No verified direct verbal or in-person contact between Trump and Khamenei has occurred, and structural barriers, including Khamenei's limited public role and Iranian rejection of high-level personal diplomacy, continue to shape low implied probabilities in related markets. Scheduled diplomatic windows such as the UNGA session remain the primary near-term catalysts.