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Holy Toledo! is an expression that's probably slipped out of usage now except among comic book characters and government officials with a taste for mild expletives. The phrase has a curious etymology. In medieval and Renaissance Europe, two cities were considered great centers of mystical and occult learning, Toledo being one. Its high-vibrational, otherworldly nature can be seen in the paintings of El Greco, who frequently chose the city as a subject. Depicted in his characteristically elongated style, Toledo seems to be soaring upward, aspiring to something greater than the daily affairs of mankind: buying and selling, eating and drinking, working and sleeping.
http://www.worldandi.com/specialreport/2003/February/Sa22908.htm
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