The term “October Surprise” originated against the backdrop of President Jimmy Carter’s 1980 reelection campaign. The Iranian hostage crisis overshadowed the last year of Carter’s presidency. William Casey, Ronald Reagan’s campaign manager, coined the term to describe the possibility that a last-minute hostage release might give his campaign a shot of adrenaline to enable him to win a second term. It took a conspiratorial turn when Gary Sick, a Carter national security aide, suggested that Reagan’s team had conspired with Iranian revolutionaries to delay the hostage release. The theory was later disproved.
Still, campaigns obsess about a last-minute surprise.
Iranian officials are sophisticated students of American politics; many studied in the U.S.
On Oct. 30, 1992, just four days before elections, the Justice Department indicted former Secretary of Defense Caspar Weinberger on a charge relating to the Iran-Contra Affair and linking President George H.W. Bush to an alleged cover-up. The timing derailed Bush’s efforts to shape the narrative in the final week before the elections and contributed to his defeat. Five days before the 2000 election, word leaked that Texas Governor George W. Bush had had a driving under the influence arrest in Maine nearly a quarter-century before. Bush ultimately won the election, but it was by many measures the closest in American history.
In 2016, a different surprise targeted each major presidential candidate. First, a video leaked showing Republican nominee Donald Trump talking about women in extremely crude terms. Just a few weeks later, however, FBI Director James Comey sent a letter announcing an investigation into Democratic nominee Hillary Clinton’s use of a private email server for official government business.
There will be no presidential election in 2026, but Trump’s diplomacy with Iran and his Memorandum of Understanding could readily set up an October surprise to derail Republican hopes in the midterm elections.
With inflation surging and against pressure from many within his own camp, Trump signed onto the Memorandum of Understanding with Iran. Trump depicts the deal as a victory for the United States, even as Iranian officials comment that they got far more from the president than they had ever imagined. As Iranian Parliamentary Speaker and chief negotiator Mohammad Bagher-Ghalibaf said on June 17, “Everything we sought to achieve through military action, we obtained several times over through negotiation; it was not even comparable.”
Trump has essentially empowered the Islamic Revolutionary Guard Corps to be a kingmaker on Nov. 3, 2026.
The interim deal will initially last only 60 days, although past practice suggests Washington and Tehran will likely extend it several times as negotiations are slow and Iran’s strategy is to run down the clock. In practice, this means that Washington and Tehran will still be operating under an interim agreement in the weeks and days before the 2026 midterms.
Iranian officials are sophisticated students of American politics; many studied in the U.S., and they understand better than American diplomats how to use time as a weapon. Vice President JD Vance, whose nativism makes him the 21st century’s Charles Lindbergh, may want to foist blame on Israel for a bad deal not holding, but Trump has essentially empowered the Islamic Revolutionary Guard Corps to be a kingmaker on Nov. 3, 2026.
Trump may declare the Iran deal a diplomatic triumph, but the Iranians can change that narrative by closing the Strait of Hormuz in October. There is nothing more the Iranian regime would savor than embarrassing Trump. That the U.S. president has essentially provided them a noose of his own making is an irony the Islamic Republic will both savor and enjoy.
Published originally on June 22, 2026.
