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!
Man- Holy Toledo?! That's like "Grandma Got Ran Over By a Reindeer" only a hundred times worse!
by DeJo August 2, 2005
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.
by MidnightCricket May 1, 2009
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.
by zzzzzzaaaaaccccchhhhhhh May 5, 2010
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 1, 2006
A divine group of three terms, all based around the city of Toledo, Ohio. This location was chosed due to the popularity of other Ohio-based terms Cleveland Steamer and Cincinatti Bowtie. The Trinity is comprised of:
The Toledo Mosquito
The Toledo Burrito
The Toledo Funguito
The Toledo Mosquito
The Toledo Burrito
The Toledo Funguito
Jim successfully made a 4,500 mile pilgrimage to Ohio in order to be in the city of his religion. He spent 29 days worshipping the town of Toledo and The Holy Toledo Trinity. He wept when he saw a live performance of the Toledo Burrito.
by The Earl of Teabag August 29, 2006