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Uncle Pennybags

Rich Uncle Pennybags is the rotund old man in a top hat who serves as the mascot of the game Monopoly. He also appears in the related games Advance to Boardwalk, Free Parking and Monopoly Junior. Despite the outcry from dedicated fans of the game, Rich Uncle Pennybags was rechristened Mr. Monopoly in a Hasbro marketing effort in July 2000.
The character first appeared on Chance and Community Chest cards in Monopoly in 1936. The artist who designed the character to appear across several of the cards has remained a mystery. According to The Game Makers, a book published in 2004 by Philip Orbanes, it is believed that the character is based on either the calling cards of Albert Richardson (Parker Brothers' first traveling salesman) or the character of "Little Esky" from Esquire magazine, or a combination of the two. The unnamed character made his first appearance outside of Monopoly within the Parker Brothers' game Dig, released before the U.S. entered W.W. II. The character did not receive a name until 1946, when the game Rich Uncle was published by Parker Brothers. His likeness appeared on that game's box lid, game instructions and currency.
In 1988, Philip Orbanes published the first edition of his book The Monopoly Companion. In the book, all of the characters that appear on the Monopoly board, or within the decks of cards, received a name. Uncle Pennybags full name was given as Milburn Pennybags, the character "In Jail" is named "Jake the Jailbird" and the police officer in the opposite corner to the jail is named "Officer Edgar Mallory."

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