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Have you guys ever heard of the S.S America? If not, don’t worry. To summarize, it was a cruise ship from long ago that had a rather long history. It went under many names, was owned by multiple companies, and was even used (To my knowledge) in one of the world wars to carry soldiers overseas to combat. However, it eventually fell into decay. A buyer/admirer of the ship did purchase it with plans to turn it into a hotel to preserve it’s legacy. But tragically, en route to the port, an accident forced the crew who were towing the ship to cut their cables, allowing it to drift endlessly on the open ocean. It eventually washed ashore on an island before slowly decaying away into nothing. The idea of a huge empty ship being set adrift with nary a soul inhabiting it is terrifying as it is tragic. Now why do I bring up the story of this great vessel? Well it inspired this theory/speculation that I have about Cloudsdale as well as the drawing itself.
Since magic had disappeared from Equestria, the pegasi who were inhabiting the city were forced to leave as they could no longer fly or walk on clouds. Because of this, Cloudsdale was set adrift in the sky. And with none of it’s inhabitants to maintain it, it slowly fell into decay, eventually becoming lost with time. Today in the modern days of Equestria, the city has become nothing more than a thing of legend. That is until a certain pair of pegasus sisters just so happen to discover it while trying to escape the tempest of a deadly thunderstorm.