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Simon is responsible for checking the first shipment of alcohol Rothstein buys from Nucky Thompson and transporting it from Atlantic City to New York. Simon works with Davey Murdoch and several other men on this task. Murdoch and Simon take boats out to the Atlantic City Harbour and meet fishing Captain Bill McCoy. McCoy offloads a shipment of 100 cases of Canadian Club Whiskey onto their boat as Simon counts the cases. They take the whiskey back to shore and their men transfer it into trucks. Murdoch plans to drive through the night to get the whiskey back to New York.
The plan goes awry when the convoy is halted by an overturned car in the road. The car belongs to Billy Winslow who is also lying in the road. The obstacle is a trap set by hijackers Al Capone and Jimmy Darmody. When the hijackers open fire Murdoch and several others are killed but Simon escapes into the woods. Simon is pursued and shot by Capone. The shipment is stolen and taken to Chicago creating a feud between Rothstein and Nucky. Simon survives the hijacking and is taken to a hospital in Atlantic City in the custody of the Sheriff's Deputies. ("Boardwalk Empire")
Simon is wheeled into a Pennsylvania hospital by a pair of orderlies. His abdomen gapes open following the large shotgun wound he sustained in the Hammonton hijacking. A doctor and a nurse walk alongside the stretcher. Sherriff Eli Thompson is waiting in the corridor with a group of deputies as Simon is pushed past. Atlantic County Treasurer Nucky Thompson and Jimmy Darmody arrive behind Simon; Eli goes to greet them. Nucky asks how Simon survived three days in the cold of the woods and Eli guesses that Simon’s obesity protected him, immediately undermining his assumption by stating that he is not a doctor. Nucky is annoyed at Eli for stating the obvious and turns his glare on Jimmy, the architect of the hijacking. Jimmy tells Nucky he thought all of the men they hijacked were dead. Nucky criticises Jimmy for thinking, comparing him to the philosopher Aristotle. Nucky asks what the doctors are doing to Simon. Eli says that with Simon’s wounds the doctor’s interventions will be pointless. Nucky asks if Eli is now a doctor. Eli asks why Nucky is mad at him. Nucky ignores the question, checking his watch. He says he is running late and tells Eli to let Simon die naturally or to hasten his death if able. Nucky warns Jimmy to hope that Simon dies before he can reveal Jimmy’s involvement in the hijacking. ("Broadway Limited")
Eli watches as Dr Brubaker treats Simon. He asks the doctor to let him question Simon in private. Deputy Halloran guards the door and Eli pulls a screen between Simon and the next bed, telling the neighbouring patient to go to sleep. Eli takes Simon’s pillow and presses it forcefully over his face. Simon moans and struggles weakly; the other patient is startled by the sounds. Eli fakes questioning Simon while suffocating him but is interrupted by the arrival of Prohibition Agents Nelson Van Alden and Eric Sebso. Eli pretends he was making Simon comfortable. Van Alden flashes his badge and tries to question Simon. Eli claims Simon needs rest and refuses to let him be interviewed while in his custody. Van Alden claims that because Simon has been taken across the Pennsylvania border for treatment the case is now federal. Eli refuses to back down and Halloran shoos the agents away. Sebso accuses Eli of obstructing a federal investigation and Eli tells them to get a warrant. Van Alden asks Sebso to guard the witness and leaves. ("Broadway Limited")
Van Alden returns to the hospital with a group of men following him. He presents a piece of headed paper to Halloran claiming that it gives him custody of Simon. Halloran goes to make a phone call while Van Alden has Simon carried down to his car. Sebso complains about the risk of Van Alden using a falsified document. Van Alden gives the men cash; they are destitute and go straight to buy food. Sebso asks where they are going and Van Alden says they will take Simon to New York because he is one of Arnold Rothstein’s men. ("Broadway Limited")
As they drive North Van Alden has Sebso check Simon’s pulse – it is weak. Van Alden aims to get Simon to Bellevue in just over four hours but Sebso is doubtful Simon will survive that long. Van Alden instructs Sebso to keep Simon awake by slapping him and Sebso complies to no avail. They enter Raritan, New Jersey and resolve to find a doctor. ("Broadway Limited")
Van Alden and Sebso burst into the offices of a dentist, Dr Lissender, as he is treating a small boy. They carry Simon into the room and demand that the dentist revive him. Lissender sees that Simon is dying but offers to give cocaine (which he keeps as an anaesthetic) when Van Alden is insistent. He gives an injection into the only site he knows – the gums. Simon does not respond to the first dose and Van Alden impatiently instructs Lissender to give more. After a second injection Simon awakens. He speaks Yiddish in response to questioning and while Van Alden does not understand the boy’s mother, Mrs. Fishbaum, is shocked. Van Alden forces her to translate and finds that he was being insulted. Sebso, also a Yiddish speaker, chimes in with a minor correction. Van Alden sits next to Simon and asks where he wants to die. Van Alden plunges his hand into the shotgun wound and Simon screams in agony; Lissender is horrified. Simon admits that there were two young men and that one was named Jimmy. Van Alden describes Jimmy Darmody and Simon confirms the identification moments before his death. Van Alden recites a passage from Revelations. Sebso points out that Simon was probably Jewish but Van Alden continues as Halloran and more deputies arrive. After completing his prayer Van Alden tells Halloran that Simon is all theirs. Simon's identification later forces Jimmy to flee Atlantic City and Rothstein to order Jimmy's death. ("Broadway Limited")
|Season one appearances|
|Boardwalk Empire||The Ivory Tower||Broadway Limited||Anastasia|
|Nights in Ballygran||Family Limitation||Home||Hold Me in Paradise|
|Belle Femme||The Emerald City||Paris Green||A Return to Normalcy|