There are expressions that for whatever reason, remain in the language for ever and ever, and we all use them without really knowing where they come from. Although, in the case of the “Toledo night” “noche Toledana” the matter of the location seems quite clear.
If you are Spanish, you have probably said those two words after some horrible and endless night, maybe because you had a hyperactive mosquito in the room, because a tooth hurts you or because you got a bad drink on your last orders. In other words, we already have another piece of information: the Toledo night is not a good thing. Let’s keep going!
There is a tower in Toledo called the Tower of San Cristóbal, and that’s what remains of an old Mudejar church dedicated to the Saint who was asked for help against plagues. Very close to it, around the year 800, they say it's where the most brutal and savage episode in those times took place.
According to the most devious version of the story, the city was ruled by a certain man called Yusuf, a despotic and evil fellow who took advantage of his power, and the people of the town ended up revolting against him and killing him. So the supreme head of al-Andalus, Caliph Al-Hakem, decided to send a new governor, and, would you believe, it was the father of the deceased who requested the honour.
His name was Amrus, and he promised to be fair and equitable to compensate the city for the outrages of his son. So he put himself in command of that mixture of races and faiths that was then Toledo and he governed it with prudence and honesty for a while. Long enough so the nobles who had led the revolt against his son could breathe a sigh of relief and feel safe. But, as you can imagine, they weren’t.
One day, Amrus announced the celebration of a splendid banquet to honour the Caliph’s son passing through the city. And of course, he invited all the members of the Toledo Royalty, who prepared themselves with their best clothes while the host’s guard sharpened their weapons.
Night fell, and between torches, hundreds of nobles were arriving, to the place of the party. One by one, the soldiers led them to a secluded area where their heads were sliced, and their remains were thrown into a ditch in absolute silence. After beheading the last of the guests, and with the ditch flooded with blood and corpses, Amrus cleared his throat and putting on his best face he declared that his son could rest in peace because revenge had been taken.
And due to this episode of history is why the Spanish expression, “Noche Toledana” is used when someone has had a bad night.