Jimmy Darmody

In January 1920, Jimmy has recently moved back to Atlantic City after recovering from his war injury. He displays signs of post-traumatic stress disorder from memories of the trench warfare and refuses to go back to school. He ends up working for Nucky as his driver and bodyguard. Frustrated that he is not doing more, he and Al Capone (Stephen Graham) hijack a shipment of bootlegged liquor that Nucky sold to Arnold Rothstein (Michael Stuhlbarg) and gun down the drivers. One of them survives long enough to identify Jimmy, but Nucky gets him out of trouble by blaming the hijacking on the deceased Hans Schroeder (Joseph Sikora) and sending Jimmy to Chicago.[5][6] There, he works for Johnny Torrio (Greg Antonacci) alongside Capone. When Nucky faces trouble back home from Philadelphia gangsters hired by Rothstein, he takes Jimmy back into his operation.[7]

Jimmy returns to Atlantic City with Richard Harrow (Jack Huston), a disfigured marksman whom he met in a military hospital in Chicago. They become close friends, with Richard becoming Jimmy's main ally in bootlegging. Jimmy also orders Richard to kill a rival gangster who had disfigured Pearl, a prostitute Jimmy was fond of, who become addicted to laudanum as a result of the attack and ultimately committed suicide while in Jimmy's care.[8] Jimmy reconciles with his father after the Commodore survives a poisoning attempt.[2] Jimmy is deeply hurt when he finds out that it was Nucky who arranged for the rape of his mother by his father, and plots with his father and Nucky's brother Eli (Shea Whigham) to take back control of Atlantic City from Nucky.[9]

By the beginning of season two, Jimmy is married to Angela, with whom he raises their son, Tommy. The Commodore has the New Jersey District Attorney's office arrest Nucky for election fraud and recruits Nucky's political allies. He and Jimmy then work on controlling the illegal alcohol being made and sold in Atlantic City.[10] When the Commodore suffers a stroke, Jimmy takes over his operations.[11] Jimmy is put in a difficult position when his partners in the bootlegging business — Capone, Lucky Luciano (Vincent Piazza) and Meyer Lansky (Anatol Yusef) — pressure him to kill Nucky. Though hesitant, Jimmy agrees to order Nucky's murder. Nucky is shot in the hand, but Clifford Lathorp kills the assailant before he can finish Nucky off. Jimmy is left wondering if he is doing the right thing.[12]

Jimmy enters a deal with Philadelphia gangster Manny Horvitz (William Forsythe) to supply him alcohol. Jimmy is short on cash and demands a $5,000 advance. However, Nucky has Owen Sleater (Charlie Cox), a former IRA assassin, blow up the warehouse where Jimmy's liquor is stored. Jimmy finds himself with no alcohol and thus no way to pay his debts. He ends up buying medicinal alcohol from George Remus (Glenn Fleshler) and uses it to make whiskey.

Nucky resigns as Treasurer of Atlantic County, and offers his surrender to Jimmy.[13] However, this is all a part of Nucky's power-play. He has Chalky White (Michael K. Williams), the leader of the black community in Atlantic City, to get all the black workers in the city to go on strike. The strike cripples the tourist economy that the city runs on. With help from Owen, Nucky then buys whiskey from Ireland and starts selling it in Atlantic City. Nucky's bootlegging operation flourishes, while Jimmy and his partners are left with an inferior product and nobody to sell it to.

Meanwhile, Jimmy grows tired of Horvitz asking him to repay his debts, and contacts Horvitz's rival Waxey Gordon (Nick Sandow) to have him killed. A few days later, Waxey's henchman attempts to kill Horvitz in his shop, and manages to wound him, but Horvitz fights back and kills the assailant by sinking a meat cleaver into his head. Figuring out Jimmy is responsible from a matchbook in the dead man's pocket, Horvitz plots his revenge.[14] Torturing Mickey for an address, Horvitz enters Jimmy's house, expecting to find him there. Since Jimmy is out of town, he instead finds Angela with her lesbian lover and kills them both.[15] Jimmy is devastated, and dulls the pain with alcohol and heroin. He attacks his mother when she talks about Angela's death nonchalantly. When the Commodore comes to Gillian's defense, Jimmy kills his own father, partially at Gillian's urging.[4]

Jimmy tries to make amends with Nucky, and he and Harrow help him with his election fraud case by killing the main witness for the prosecution, Alderman Jim Neary (Robert Clohessy), and staging it to look like a suicide. After the case ends in a mistrial, Nucky calls Jimmy and tells him that he has kidnapped Horvitz. However, Jimmy knows that he is being lured to his death, and willingly goes unarmed to see Nucky.[16] Jimmy tells Nucky that he truly died during the war, and even tries to talk him through the mechanics of shooting someone. Nucky shoots him twice in the head, killing him.[17]

Sixteen months after Jimmy's death, Nucky has a nightmare where he shoots an adolescent Jimmy below the eye (the same place Nucky had actually shot him).[18] By the beginning of season three, Gillian has not had Jimmy declared legally dead and runs the Commodore's mansion in Jimmy's absence. She turns the house into a high-class brothel and raises Tommy as her own. She eventually kills a man who resembles Jimmy and uses his body in place of Jimmy's, giving her control of the Commodore's estate until Tommy is an adult.[19]

In the season four finale, set two years after Jimmy's death, Gillian is put on trial for the murder of the man she claimed was her son in season three.[20] Richard, trying to keep Tommy out of her custody, testifies against her. However, without a body, Gillian faces little chance of getting convicted. Richard then strikes a deal with Nucky to anonymously tip off where Jimmy was buried. Jimmy's corpse is dug up and Gillian is convicted of murder.[21]