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October Surprise is the allegation that representatives of the 1980 Ronald Reagan presidential campaign arranged the Iran-Contra deal well in advance of the 1980 election where Ronald Reagan defeated Jimmy Carter. October Surprise is also the title of a book on the subject by Gary Sick. This usage of the term describes a situation where a Presidential incumbent uses his office to do something very popular at the last minute before election day, to increase his chances of getting reelected. Thus the alleged conspiracy was precisely to prevent an "October Surprise" that would have aided Carter, the incumbent, effected by postponing the release of the hostages held by Iran until after the election.
The most public face of the story is simply that though in October of 1980 an agreement was reached, after long negotiations, to unfreeze Iran's monetary assets for the safe return of the hostages, yet, for some reason, the hostages were not released until January 20, 1981, the very day that Ronald Reagan was inaugurated as president.
Proponents of the theory, such as Barbara Honegger, a researcher and policy analyst with the 1980 Reagan/Bush campaign (interviewed in link), allege that William Casey and other representatives of the Reagan presidential campaign made a deal at two sets of meetings in July and August at the Ritz Hotel in Madrid with Iranians to delay the release of Americans held hostage in Iran until after the November 1980 presidential elections, so that Reagan's opponent, the incumbent President Jimmy Carter, whose team had been negotiating, wouldn't gain a popularity boost (an 'October Surprise') before election day. The allegations included a date-specific allegation that William Casey met with an Iranian cleric in Madrid, Spain, and much of the tardy investigations have centered on whether, at the weekend in question he was actually at Bohemian Grove retreat in California. Though William Casey was probably in London following the alleged meetings, critical pages of his daybook diary were unaccountably missing when the investigators came to look for them over a decade later.
Carter was at the time dealing with the Iran hostage crisis and the hostile regime of the Ayatollah Khomeini. Those who aver that a deal was made allege that certain Republicans with CIA connections, including George H. W. Bush, arranged to have the hostages held through October, until Reagan could defeat Carter in early November, and then be released. The hostages were in fact released on the very day of Reagan's inauguration, twenty minutes after his inaugural address. The timing of the release did not spark much press attention at the time.
Two months earlier, in a campaigning interview Ronald Reagan had said that he had a "secret plan" involving the hostages. "My ideas require quiet diplomacy," he had responded when pressed, "where you don't have to say what it is you're thinking of doing."
A 1981 Congressional probe into the Reagan campaign's theft of White House briefing books on the eve of a presidential debate disclosed that Reagan campaign manager William Casey (later appointed as Director of Central Intelligence in the Reagan administration) was receiving highly classified reports on closely held Carter administration intelligence on the Carter campaign and the Democratic president's efforts to liberate the hostages.
A Public Broadcasting System's 'Frontline' documentary in 1990 brought the story unavoidably to the surface in detail. In 1991, while playing golf with George Bush in Palm Springs, Ronald Reagan gave reporters a sound bite. In 1980, he had "tried some things the other way," that is, to free the hostages, he told them. When pressed he said that the details remained "classified."
Separate House and Senate investigations were further delayed until 1992. William Casey, the alleged go-between, was dead by then, and it seemed impossible to account for all his moves during the summer of 1980, when he is said to have conferred with agents representing the Ayatollah Khomeini's government.
If the allegations are true, some believe that dealing with a hostile foreign government to achieve the defeat of a domestic administration would have been an act of treason.
According to Sick's theory, Oliver North was the administration's scapegoat, taking responsibility in order to conceal the "treason" of Reagan and Bush. A PBS documentary, "The Secret Government," hosted by Bill Moyers, detailing the "off the shelf, self-financing, independent covert operations" entity mentioned by North, and tracing it to its cold war beginnings won an Emmy for best documentary film.
See also: George Bush family conspiracy theory, Iran-Contra, Iran hostage crisis