History Characters / BoardwalkEmpireDarmodyFamilyAndAssociates

* BigBad: In Season 2 by default. After being incapacitated by a stroke in Season 2, Jimmy's father, the Commodore, entrusts him with running his criminal empire and seeing through his plan to usurp Nucky's control of Atlantic City.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, Louis Kaestner "the Commodore", as an Atlantic City kingpin. Despite being a formidable player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does against Nucky Thompson due to [[WorfHadTheFlu the latter's preoccupation with a federal prosecution set in motion by the Commodore]]. [[spoiler:Upon alienating his father's wealthy backers, he seeks the support of out-of-state mobsters who [[AllTakeAndNoGive saddle him with debts he can't pay]]. Later, when Nucky floods Atlantic City with cheap Irish whiskey while orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to disappear. Ultimately, after his wife is murdered as a result of his shoddy business dealings, a grief-stricken Jimmy kills the Commodore before seeking peace with Nucky. For his trouble, he meets his death on account of two shots to the face.]]

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, Louis Kaestner "the Commodore", as an Atlantic City kingpin. Despite being a formidable player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does against Nucky Thompson only due to [[WorfHadTheFlu the latter's preoccupation with a federal prosecution the Commodore set in motion]]. [[spoiler:Upon alienating his father's wealthy backers, he seeks the support of out-of-state mobsters who [[AllTakeAndNoGive saddle him with debts he can't pay]]. Later, when Nucky floods Atlantic City with cheap Irish whiskey while orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to disappear. Ultimately, after his wife is murdered as a result of his shoddy business dealings, a grief-stricken Jimmy kills the Commodore before seeking peace with Nucky. For his trouble, he meets his death on account of two shots to the face.]]

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, Louis Kaestner "the Commodore", as an Atlantic City kingpin. Despite being a formidable player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does against Nucky Thompson only due to [[WorfHadTheFlu the latter's preoccupation with a federal prosecution the Commodore set in motion]]. [[spoiler:Upon alienating his father's wealthy backers, he seeks the support of out-of-state mobsters who [[AllTakeAndNoGive saddle him with debts he can't pay]]. Later, when Nucky floods Atlantic City with cheap Irish whiskey while orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to disappear. Ultimately, after his wife is murdered as a result of his shoddy business dealings, a grief-stricken Jimmy kills the Commodore before seeking peace with Nucky by wrecking his father's plot to have him prosecuted. For his trouble, he meets his death from two shots to the face.]]

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, Louis Kaestner "the Commodore", as an Atlantic City kingpin. Despite being a formidable player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does against Nucky Thompson only due to [[WorfHadTheFlu the latter's preoccupation with a federal prosecution the Commodore set in motion]]. Upon alienating his father's wealthy backers, he seeks the support of out-of-state mobsters who [[AllTakeAndNoGive saddle him with debts he can't pay]]. Later, when Nucky floods Atlantic City with cheap Irish whiskey while orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear. Ultimately, after his wife is murdered as a result of his shoddy business dealings, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky prosecuted. For his trouble, he is killed by two shots to the face.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, Louis Kaestner "the Commodore", as an Atlantic City kingpin. Despite being a formidable player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does against Nucky Thompson only due to [[WorfHadTheFlu the latter's preoccupation with a federal prosecution initiated by the Commodore]]. Upon alienating his father's wealthy backers, he seeks the support of out-of-state gangsters who [[AllTakeAndNoGive saddle him with debts he cannot pay]]. Later, when Nucky floods Atlantic City with cheap Irish whiskey and orchestrates a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear. Ultimately, after his wife is murdered as a result of his shoddy business dealings, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky prosecuted. For his trouble, he is killed by two shots to the face.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, Louis Kaestner "the Commodore", as an Atlantic City kingpin. Despite being a formidable player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does against Nucky Thompson due to [[WorfHadTheFlu the latter's preoccupation with a federal prosecution initiated by the Commodore]]. Upon alienating his father's wealthy backers, he seeks the support of out-of-state gangsters who [[AllTakeAndNoGive saddle him with debts he cannot pay]]. Later, when Nucky floods Atlantic City with cheap Irish whiskey and orchestrates a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear. Ultimately, after his wife is murdered as a result of his shoddy business dealings, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky prosecuted. For his trouble, he is killed by two shots to the face.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, Louis Kaestner "the Commodore", as an Atlantic City kingpin. Despite being a formidable player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does against Nucky Thompson due to [[WorfHadTheFlu the latter's preoccupation with a federal prosecution initiated by the Commodore]]. Upon alienating his father's wealthy backers, he seeks the support of out-of-state gangsters who [[AllTakeAndNoGive saddle him with debts he cannot pay]]. Later when Nucky floods Atlantic City with cheap Irish whiskey while orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear. Ultimately, after his wife is murdered as a result of his shoddy business dealings, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky prosecuted. For his trouble, he is killed by two shots to the face.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, Louis Kaestner "the Commodore", as an Atlantic City kingpin. Despite being a formidable player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does against Nucky Thompson due to [[WorfHadTheFlu the latter's preoccupation with a federal prosecution initiated by the Commodore]]. After alienating his father's wealthy backers, he seeks the support of out-of-state gangsters who [[AllTakeAndNoGive saddle him with debts he cannot pay]]. Later when Nucky floods Atlantic City with cheap Irish whiskey while orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear. Ultimately, after his wife is murdered as a result of his shoddy business dealings, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky prosecuted. For his trouble, he is killed by two shots to the face.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, Louis Kaestner "the Commodore", as an Atlantic City kingpin. Despite being a formidable player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does against Nucky Thompson only due to [[WorfHadTheFlu the latter's preoccupation with a federal prosecution initiated by the Commodore]]. After alienating his father's wealthy backers, he seeks the support of out-of-state gangsters who [[AllTakeAndNoGive saddle him with debts he cannot pay]]. Later when Nucky floods Atlantic City with cheap Irish whiskey while orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear. Ultimately, after his wife is murdered as a result of his shoddy business dealings, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky prosecuted. For his trouble, he is killed by two shots to the face.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, Louis Kaestner "the Commodore", as an Atlantic City kingpin. Despite being a formidable player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does against Nucky Thompson only due to [[WorfHadTheFlu the latter's preoccupation with a federal prosecution initiated by the Commodore]]. After alienating his father's wealthy backers, he seeks the support of out-of-state gangsters who [[AllTakeAndNoGive pressure him into needlessly escalating his war with Nucky and saddle him with debts he cannot pay]]. Later when Nucky floods Atlantic City with cheap Irish whiskey while orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear. Ultimately, after his wife is murdered as a result of his shoddy business dealings, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky prosecuted. For his trouble, he is killed by two shots to the face.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, "Commodore" Louis Kaestner, as an Atlantic City kingpin. Despite being a cunning and driven player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does in his conflict against Nucky Thompson [[WorfHadTheFlu due to the latter's preoccupation with being prosecuted]]. After alienating the Commodore's wealthy backers, he seeks the support of out-of-state mobsters who [[AllTakeAndNoGive pressure him into needlessly escalating his war with Nucky and saddle him with debts he cannot pay]]. Later when Nucky floods Atlantic City with cheap Irish whiskey while orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear as they begin rallying once more behind the Commodore. Ultimately, after his wife is murdered as a result of his business, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky imprisoned. For his trouble, he is killed by two shots to the face.

* CompletelyMissingThePoint: [[spoiler: Julia tells him that getting Tommy's custody would be easier if she was married. Richard asks "to whom?".]]

* BigBad: In Season 2 by default. After being incapacitated by a stroke in Season 2, Jimmy's father, the Commodore, entrusts him with running his criminal empire and seeing through his plan to neutralize Nucky.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, "Commodore" Louis Kaestner, as an Atlantic City kingpin. Despite being a cunning and driven player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does in his conflict against Nucky [[WorfHadTheFlu due to the latter's preoccupation with being prosecuted]]. After alienating the Commodore's wealthy backers, he seeks the support of out-of-state mobsters who [[AllTakeAndNoGive pressure him into needlessly escalating his war with Nucky and saddle him with debts he cannot pay]]. Later when Nucky floods Atlantic City with cheap Irish whiskey while orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear as they begin rallying once more behind the Commodore. Ultimately, after his wife is murdered as a result of his business, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky imprisoned. For his trouble, he is killed by two shots to the face.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, "Commodore" Louis Kaestner, as an Atlantic City kingpin. Despite being a cunning and driven player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does vying against Nucky for control of Atlantic City [[WorfHadTheFlu due to the latter's preoccupation with being prosecuted]]. After alienating the Commodore's wealthy backers, he seeks the support of out-of-state mobsters who [[AllTakeAndNoGive pressure him into needlessly escalating his war with Nucky and saddle him with debts he cannot pay]]. Later when Nucky floods Atlantic City with cheap Irish whiskey while orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear as they begin rallying once more behind the Commodore. Ultimately, after his wife is murdered as a result of his business, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky imprisoned. For his trouble, he is killed by two shots to the face.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, "Commodore" Louis Kaestner, as an Atlantic City kingpin. Despite being a cunning and driven player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does vying against Nucky for control of Atlantic City due to the latter's preoccupation with being federally prosecuted. After alienating the Commodore's wealthy backers, he seeks the support of out-of-state mobsters who [[AllTakeAndNoGive pressure him into needlessly escalating his war with Nucky and saddle him with debts he cannot pay]]. Later when Nucky floods Atlantic City with cheap Irish whiskey while orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear as they begin rallying once more behind the Commodore. Ultimately, after his wife is murdered as a result of his business, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky imprisoned. For his trouble, he is killed by two shots to the face.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 after succeeding his father, "Commodore" Louis Kaestner, as an Atlantic City kingpin. Despite being a cunning and driven player in the criminal underworld, Jimmy proves to be out of his depth as a politician and lasts as long as he does vying against Nucky for control of Atlantic City due to the latter's preoccupation with being federally prosecuted. After alienating the Commodore's wealthy backers, he seeks the support of out-of-state who [[AllTakeAndNoGive pressure him into needlessly escalating his war with Nucky and saddle him with debts he cannot pay]]. Later when Nucky floods Atlantic City with cheap Irish whiskey while orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear as they begin rallying once more behind the Commodore. Ultimately, after his wife is murdered as a result of his business, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky imprisoned. For his trouble, he is killed by two shots to the face.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 when he succeeds his father, "Commodore" Louis Kaestner, as Atlantic City's kingpin. Despite being a cunning and driven player in the criminal underworld, Jimmy reveals himself to be way out of his league when competing against the likes of Nucky Thompson. Upon assuming leadership of the Commodore's criminal empire, he quickly alienates its wealthy backers and loses their support. Faced with the loss of most of his father's political connections, Jimmy seeks the support of out-of-state mobsters who [[AllTakeAndNoGive pressure him into needlessly escalating his war with Nucky and saddle him with debts he cannot pay]]. Later when Nucky floods Atlantic City with cheap Irish whiskey while orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear as they begin rallying once more behind the Commodore. Ultimately, after his wife is murdered as a result of his business, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky imprisoned. For his trouble, he is killed by two shots to the face.

->''"I'm not allowed to speak! I'm not allowed to live! Why does a man get to do whatever he wants?!?!"''

[[caption-width-right:300:''"There was no one [there] for me.....There were things I had to do to survive."'']]

* Shout Out: Richards character greatly resembles The Phantom of the Opera and The Tin Man of Oz. He's a disfigured dangerous man in a partial prosthetic mask who desperately wants Love and companionship like the Phantom. Like the Tin Man he has a metal face and believes wrongly, that he doesn't have a heart.

* Shout Out: Richards character greatly resembles The Phantom of the Opera and The Tin man. He's a disfigured dangerous man in a partial prosthetic mask who desperately wants Love and companionship like the Phantom. Like the Tin Man he has a metal face and believes wrongly, that he doesn't have a heart.

->'''Played By:''' Aleksa Palladino

* {{Adorkable}}: His interactions with children, especially Tommy, and Julia.

* GoodAdulteryBadAdultery

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 when he succeeds his father, "Commodore" Louis Kaestner, as Atlantic City's kingpin. Despite being a cunning and driven player in the criminal underworld, Jimmy reveals himself to be way out of his league when competing against the likes of Nucky Thompson. Upon assuming leadership of the Commodore's criminal empire, he quickly alienates its wealthy backers and loses their support. Faced with the loss of most of his father's political connections, Jimmy seeks the support of out-of-state mobsters who [[AllTakeAndNoGive pressure him into needlessly escalating his war with Nucky and saddle him with debts he cannot pay]]. Later when Nucky floods Atlantic City with cheap Irish whiskey while simultaneously orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear as they begin rallying once more behind the Commodore. Ultimately, after his wife is murdered as a result of his business, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky imprisoned. For his trouble, he is killed by two shots to the face.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 when he succeeds his father, "Commodore" Louis Kaestner, as Atlantic City's kingpin. Despite proving to be a cunning and driven player in the criminal underworld, Jimmy reveals himself to be way out of his league when competing against the likes of Nucky Thompson. Upon assuming leadership of the Commodore's criminal empire, he quickly alienates its wealthy backers and loses their support. Faced with the loss of most of his father's political connections, Jimmy seeks the support of out-of-state mobsters who [[AllTakeAndNoGive pressure him into needlessly escalating his war with Nucky and saddle him with debts he cannot pay]]. Later when Nucky floods Atlantic City with cheap Irish whiskey while simultaneously orchestrating a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear as they begin rallying once more behind the Commodore. Ultimately, after his wife is murdered as a result of his business, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky imprisoned. For his trouble, he is killed by two shots to the face.

* BigBadWannabe: A [[DownplayedTrope downplayed]] example in Season 2 when he succeeds his father, "Commodore" Louis Kaestner, as Atlantic City's kingpin. Despite proving to be a cunning and driven player in the criminal underworld, Jimmy reveals himself to be way out of his league when competing against the likes of Nucky Thompson. Upon assuming leadership of the Commodore's criminal empire, he quickly alienates its wealthy backers and loses their support. Faced with the loss of most of his father's political connections, Jimmy seeks the support of out-of-state mobsters who [[AllTakeAndNoGive pressure him into needlessly escalating his war with Nucky and saddle him with debts he cannot pay]]. When Nucky later floods Atlantic City with cheap Irish whiskey and orchestrates a massive strike crippling its economy, his support among the city's ward bosses begins to rapidly disappear as they begin rallying once more behind the Commodore. Ultimately, after his wife is murdered as a result of his business, a grief-stricken Jimmy murders the Commodore before suing for peace by wrecking the latter's conspiracy to have Nucky imprisoned. For his trouble, he is killed by two shots to the face.