An extended period of relative calm in the ongoing war between the United States and Iran was shattered in early September with a barrage of laser-guided munitions and ballistic missiles between warring parties. The chronology of escalation has naturally been disputed, with each side declaring that its own strikes were “retaliation” against the actions of its adversary. By the time that statements were released on Wednesday, September 9, five Iranian oil tankers had been sunk and as many as ten U.S. ships had been hit in and around the Strait of Hormuz. While Iran has blamed the U.S. for initiating this most recent round of violence, government spokesmen have also promised to escalate sharply, announcing an enlarged “exclusion zone” to further restrict shipping and promising to hit 20 enemy targets for every 2 or 3 Iranian targets hit. The escalation debate must also acknowledge the recent actions of the Ansar Allah “Houthis” in Yemen, a critical Iranian ally that simultaneously overran Saudi-allied forces to seize control of Yemen’s Red Sea coast and destroyed Saudi Arabia’s pivotal east-west pipeline just before the escalation in the Strait of Hormuz. As a consequence of these dual threats to oil traffic in the Red Sea and Persian Gulf, global oil prices have predictably skyrocketed, with Brent crude futures surging past $100 a barrel for the first time since a brief blip in July. Echoing prior warnings from hawkish Iran observers in the United States, analysts have increasingly begun to describe this violence as Iran’s “October Surprise,” a calculated attempt to sway U.S. public opinion ahead of the November midterm elections.

The phrase “October Surprise” is now ubiquitous in American politics, used to describe a variety of high-profile events that could decisively influence the outcome of upcoming November elections. While the phrase is sometimes used for natural disasters and other spontaneous events, “October Surprise” more typically refers to a scandal or crisis deliberately exposed or instigated by an opponent with the express goal of gaining an electoral advantage. The first person to use the phrase was Bill Casey, Ronald Reagan’s campaign manager, who warned in July 1980 that President Jimmy Carter was likely to exploit the office of the presidency to manufacture “good news” to aid his campaign against Reagan. While Casey’s initial warning did not mention Iran, subsequent Republican warnings of an impending “October Surprise” focused heavily on the possibility that Carter might negotiate a last-minute deal with Iran to release the remaining 52 American hostages held in the country since November 1979. Iran’s motive for reaching such a deal with “the Great Satan” was obvious, as Casey frequently told the press: they understandably feared the replacement of the hapless and ineffective Carter with a resolute and hawkish Reagan, who would not hesitate to bomb the country into submission.

The great irony of the original “October Surprise” is that it likely did take place, just in the precise opposite manner that Casey predicted. Rather than Carter striking a deal with Iran to release the hostages just prior to the November 1980 election, the Reagan campaign appears to have secretly colluded with Iran to prevent the release of the hostages until after the election. Even Iran hawks in the U.S. now agree that the Iranian government held the hostages for so long in order to punish President Carter with maximum political humiliation. The timeline – the hostages were finally released minutes after President Reagan’s inauguration – makes this point almost impossible to dispute. Whether or not the Reagan campaign actively encouraged this Iranian decision remains in dispute. Gary Sick, Carter’s Iran expert on the National Security Council, publicly alleged such interference in an article published in the New York Times in April 1991, claiming that Reagan promised the Iranians secret arms deliveries from Israel in exchange for their cooperation. These allegations were significantly more believable in the aftermath of the Iran-Contral Affair, in which the same individuals on both sides negotiated a similar deal, with Israel serving as the intermediary arms supplier. While the bipartisan House October Surprise Task Force found “no credible evidence” to support Sick’s allegations, recent scholarship has established “a solid evidentiary basis for the October Surprise theory to be considered an established historical fact.”

Could the November 2026 midterm elections see Iran spearheading another “October Surprise,” this team working to undermine Republican rather than Democratic electoral ambitions? The dynamics of such an “October Surprise” would work much differently in 2026 than they did in 1980. There are no serious allegations of secret Democratic collusion with Iran in the current conflict, so this would be a crisis manufactured almost entirely externally rather than a partisan political maneuver. Yet, there is no question that Iran has compelling interests in working for the electoral defeat of the Republican Party. While the Iranian drive to humiliate Jimmy Carter is often linked to an essentially psychological desire for revenge, the current incentive to aid Democratic candidates would be much more clearly strategic in material terms. This is a spectacularly unpopular war, driven by the recklessness of the Trump Administration, which has been left unchecked by the Republican-controlled Congress. Would such an “October Surprise” work? The oil price gambit remains precarious. While there is no question that higher prices at the pump will aid Democratic electoral prospects, the Trump Administration will continue to pull all available levers to keep oil prices in check before the war. Similarly, the Democratic Party is not fully unified in opposition to the war, and it is not at all clear that a Democratic-controlled Congress would force the administration to end it. In the absence of alternative paths to extricate their country from the current war against a stubborn U.S. administration, however, it should surprise no one to see the Iranians start to put their thumbs on the scale in any way that they can.