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Most likely first used in the early 1900s, either refers to a sarcastic remark about Toledo, Ohio or originated from a realistic remark of the Holy city of Toledo, Spain. It is now used as a phrase, by Americans, if something is unbelievable, disturbing, or blows their mind. See blow your mind
Woman- Did you read in the newspaper that a grandpa got run over by his own car by a homeless bum he paid to fix it, and then the bum took off with it?

Man- Holy Toledo?! That's like "Grandma Got Ran Over By a Reindeer" only a hundred times worse!
by DeJo August 02, 2005
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On May 25, 1085 Alfonso VI of Castile kicked the Moors out of Toledo, Spain; after which Toledo became one of the great centers of Christian culture. Hence the nickname "Holy Toledo". It has since evolved into an exclamation exhibiting surprise, probably due to original surprise that a Moor-encrusted place could become Holy.
Jimmy: Hey John! Did you know that Captain Kirk just beat Wolverine?
John: Holy Toledo! No Way!
by MidnightCricket May 01, 2009
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A phrase coined by gangsters and bootleggers in the 1920's. Due to Toledo's convenient location (Lake Erie Shore, ~halfway Chicago/Cleveland and ~a hour south of Detroit) it became the save haven for prohibition criminals after completing jobs in the larger cities previously mentions. A large portion of the crime in those cities was organized in Toledo. Toledo became known as the "Promised Land" to these mobsters, knowing they were in the clear once they made it back to Toledo. Hence the phrase Holy Toledo.
Holy Toledo did you see that!
by zzzzzzaaaaaccccchhhhhhh May 04, 2010
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A sexual act that involves the trinity orafices of a female's body (the mouth, the vagina, and the anus). Three men simultaneously penetrate the three orafices while holding hands and saying, "Oh God, Oh God" until they 'reach the promiseland'. It is named after Toledo because Toledo is the land god forgot.
Lauren was at Arnie's Bar&Grille when she was propositioned by three members of the boy band Booze Money to be the Mary Magdalen of their Holy Toledo. To which she responded, "I'd be down but I have lock jaw, a UTI, and I just ate some Tony Packo's."
by Clang May 01, 2006
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