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Dec 20 - A shiny Uncle Pennybags! So maybe they are just giving shiny repeats of the most classic characters :D

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Apparently he won second prize for something (it’s on his sash). I think I know what for, but I want to hear your guesses! :D

Was it the beauty contest?

^ Well, there is a Community Chest card that reads "You have won second prize in a beauty contest".

Was he runner up in the TOUK Boopathon!?

Yes! The Beauty Contest! Although… I think Nelly’s answer also works :D