In the politics of the United States, an October Surprise is an unexpected event, contrived or unplanned, with the potential to influence the outcome of a November election. October Surprises date back to the 19th Century, but the term entered common parlance in 1980, when President Ronald Reagan, fearing that a last-minute deal to release American hostages held in Iran might earn incumbent Jimmy Carter enough votes to win re-election, allegedly made a secret deal with Iranian leaders to delay the release of the hostages until election day. Reagan won, and on the day of his inauguration—minutes after he concluded his 20-minute inaugural address—the Islamic Republic of Iran announced the release of the hostages. The alleged goal of the deal was stopping Carter from pulling an October Surprise. In short, Reagan beat Carter to the punch. Reagan’s frontman, William Casey, had mentioned the term “October Surprise” to the press more than once.
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This is a good theory, but I don't think future President Reagan had any ability to influence any foreign nation on anything. Recall that President Carter worked until the very last hour to free the hostages.
Reagan's VP was the former head of the CIA. The Reagan Bush team had plenty of power to negotiate with Iran behind Carter's back. Rosalyn Carter always thought the Reagan team had subverted her husband extra-legally.
It is hard to say. I think Jimmy's refusal to debate Reagan and then debating him at the last minute and then losing had more of an impact. There is also the contested Democratic Primary that hurt Jimmy in 1980 just like it hurt Bush Sr. in 1992. If there was at least a framework for a hostage release deal, but it was scuttled right before the election, it is quite possible Jimmy has his second term. That is because the media would have ran with the charge of election interference from the Reagan/Bush team.