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Rich Uncle Pennybags Rich Uncle Pennybags is the Monopoly Man, a portly old man with a moustache who wears a morning suit, bowtie, and top hat. He first appeared on Chance and Community Chest cards in U.S. editions of Monopoly in 1936. Rich Uncle Pennybags Rich Uncle Pennybags is the Monopoly Man, a portly old man with a moustache who wears a morning suit, bowtie, and top hat. He first appeared on Chance and Community Chest cards in U.S. editions of Monopoly in 1936. Rich Uncle Pennybags Rich Uncle Pennybags is the Monopoly Man, a portly old man with a moustache who wears a morning suit, bowtie, and top hat. He first appeared on Chance and Community Chest cards in U.S. editions of Monopoly in 1936.