One of the few cities ever to be built on a whim. The tall tale goes something like this. Peter the Great wanted a city. He was currently at war against the Swedes and wanted a stronghold in the north. He got a map, pointed to a spot on it, and said "I want my city to be built here". This is the same man that trained two polar bears to serve vodka at court. Surely a man to be reckoned with.

In any case the city could not have been built in a worse area. Plagued by disease from the swamps and consistent flooding from the river Neva, it rather reminds me of Monty Python and the Holy Grail (the castle sinking into the swamp regularly). In Russia it was the first truly planned city, complete with a gridded streetplan, and modern sewer system. It completely weirded out the poor serfs who were forced to live there.

The movement of the whole Russian state to this city also alienated the Russian Orthodox church, ending what they had lovingly called the Third Rome (and in their eyes final) of Moscow. This was the beginning of the association of St. Petersburg with the apocalypse. It also didn't help that Peter the Great abolished the Patriarchy, removed the church from any real political power, made a mockery of them consistently in court and removed most of the most stringent cultural customs forcing women to live in a completely different part of the house and for forcing the nobility to cut off their beards.

Literature has not helped as well. Pushkin's poem "The Bronze Horseman" turns Peter the Great into a demiurge, the antichrist, and one of the four horsemen all at once with St. Petersburg as the focal point of the beginning of the end.