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Sidney Pen is a minor character in 2K Czech's 2010 sandbox game Mafia II. He appeared frequently in pre-release trailers and hype-building events, but is only seen once during the game. He appears in Chapter 5: The Buzzsaw. Sidney Pen is well known in the criminal underworld by the alias of 'The Fat Man', and is an ex-associate of Alberto Clemente. Sidney Pen was a bootlegger, and eventually attempted to leave Clemente's line of work, opening a distillery in Sand Island. He opened his distillery in 1938, and cut Clemente out of his new life, forgetting he ever existed. 
 
Clemente didn't forget though, sending Henry Tomasino to kill Sidney.  
 
Henry Tomasino recruits the help of Joe Barbaro, who vouches for Vito Scaletta to come along and aid them, seeing as he has had World War II experience. The three men make use of an apartment situated across the road from the distillery, as well as a German MG42 smuggled back into the United States. When Pen's convoy of vehicles arrive carrying him and his bodyguards, the three men strike, destroying all of the cars and wiping out the majority of Sidney Pen's aides. However, Pen himself escapes the ambush unscathed, running into the distillery to hide. Tomasino, Scaletta and Barbaro follow into the distillery, which is set ablaze by a Molotov Cocktail. After reaching Pen, he cowers in a corner, pleading for his life. Tomasino prepares to execute The Fat Man, but hesitates. Seizing an opportunity, Pen unholsters his .38 Snubnosed, and shoots Henry in the leg. He then tries to get up, and is cut down by Joe Barbaro and Vito Scaletta, armed with an M1928 Thompson and Colt M1911 respectively.  
 

Trivia

  • The Fat Man claims to have a family, as when Henry Tomasino puts the barrel of his gun into Sidney's mouth he screams out "Please, I have a wife!"
  • His real name is not revealed during the course of the game, and he is referred only to as either 'The Fat Man', or 'Fat Bastard'.
  • Sidney Pen appears to be well-off, as he travels in a Lassiter Series 75 Hollywood, which is a limousine.
  • The street on which Sidney Pen's distillery is located is called 'Misery Lane'.
  • Sidney Pen's voice was provided by John Capodice.

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