Rich Uncle Pennybags

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Milburn Pennybags appears on this Christmas card sent to select business associates, December 1968

“Oh sure, Milli was a regular weekend guest at the house. He would always eat all the maraschino cherries but um...I never minded.”

~ Frank Sinatra

Milburn "Rich Uncle" Pennybags (also known as Mr. Monopoly or The Chinchilla Don) is a high-powered real estate financier and leader of the Monopliano crime family. First emerging onto the scene in 1936, Pennybags quickly gained mass notoriety for his flashy style and expensive tastes, as well as his allegedly[1][2] ruthless treatment of those who dare defy him.

Early Years

Milburn Pennybags was born Amil Penbaglio to Furio and Silva Penbaglio in 1918. As Italian immigrants, neither Furio nor Silva spoke English. In addition (and despite their Sicilian origins), neither knew anything about cooking, truck driving, dry cleaning, or trapeze artistry. As such, Furio worked odd jobs, and Silva was, out of necessity, a rodeo clown. Amil, an only child, exhibited an early interest in calligraphy. Later in life, Milburn commented "I learned two very important lessons as a young man. The first was that you can go farther in this world with a kind word and a gun than you can with just a kind word. The other was calligraphy." As an adolescent, Amil befriended cousins Harold and Carmine Risko, a pair of allegedly[3] low-level muscle men for the Monoplianos. The boys became a tactical team for the family, providing their morally questionable services with zero regard for the law or human decency.

In 1948 Amil legally changed his name to Milburn Penbaglio to avoid draft into Battleship War II. The name "Pennybags" would come later in his young adulthood, a reference to his aptitude for black market dealings (in this early case, the trade of heroin distribution). According to Luigi "Buckaroo" Buccazio, "He got that name because the kid was so good. If you was good, back then it was common for people to say 'wow, you must be good, they're comin' back for dime bags!' Well with Milli, he had 'em comin' back for pennybags."

In his early adult years, Milburn Pennybags showed an aptitude for earning that far outshone his young peers. With a growing network of dealings in numerous fields and markets (including a very lucrative relationship with the Hasborough County Housing Commission), Pennybags moved his way up the chain of command rapidly, much to the dismay of higher-ups in the family. However, Pennybags' savage handling of opposition was alive and well, allegedly[4] leading to the untimely deaths of several family captains, business associates and similarly opposing individuals. These incidents of violence would aptly foreshadow the occurrence on St. Yahtzee Day a few years later.

Candilano Estate Development

Main article: Candy Land

After a series of internal shake-ups within the Monopliano family, Pennybags found himself a high-ranking capo, controlling real estate ventures for most of the eastern seaboard. His most major accomplishment, however, came in the development of the boarder region between Milton-Bradley counties in the state of Nevada. This prime lot land would be completely rendered from the ground up by Pennybags' Candilano Estate Development group. The ensuing land would become one of the fictional world's greatest gambling enterprises: Candy Land.

Consisting of a number of themed hotels, restaurants, entertainment venues, and more neon than Tokyo, Candy Land quickly gained a reputation for its loose morals and 24-hour lobster buffets. World class gambling establishments such as the Molasses Swamp Towers and the Gumdrop Pass Resort and Spa further fortified the money-making enterprise that Candy Land would become and remain. It also solidified Milburn Pennybags as a captain of industry and considerable force to be reckoned with in the world of high finance.

Rise to Ultimate Power & The St. Yahtzee Day Massacre

With countless fingers in an astronomical number of delicious pies, it was all-but-inevitable that Pennybags would become acting boss of the Monopliano family. In the years after the development of Candy Land, Milburn would gain control of several highly lucrative operations, including Connect 4 Imports and Freight, The Stratigo Investment Consortium, and a number of Checkers fast food restaurants. At this point in time, his own estate contained four houses (and two hotels). This was unheard of for an underboss in 1982.

Little stood in the way of Pennybags' seizure of ultimate control, but there were still certain considerable elements that would need to be altered in order to make the transition to active Don. Chiefly, the elimination of opposition leaders, this time within the lower ranks of the family. This task would be executed in a most overt and gruesome fashion on St. Yahtzee Day.

BALTIC AVE. -- A bloodbath was discovered today in an abandoned warehouse along the Ouija Boardwalk stretch of the east bay. A number of the deceased have been identified as ranking members of the Monopliano crime syndicate. Among the dead were the following family associates: Jeffrey "The Car" Carbinaro, Scott "Scottie Dog" Marisi, Harry "Thimble" Timblino, Joseph "Guy on a Horse" Guyonahorsi, Joseph "Lil' Top Hat" Lito, Lester "The Boot" Centafanti, and Robert "Battleship" Baccaliani. Each man was bound and shot execution style, with blue fifty-dollar bills placed over their eyes. As is customary in gangland slayings, each man died with his driver by his side.[5]

View from the Top

Once seizing complete control, the world became Milburn's oyster. He seized a near-complete control of the drug trade, numerous prostitution rings, and continued the expansion of his fast food empire. He taxed DVD bootleggers and dog groomers. Your mother and father? In his pocket. Guaranteed. He owns your ass, pink boy.

States Evidence Exhibit C, Pennybags vs. The State of New York 1988 (charges dropped)

In order to maintain an air of legitimacy to his business practices, Pennybags gives to many charities regularly. The Cranium Fund, Feed the Hungry Hungry (a charity benefiting hippopotamus reserves), and the Crocodile Dentist Collective are often recipients of very generous donations from Pennybags. He is also known to have several ranking government ties, and is famous for his "Get out of jail free" cards. This, and also an extensive history in the field of loan sharking, earned Milburn the nickname "Rich Uncle." This was shortened from the original moniker "Rich Uncle who will break both of your kneecaps if you don't pay on time." The former is said to have a better ring to it.

Rich Uncle Pennybags does very little to hide his wealth. He is often seen out and about in expensive furs, sparkling jewelry and the finest designer bow ties (of which he favors Gucci). Never alone in his escapades, Pennybags generally keeps a gaggle of women on his arms, often numbering between four and seven. It is rumored that he has a fetish for Bangladeshi women and traditional silks of that region.

As a public figure, Pennybags has been spotted hobnobbing with many celebrities, including Prince, Mike Tyson and Noam Chomsky. A relationship with socialite Kim Kardashian has been rumored, but both claim to be nothing more than "good friends" and "occasional fuck buddies."

Future Endeavors

Pennybags has been quoted as taking a keen interest in the evolving geopolitical climate of the planet, and the galaxy at large. In early 2002, Rich Uncle made claims of a partnership between himself and maverick astronaut Richard Branson. To quote Pennybags directly: "You're damn right I want to go to outer space. There's money in outer space. I bet there's gold on Saturn...Saddle me up bitches, I'm gunna be president of the moon!"

In addition to his aspirations of manned space exploration, Pennybags is particularly interested in terrestrial enrichment projects in South America. Spearheading a multi-corporation effort, The Operation Initiative has taken charge in ridding the world of what Milburn refers to as "those land-consuming eyesores people call rain forests." Through these recent actions, almost 30% of the regions remaining forested areas have been cleared, paving the way for new and exciting retail ventures. "We want to give everyone on the planet an opportunity to buy things from me," Rich Uncle claims. "How are they going to do that with a bunch of damn trees and bushes in the way?!"

References and Annotations

  1. Canemaker, Candice. Pennybags sought in connection to Scrabbili Brothers Bakery fire 18 August 1976
  2. Bucco, Arturo. No "Sorry!'s" in Pennybag's Game of Life 30 June 1980
  3. Jenga, Mario. Risko boys evade assault, murder charges. 2 April 1965
  4. Brothers, Parker. "Pursuit of Pennybags seems trivial, says police commissioner. 6 June 1967
  5. Mon-Kees, Barrelo. Yahtzee Day Massacre boggles the minds of investigators. 8 February 1983

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