Sidney Pen, also known as The Fat Man, is a minor antagonist in the videogame Mafia II and appears as the primary antagonist in the fifth chapter "The Buzzsaw". He was an associate of Don Alberto Clemente.
Sidney Pen, also known as The Fat Man, is a crooked businessman and an associate of Don Alberto Clemente in Empire Bay. The pair of them fell out in 1939 when Sidney opened up a distillery in Sand Island and refused to give Clemente a piece of the action. Clemente put out a hit on Sidney, but his men failed to complete the task and ended up being killed.
In 1945 Clemente soldato Henry Tomasino is hired to kill Pen, with associates Joe Barbaro and Vito Scaletta acting as backup. Henry briefs the pair on Pen, stating how he was underestimated in the past but assured they would get him. Henry rented an apartment across the road from Pen's distillery. When he arrived with his armed guards, they tried to hit him but he escaped inside, forcing the three to chase him on foot. After gunning down and killing masses of Pen's men, they finally corner him. Pen begs for his life, but this falls on deaf ears as Henry sticks a gun in his mouth and prepares to kill him. But Pen manages to shoot Henry in the leg with a concealed gun, an act with prompts Joe and Vito to riddle him with bullets, killing him.
- Sidney mentions that he has a wife, and uses this to try and plead for his life.
- Sidney is only referenced to by his alias "The Fatman" during dialogue in the game. His full name is given in the family album which is unlocked once completing Mafia II.