Donald Trump and Mojtaba Khamenei meet before Jan 1, 2027?

- [2026-02-28] US and Israel launched large-scale strikes on Iran, assassinating then-Supreme Leader Ali Khamenei; war has continued since. Trump's demand to be "involved" in choosing the next leader was rejected. https://www.cfr.org/global-conflict-tracker/conflict/confrontation-between-united-states-and-iran - [2026-03-08] Iran's Assembly of Experts named Mojtaba Khamenei (Ali's son) as the new Supreme Leader; Trump had criticized the choice beforehand, calling the son "a lightweight" and insisting "I have to be involved in the appointment." https://abcnews.com/International/mojtabakhamenei-becomeirans-supreme-leader/story?id=130781168 - [2026-06-04] Trump said he would meet the Iranian leader if a deal is reached to end the war: "If we make a deal, it's possible that I would meet," adding he expects Khamenei to be a "professional" despite the strikes killing his father. https://www.cnbc.com/2026/06/04/trump-iran-supreme-leader.html - [2026-06-05] A senior Khamenei military advisor, Mohsen Rezaei, shot down the possibility of a meeting between US President Donald Trump and Ayatollah Mojtaba Khamenei , while linking any deal to release of $24bn in frozen Iranian assets. https://www.cnn.com/2026/06/05/world/video/mohsen-rezaei-exclusive-trump-will-not-meet-supreme-leader-intl-dsk - [2026-06-18] Mojtaba Khamenei authorized direct talks with the U.S. in his first public response to the signing of the U.S.-Iran memorandum of understanding (MOU), but warned this did not signal agreement with Washington. https://www.axios.com/2026/06/18/iran-us-deal-supreme-leader-mojtaba-khamenei-talks - [2026-06-17] A memorandum to end the war was signed by the US and Iranian presidents (not the Supreme Leader), per Wikipedia's war timeline, lifting dual blockades, but tensions re-escalated and the ceasefire collapsed on 8 July after Iranian attacks on shipping in the Strait of Hormuz. https://en.wikipedia.org/wiki/2026_Iran_war - [2026-09-29] Araghchi (Iranian FM) met Qatari mediators in New York on a Hormuz reopening plan; a US official said there would be no deal unless Iran's nuclear program is addressed — talks remain indirect, with no Trump–Khamenei contact reported. https://www.aljazeera.com/news/2026/9/29/irans-araghchi-meets-qatari-mediators-as-us-insists-on-nuclear-talks - [2026-10-05/06] Trump stated that he remained "always open" to direct negotiations with Tehran, and Qatar confirmed that US-Iran discussions are occurring, with messages exchanged through Qatar and regional partners — i.e., indirect, intermediary-based contact only. https://en.wikipedia.org/wiki/2026_Iran_war - [2026-10-06] VP JD Vance said Iran would need to make a "meaningful" reduction in its uranium enrichment capacity to meet U.S. demands and end the seven-month war. https://www.cfr.org/global-conflict-tracker/conflict/confrontation-between-united-states-and-iran - [2026-10-08] Trump announced the United States would not pursue additional military action against Iran until after the U.S. midterm elections , while the Treasury simultaneously imposed new sanctions on Iran's shadow tanker fleet. https://www.cfr.org/global-conflict-tracker/conflict/confrontation-between-united-states-and-iran - [2026-10-08] Separately, the Pentagon reportedly ordered CENTCOM to prepare further strike options that could be launched before the midterms, and a White House official said "the Iranian regime is in a state of collapse," per The Atlantic/Washington Times. https://www.washingtontimes.com/news/2026/oct/8/trump-may-authorize-strikes-iran-midterms-report/ - [2026-10-09] IRGC claimed a strike on a tanker transiting the Strait of Hormuz, underscoring ongoing low-level hostilities even amid diplomatic contacts. https://www.cfr.org/global-conflict-tracker/conflict/confrontation-between-united-states-and-iran - [2026-10-08] Mojtaba Khamenei has not been seen in public since the war began and is reported to have been wounded (WIA) in the strikes; Iranian officials have cited security concerns against increasing his public appearances, making any in-person or even direct virtual/phone meeting logistically and politically fraught. https://en.wikipedia.org/wiki/2026_Iran_war BOTTOM LINE: As of October 2026 the US and Iran remain in a state of active, if intermittent, war with only indirect, Qatar-mediated communication; Trump has repeatedly floated openness to eventually meeting Mojtaba Khamenei "if a deal is reached," but Iranian officials (including a senior Khamenei adviser) have explicitly denied any such meeting is planned, and Khamenei himself remains unseen in public since being wounded, with no indication of a scheduled or imminent direct contact before year-end. NOT FOUND: No evidence of any direct phone call, video call, or in-person meeting having occurred between Trump and Mojtaba Khamenei; no official schedule or summit announcement involving the two leaders for the remainder of 2026.

- [2013-09-24] No sitting U.S. president has met in person with any top Iranian leader since the Shah's fall; even a mere handshake between Obama and President Rouhani at the UN in 2013 was aborted because Iran called it "too complicated." The last leader-level encounter was the first in-person interaction between the two nations' leaders since 1977, before the Shah fled Iran and the 444-day hostage crisis severed diplomatic ties . (world.time.com) - [2013-09-24] Even a scripted "encounter" (not a meeting) was explicitly rejected by Tehran: White House officials said they offered to have an "encounter" on the sidelines of the U.N. General Assembly, but the Iranians said it was "too complicated" at this point. This shows that even low-stakes, symbolic contact has historically failed to materialize. (npr.org) - [2025-02-07] Under the previous Supreme Leader (Ali Khamenei), direct talks were repeatedly rejected: Iranian Supreme Leader Ayatollah Ali Khamenei has dismissed the prospect of nuclear talks with the United States, insisting negotiations would not address Iran's problems... insisted it would "not be intelligent, wise, or honorable" to negotiate with Washington. (globalsecurity.org) - [2026-02-28] Ali Khamenei was killed in US-Israeli strikes, and a previous plan to assassinate Khamenei by Israel during the Twelve-Day War on 15 June 2025 was vetoed by Trump, according to unnamed US officials , indicating a long run-up of hostility before the base rate shifted toward his son. - [2026-03-08] Mojtaba Khamenei, previously a secretive, publicly unseen figure, was named new Supreme Leader; as reported, unlike his father, the 56-year-old has largely kept a low profile. He has never held government office, nor given public speeches or interviews, and only a limited number of photos and videos of him have ever been published. This makes any direct meeting (let alone a call) historically unprecedented for a figure who avoids public engagement. (yahoo.com) - [2026-06-03] Trump publicly floated the idea for the first time, telling the New York Post: "I'd like to meet him," ... "I would like to meet him and we probably will meet at some point, depending on how it all works out," but conditioned it on reaching a deal. (globalsecurity.org) - [2026-06-04] Trump reiterated conditionality: "If we make a deal, it's possible that I would meet," he said. "I'd be okay with that." No deal has since been confirmed as finalized. (cnbc.com) - [2026-06-04] Iran's government publicly downplayed the idea rather than endorsing it: Iranian Foreign Minister Abbas Araghchi dismissed President Donald Trump's remarks about meeting Mojtaba Khamenei, saying the issue should be viewed "realistically"... Araghchi said security agencies had advised against increasing Khamenei's public appearances because of security considerations. (iranintl.com) - [2026-06-05] A Khamenei military adviser was blunter still: Mohsen Rezaei, a military adviser to Khamenei, adamantly poured cold water on the idea of such a meeting. "This will not happen," Rezaei told CNN. "Right now we are in the first stage of negotiations and Mr. Trump has brought the negotiations to a standstill. " (thehill.com) - [2026-06-05] Analysts framed Trump's openness as consistent with a broader pattern rather than Iran-specific momentum: it is consistent with other instances where Trump has been willing to sit down with enemies or adversaries prior presidents would have avoided entirely — e.g., Kim Jong-un summits — but those took many months of advance staff-level work and still excluded the reclusive Iranian clergy's top office. (thehill.com) - [2026-10-08] As of the latest public update, U.S.-Iran contact remains indirect: talks restarted with the Islamic Republic through mediators at the United Nations General Assembly last month , with Trump confirming no strikes before the midterms but no reported direct Trump-Khamenei contact of any kind (call, video, or in-person). (townhall.com) - [2026-10-08] Trump's own framing remains focused on sanctions/deterrence rather than imminent summitry: he posted "IRAN WILL NOT HAVE A NUCLEAR WEAPON!" The president plainly declared his frequent message since the start of the conflict: "IRAN WILL NOT HAVE A NUCLEAR WEAPON!" — rhetoric that is not the tone of a leader on the verge of a historic sit-down. (townhall.com) BOTTOM LINE: The reference class (49 years of zero in-person or direct leader-to-leader U.S.–Iran contact, including a failed symbolic "encounter" attempt in 2013) and the specific post-war context (Iranian officials and Khamenei's own adviser publicly rejecting the idea, a reclusive new Supreme Leader who has never given an interview, and talks currently proceeding only through intermediaries) both argue for a very low base rate of such a meeting occurring within any ~6-month window, despite Trump's rhetorical openness. NOT FOUND: No evidence of any scheduled or confirmed Trump–Mojtaba Khamenei meeting, call, or video conference as of October 10, 2026; no betting-market or pollster-specific probability estimates for this exact event were located (other than the Kalshi contract itself, which was excluded per instructions).

YES means: Donald Trump and Mojtaba Khamenei have a documented direct interaction — in person, by video, or by phone — before January 1, 2027, satisfying the Kalshi definition of a "meeting." - [2026-06-04] Trump has publicly and repeatedly committed to the idea in his own words, not just as a hypothetical aside: "If we make a deal, it's possible that I would meet," he said. "I'd be okay with that." This is a standing, self-stated conditional offer that remains open as of the most recent reporting, giving Trump a ready-made public rationale to agree to contact the moment a deal materializes. (cnbc.com) - [2026-06-03] Trump's commitment predates and is more specific than mere openness — he told the New York Post "I'd like to meet him," ... "I'd love to meet everybody. I would like to meet him, and we probably will meet at some point, depending on how it all works out." (washingtontimes.com) - [2026-05-24] Crucially, Mojtaba Khamenei is already reported as a direct participant in deal-making at the top level, not a bystander: a senior U.S. official said "Our understanding is that the Supreme Leader, Mojtaba Khamenei, has endorsed the broad template of the deal." This shows the infrastructure for leader-level sign-off already exists, shortening the remaining distance to direct personal contact once terms are finalized. (axios.com) - [2026-10-09] The diplomatic channel remains live and is described by Trump himself as making progress: Trump said Witkoff was making progress in negotiations with Iran but suggested that reaching a deal was not his preferred outcome. Trump also predicted the war "will end 'very soon,'" keeping a near-term endgame — and thus a meeting trigger — plausible within the market window. - [2026-10-09] Iran's own foreign minister signaled momentum toward a formal response: Iranian Foreign Minister Abbas Araqchi said Tehran will answer a US proposal within days while indirect talks continue through mediators... He said Iran had presented a seven-day plan and is now reviewing American views. A formal response is expected shortly, with messages still moving through intermediaries between the two sides this week. A concluded deal on this fast a timetable would activate Trump's own "if we make a deal" meeting pledge well before year-end. (israelhayom.com) - [2026-10-08] Trump has created a concrete deconfliction window that favors diplomacy over escalation in the near term: he said the "We will not be attacking Iran at any time prior to the Midterm Elections to be held in the United States on November 3rd" — a declared pause in hostilities that gives negotiators roughly a month of reduced military risk to convert the Witkoff/Kushner channel into a finalized deal. - [2026] Trump's broader diplomatic pattern — documented by analysts — shows a track record of being willing to personally meet reviled or reclusive adversarial leaders once talks reach a certain stage, as with his North Korea summitry with Kim Jong-un, framed explicitly as a precedent for the Khamenei case: "it is consistent with other instances where Trump has been willing to sit down with enemies or adversaries prior presidents would have avoided entirely — or at least treated with extreme wariness." (thehill.com) - [2026-04-01] Even amid denials of "negotiations," Iran's own foreign minister has already confirmed an operating direct-contact channel with Trump's inner circle: Iran's top diplomat Araghchi has confirmed direct contact with United States President Donald Trump's top envoy Steve Witkoff amid the ongoing war... "I receive messages from Witkoff directly, as before, and this does not mean that we are in negotiations," showing that direct (if sub-leader) US-Iran contact is already normalized, lowering the remaining procedural barrier to a leader-level call once political will aligns. (aljazeera.com) - [2026-10-08] A U.S. official's framing that "an agreement was 'really' not what he wanted but that Iran was willing to offer concessions to bring the conflict to an end" indicates Tehran is the more eager party for a deal — raising the odds Iran would accede to a symbolic leader contact (e.g., a call) as a face-saving/concession gesture to lock in sanctions or blockade relief from Washington before the window closes. BOTTOM LINE: The strongest path to YES is a rapid sequence — an active, Trump-touted Witkoff/Qatar-mediated negotiation reaching a signed deal within the Nov-3-midterm-to-Jan-1 window — after which Trump's own repeated, specific, and still-standing pledge to meet "if we make a deal" would almost certainly be invoked, especially given his track record of personally rewarding deal completion with leader-level contact (Kim Jong-un precedent) and reports that Khamenei has already engaged with the deal's substance via intermediaries. NOT FOUND: No evidence of a scheduled call/meeting, no confirmed finalized deal text, and no statement from Khamenei's camp since the June 2026 rejections softening their position on a leader-to-leader meeting specifically (as opposed to continued intermediary talks).

YES means: Donald Trump and Mojtaba Khamenei have direct real-time contact (in person, video, or phone call) at any point before January 1, 2027. - [2026-08-18] Trump stated flatly "There are no talks or conversations going on, or scheduled, with the Islamic Republic of Iran," even as his own envoy Jared Kushner claimed backchannel conversations were "more robust than it's maybe ever been" — showing the U.S. side itself describes contact as indirect at best, not leader-to-leader. https://www.usnews.com/news/world/articles/2026-08-18/trump-says-no-talks-are-taking-place-with-iran-and-none-are-scheduled - [2026-09-26] Iran's President Pezeshkian, not Khamenei, is the one fielding interviews (CBS) and conducting diplomacy; he described his own meeting with Khamenei lasting "over seven hours," underscoring that even Iran's head of government only sees Khamenei rarely and that Khamenei himself has "no specific ongoing health issues" despite not being seen or heard in public since the war with the U.S. and Israel began in February , per PBS/AP. https://www.pbs.org/newshour/world/trump-rejects-irans-proposal-to-reopen-the-strait-of-hormuz-and-other-middle-east-news - [2026-09-26] Trump publicly rejected Iran's latest proposal (reopening Hormuz in 7 days for sanctions relief and a ceasefire including Lebanon), calling it unacceptable because Iran was "losing so badly" -style rhetoric — a posture of continued pressure, not summit diplomacy. https://www.pbs.org/newshour/world/trump-rejects-irans-proposal-to-reopen-the-strait-of-hormuz-and-other-middle-east-news - [2026-10-08] Trump said bluntly "I think the deal isn't really something that I want to do, but they're willing to offer us anything to stop" — explicitly stating he no longer wants a deal, which under his own June 2026 framing ("if we make a deal, it's possible that I would meet") removes the precondition he himself set for any meeting. https://cnbc.com/2026/10/08/us-iran-war-trump-hormuz.html - [2026-10-09] Trump announced on Truth Social: "we are having productive discussions with the Islamic Republic of Iran," ... "We will not be attacking Iran at any time prior to the midterm elections to be held in the United States on November 3rd." This freezes major escalation but also signals no leader-level summit is imminent — only continued indirect "discussions." https://www.aljazeera.com/news/2026/10/9/trump-says-us-will-not-strike-iran-before-midterm-elections - [2026-10-09] Al Jazeera analysis notes Trump has a track record of reversing stated restraint — he struck Iran in February despite saying the day before "he had not made any decision," and struck in the 2025 12-day war despite promising a "two-week" decision window — meaning any current lull is fragile and could flip to renewed war rather than diplomacy. https://www.aljazeera.com/news/2026/10/9/is-trump-signalling-a-return-to-war-with-iran-after-the-midterms - [2026-10-09] The same analysis notes that resuming war after the midterms "may have less of a negative impact on Trump," since he is not eligible to run for another term as US president anyway — suggesting the political incentive structure favors renewed strikes over rapprochement once midterms pass, pushing any potential deal/meeting window further out or off the table entirely before 2027. - [2026-10-09] IRGC Navy attacks on shipping (LPG carrier near Hormuz) and Saudi airport strikes blamed on Iran-aligned actors continued into this week, confirming active hostilities persist in parallel with "productive discussions," per ABC News live updates. https://abcnews.com/International/live-updates/iran-live-updates-trump-us-attack-iran-ahead/?id=137063637 - [2026-07-20] Mojtaba Khamenei's own location was reportedly unclear with speculation he "may have fled Iran" to Russia for safety, and he has been almost entirely absent from public view, and the extent of his behind-the-scenes power remains deeply uncertain. He did not even make a public appearance during the recent days-long funeral ceremony for his father. This underlines the logistical/security barrier to any direct or video contact with a foreign head of state. https://www.washingtontimes.com/news/2026/jul/20/mojtaba-khamenei-still-iran-supreme-leaders-whereabouts-unclear/ - [2026-07-22] Even Iran's own foreign minister has never personally met Khamenei, per a National News report headlined on his inaccessibility — reinforcing that Khamenei's isolation predates and is independent of any U.S. diplomatic posture, making a Trump meeting exceptionally unlikely on logistics alone. https://www.thenationalnews.com/news/mena/2026/03/11/where-is-mojtaba-khamenei-iranian-officials-say-new-leader-is-lightly-injured/ BOTTOM LINE: Contact remains exclusively indirect (Qatar/mediator channels), Trump has pulled back from his own "if we make a deal" precondition by saying he no longer wants a deal, active hostilities (Hormuz attacks) continue alongside diplomacy, and Khamenei himself remains reclusive even to Iranian officials — all pointing to a very low likelihood of any direct Trump–Khamenei contact materializing before January 1, 2027. NOT FOUND: No scheduled summit, call, or video conference between Trump and Mojtaba Khamenei; no confirmed post-midterms (after Nov 3) diplomatic calendar; no statement from Khamenei's office addressing Trump's meeting overtures since the June 2026 rejections.