How not to "convert" a pocket watch

There isn't necessarily anything wrong with it, it might have been made like that for someone like a pilot who would have his arms extended in front of him for hours on end and having the face rotated in that fashion would make it easier to read the time.

I doubt if that was ever a pocket watch because it's very slim and doesn't appear to have any mounting for a chain. That winder was a very neat retrofit if that device started life as a pocket watch.

Remember that before electronic devices for measuring the pulse (heart rate), nurses used to wear fob watches which to an observer was an upside down watch hanging from the lapel so there have been instances of non-standard mountings for specific people.