|死亡||Shot by Jimmy Darmody|
Charlie Sheridan (played by Frank Shattuck) was a Chicago-based Irish-American gang boss. He is the main rival of Johnny Torrio and his outfit for control of the Greek Town neighborhood during Season 1. He and his accompaning men are ultimately killed after a meeting by James Darmody and Al Capone alongside Torrio (who didn't shoot) thus ending their turf war.
Charlie Sheridan is a prominent gangster in Chicago with a reputation for seriousness. Sheridan grew up poor and faced anti-Irish-American sentiment as a child. He built up an extensive criminal empire, including the Greek town sector of Chicago. Sheridan and his gang had occupied Greek town since the time of Chicago outfit boss James "Big Jim" Colosimo. Following Colosimo's murder the new head of the Chicago outfit, Johnny Torrio, wanted to extend his own interests into Greektown.
Johnny Torrio sends his enforcer Al Capone to meet with Greek speakeasy owner George Anastos. Anastos buys liquor from Sheridan and when Anastos is reluctant to switch suppliers Capone beats Anastos and tells him to send Sheridan to the Four Deuces if he has a problem. ("Anastasia")
Sheridan arranges for a sit-down at the Four Deuces (which is a brothel owned by Torrio) to negotiate with Torrio. Capone greets Sheridan when he arrives; Sheridan is annoyed that Torrio is not there. Jimmy Darmody gives Torrio’s apologies and Capone says Sheridan should speak to him. Sheridan claims to be insulted and his enforcer, Liam, complains that the streetcars are not running due to the snow. Jimmy offers refreshments and Sheridan refuses. A prostitute (Pearl) enters and kisses Jimmy, telling him she is going to Chinatown. Capone asks after Anastos and Sheridan guesses that he is at the dentist. Capone says Anastos needs to learn some manners and Liam interjects that lots of people do. Capone rises to the subtle insult and Jimmy interrupts to explain the reason for the invitation and their desire to share territory in Greek Town. Sheridan says he is amused by the entitled attitude of New Yorkers. Capone points out that Jimmy is from New Jersey but Sheridan is disinterested. Capone tells Sheridan to stay out of Greek Town. Sheridan says they are already there and have been since James "Big Jim" Colosimo took over. Capone reminds Sheridan that Colosimo is dead and states that Torrio, a fellow New Yorker, is in charge now. Sheridan asks if there is room for negotiation and Capone invites an offer. Sheridan suggests 10% of their income and Capone demands 25%. When Sheridan accepts Capone senses weakness and tries to increase the split to 50%. Sheridan is initially incredulous but claims that he will accept to avoid trouble with Torrio and then leaves. Sheridan later sends Liam and two other men back to the Deuces to attack Pearl and shoot the place up. ("Anastasia") Pearl later commits suicide in despair over the injuries Liam inflicts. ("Nights in Ballygran")
Torrio wants to avoid war but Darmody and Capone convince him that this would appear weak. They arrange a second meeting, this time at a restaurant owned by Sheridan. They pretend to negotiate a truce but have actually bribed the coat check girl to help them conceal weapons. a massive shootout erupts, which results in the death of all of Sheridan's men and Sheridan himself when Jimmy walks over to him, after Sheridan had been wounded, and coldy tells him that Greek Town belongs to them now before shooting him under the chin, killing him.
- Liam: Enforcer (deceased)
- Al Capone: Rival
- Johnny Torrio: Rival
- Jimmy Darmody: Rival, killer (deceased)