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An unexpected, dramatic last-minute event which potentially alters the outcome of an election. The term dates to the 1980 presidential campaign, in which Jimmy Carter planned, for October of that year, an operation to rescue American hostages held in Iran. Carter was lagging behind in polls and a successful rescue, an "October surprise," would likely have shifted the momentum to his side. The attempt failed, however, and Carter lost the election. Some have suggested that the Reagan campaign deliberately sabotaged the effort in order to bolster his candidacy.
Before Osama bin Laden released his newest tape, some people thought the Bush campaign would produce him as an October surprise.
by Sam Sundquist November 01, 2004
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Jun 21 Word of the Day
A person with an outwardly dominant, masculine, or aggressive personality, but who also enthusiastically takes on the submissive or "bottom" role in the bedroom.
"I'm tough, Mike! I never give an inch! I'm partial to taking a few though..."
"Ah, you're a real pipehitter."
by Skeletalchemy June 15, 2021
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When, in a last minute effort to become re-elected, a political figure happens upon a bit of "lucky coincidence."
News from October 31: We found Osama!

... although we really had his ass in a cell under the Pentagon the last three years.
by K Dawg Plus September 06, 2004
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An October Surprise can also mean a political challenger's orchestrated and delayed release of damaging information about an incumbent opponent just in time for an election.
Some political operatives had known about Mark Foley's pecadilloes for months in advance, but chose a timed release of the news as an October Surprise.
by NickB1967 November 08, 2006
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When doing a girl doggy style, just before you blow your load...You smash a pumpkin over her head! Similar to a donkey punch.
After the Halloween party, I grabbed the jack-o-latern and gave that girl an october surprise.
by jelly tug August 30, 2008
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Sex in a bed of leaves.
After the kids piled up the leaves, me and the wife had a little 'October Surprise'
by Bubbaice July 11, 2012
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6
1 Hilary's last effort
2 Hilary shows everyone her penis thus causing some male chauvenits to give her another look; a cock out

As Obama leads the polls going into super tuesday, Hillary knows that when october rolls around unsheathing her penis will be the only way to sway male voters in her direction.

Hilary has a 6in October Surprise
by tombo5 January 30, 2008
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