The Commodore's House
Louis "Lou" Kaestner a.k.a. "The Commodore"
- Big Bad: In Season 2. In the season's opening episodes, he masterminds a conspiracy to have Nucky thrown in prison but is incapacitated by a stroke before it comes to fruition. Subsequently, he largely delegates oversight over his plans to his son, Jimmy Darmody.
- Broken Pedestal: For Nucky, after the Commodore returns to the power plays.
- The Chessmaster: Even after thoroughly mentoring Nucky in the essentials for becoming a highly successful power broker in his own right, he still manages to catch his onetime apprentice offguard with a meticulously planned coup in the beginning of Season 2.
- The Collector of the Strange: Live and stuffed animals, weapons, Asian statues...
- Democracy Is Bad: Very dismissive about the average voter, whom he views as ignorant and unfit to have any kind of choice, although he doesn't care much for the suffragettes as long as they vote Republican.
- Dirty Old Man: When he was in his 50s, he impregnated a 13 year-old Gillian. He has not changed a little bit. The flashbacks in season 5 show us that he used to rape young girls regularly.
- Everyone Calls Him "Barkeep": Want to know his real name? Check the HBO website. Nucky, Eli, Gillian, and Damian occasionally call him "Lou", though it's very rare, and it's only once halfway through the second season when his full name is finally given onscreen.
- Evil Mentor: To Nucky, and later Jimmy.
- Evil Old Folks
- Expository Hairstyle Change: He stops shaving and combing his hair as he gets sicker in season 1. Then he feels healthier in season 2, so he dyes it. Then he suffers a stroke, so it is white again...
- Foreshadowing: His early season 2 speech about the stuffed grizzly bear.
- Great White Hunter: Was one when he was younger.
- Grumpy Old Man
- Hate Sink: He is easily one of the most unlikable characters in the show and a grade A asshole to everyone around him. Not only is he abusive, bigoted, racist and misogynistic, he is also an utterly loathsome pedophile and a serial rapist.
- He-Man Woman Hater
- Hypocrite: Recruits Jimmy and Eli to his conspiracy against Nucky using their bitterness over Nucky's dismissal of Eli as sheriff (which was the Commodore's suggestion) and Nucky facilitating Jimmy's mother's rape (by the Commodore).
- Impaled with Extreme Prejudice: Tries to do this to Jimmy. Fails.
- Jerkass: In the first season, he's unpleasant to pretty much everyone, and is one of the most bigoted characters in the show. It does seem that this had something to do with his illness since he comes across as rather avuncular and charismatic in the second season though he remains no less cruel and self-serving.
- Laser-Guided Karma: He gets so overexcited at the prospect of having sex with the adult Gillian that he suffers a stroke. This renders him mute and paralyzed, and then Gillian decides that it's time to get her vengeance.
- Manipulative Bastard: Ironically, some of the people he wins to his side are convinced by his claim that Nucky is a Manipulative Bastard.
- Nice Character, Mean Actor: Season 5 reveals him to have been this in his younger days. In the 1884 and 1897 flashbacks he is shown behaving in an avuncular and jovial manner in public, only to display his cruel and sadistic nature when in private. By 1919, after having lost his power and been in jail, he has dispensed with the pretense and is unpleasant towards virtually everyone. His pleasant facade returns somewhat in the second season after recovering from his illness.
- The Mentor: Straight example in his backstory. He teached Nucky everything about "the business" and Nucky inherited all that he now controls from the Commodore, in a deal the two made together for the Commodore to retire.
- This is, however, subverted in the season 5 flashbacks, where the late 19th century Commodore is shown to be mostly disinterested in young Nucky and quite the jerkass to him. The one that actually took Nucky under his wing was the Sheriff, Jacob Lindsay. The Commodore was an Evil Mentor, in the sense that he set Nucky with the example of corrupt boss to follow.
- Nice to the Waiter: Played with, his nastiness is showcased by the deplorable treatment of his maid who in revenge was poisoning him, causing his illness during the first season. Strangely, his will leaves most of his estate to the maid. He did not even change the will after he found out that she tried to poison him and she fled. This adds some significance to the Commodore's seemingly hypocritical line after learning about the poison.Commodore: Do you have any idea what I've done for you? Ignorant bitch!
- No Celebrities Were Harmed: His character is loosely based on Louis Kuehnle, a successful businessman who founded the Republican political machine which dominated Atlantic City for decades and was similarly known as "The Commodore" for owning a yacht firm. His personality also closely resembles that of U.S. President Theodore "Teddy" Roosevelt given his affinity for hunting as well as his enthusiasm for cultivating an image of robust masculinity despite his advanced age.
- Offing the Offspring: Attempted on Jimmy, though this was only in defense of Jimmy's mom, Gillian, after Jimmy started choking her for badmouthing Jimmy's deceased wife. Ironically, after Jimmy wounds him, Gillian is the one who encourages Jimmy to finish him off.
- Perfect Poison: Averted. His food, clothes and even toothpaste are poisoned with arsenic for almost a year and while his health worsens considerably he still survives.
- Pet the Dog: He showed a lot of affection to his dog Jerry. He also has an oddly ambiguous posthumous Pet the Dog when it's revealed that he left the entire estate to his maid Louanne, who had been poisoning him in return for his constant abuse.
- Politically Incorrect Villain: He's a vocal misogynist and a white supremacist.
- Rasputinian Death: It takes the better part of two seasons, and consequently most of his screentime. First he manages to survive prolonged cyanide poisoning over the course of Season 1, and recovers completely. After this he survives a stroke early in Season 2, which puts him largely out of commission, except for the occasional words of wisdom. Finally he is stabbed after a brutal melee struggle by Jimmy, who still has to deliver a Finishing Move before the Commodore is finally off his feet.
- Redemption Equals Death: Arguably. When he recovers his speech, he keeps secret the fact that Gillian abused him after he got paralyzed, suggesting that he was ashamed of what he had done to her, and he dies trying to save her when a drugged, emotionally broken Jimmy tries to choke Gillian. Ironically, Gillian is the one that convinces Jimmy to finish the Commodore.
- Retired Badass/Retired Monster: The previous owner of Atlantic City and the one who passed the torch to Nucky. He eventually tries to come out of retirement.
- Right-Hand Cat: Averted with Jerry, his little pet dog.
- Serial Rapist: Flashbacks in season five reveal Gillian wasn't his only victim, the Commodore was a frequent rapist of little girls.
- The Scrooge: Supposedly, he took care of Gillian, but she still needed to sell her jewels to pay for a roof. It's implied that he never got himself a family because he felt it would tamper with his 'reign' over the city.
- Sir Swears-a-Lot: He is probably the worst in a very bad mouthed cast. This could be due to his illness, his age, or most likely because he was always that way.
- Timeshifted Actor: Season 5 contains flashbacks to 1884, where a younger version of the Commodore is played by John Ellison Conlee.
- Took a Level in Badass: After he recovers from his illness, he exercises to the point of being able to lift a heavy elephant tusk over his head. Later on, despite still recovering from the stroke, he nearly manages to kill Jimmy, a man thrice younger than him and a war veteran, in melee combat after a surprise attack.
- Why Don't You Just Shoot Him?: He doesn't want Nucky killed, but to go to jail like he did.
- Blatant LiesHalloran: Arsenic was found in the Commodore's food, drinks, even the toothpaste. How do you explain this?Luann: I guess it musta fell in there somehow by accident.
- Foreshadowing: Looking back at Luann's first scene, there are numerous visible hints that she was poisoning the Commodore.
- Karma Houdini: The Commodore and Gillian see her as this. She did get away with attempted murder, but if ever there was an Asshole Victim, it was the Commodore.
- Mammy: Subverted. While she acts the part, Luann is actually quite crafty and has a far from benevolent agenda of her own.
- Perfect Poison: Averted. The Commodore still clings to life after months of continuous poisoning, and Luann eventually gets caught before the payoff.
- Put on a Bus: Nucky gives her money and tells her to skip town after her murder attempt is discovered.
- Timeshifted Actor: It is possible that she is a young maid seen in the Commodore's office in a Season 5 flashback, set in 1884.
- Unexpected Inheritance: The Commodore named her his heir before he recognized Jimmy and apparently forgot to change his will even after she was discovered trying to kill him. Jimmy then has the will destroyed.
- Why Don't You Just Shoot Him?: As illustrated by her quote, she takes the slow path with the Commodore because she regards the straightforward one as messy and impractical.
Leander Cephas Whitlock
The Commodore's long-term lawyer as well as an Atlantic City power-broker. He later serves as an advisor to Jimmy and (reluctantly) Gillian.
- Advertised Extra: Even if he has only one line, Dominic Chianese will be the first name you see in the closing credits.
- Amoral Attorney
- Best Served Cold: Betrays Gillian as revenge for her role in the Commodore's death, after pretending to be her ally for three years.
- The Consigliere: Used to serve as the Commodore's. Serves as Jimmy's, and reluctantly, Gillian's.
- Cool Old Guy
- The Mentor: Briefly, to Jimmy.
- Only Sane Man
- Punchclock Villain
- Red Oni, Blue Oni: The Blue Oni to Commodore Louis Kaestner's Red Oni. As Kaestner's most trusted aide and confidante, he serves as a voice of levelheadedness and pragmatism in stark contrast to his petty, megalomaniacal boss.
- Smart People Know Latin: He greets Eli with a Latin toast when he joins the Commodore against his own brother.
- Timeshifted Actor: His 1897 self appears in the Season 5 flashbacks, already working for the Commodore.
- Treacherous Advisor: To Gillian.
- Undying Loyalty: To Commodore Louis Kaestner. When the rest of the Commodore's backers abandon him shortly after he sustains a stroke, he alone stays to counsel Jimmy on ruling his father's massive criminal empire (despite being hindered at every turn by Gillian much to his chagrin). After witnessing the Commodore's ambitions go down in flames at the hands of Gillian, he obtains vengeance on behalf of his late friend by having her institutionalized.
- Worthy Opponent: He sees Nucky as this.
An Atlantic City veteran and war profiteer. He is part of a group of rich investors who back Commodore Louis Kaestner in his attempted political coup against Atlantic County Treasurer Nucky Thompson.
- Bigger Bad: In Season 2, he and a group of other extremely wealthy power brokers collectively fit this trope as the primary financiers of the Commodore's bid to seize power in Atlantic City. However, when Jimmy Darmody murders him in retaliation for an earlier physical altercation, they withdraw their backing.
- Bullying a Dragon: He first belittles Darmody's participation in World War I then goes so far as to strike the visibly unhinged war veteran in the head for his generation's "lack of respect." He is later killed for it.
- Evil Cripple: He's wheelchair-bound, but no less evil.
- Evil Old Folks: Parkhurst's age hasn't impeded his greed or temper.
- Grumpy Old Man: He views the current generation of Americans with barely concealed contempt (notwithstanding the fact that many of them died or experienced irreparable harm fighting for their country in World War I).
- Karmic Death: He is scalped to death; it makes sense since he participated in genocide against Native Americans.
- Politically Incorrect Villain: He takes great pride in participating in the U.S. government's genocidal campaign against Native Americans.
- Pet the Dog: Unlike the racist Commodore, he is portrayed as a surprisingly pleasant boss to his African-American butler, Alexander.
- Screw Politeness, I'm a Senior!: Despite his position as a member of the Atlantic City Memorial Committee, he dispenses with the formality of congratulating Jimmy Darmody for his service in World War and proceeds to rudely question him regarding the destruction of their alcohol warehouse as well as the unseen return on their investment. When Jimmy finally insults the men after enduring their berating, Jackson strikes him on the head with a cane.
- 0% Approval Rating: When he first appears, many of his colleagues seem to view him with contempt and disgust. Whitlock later states his death is unlikely to trigger much sympathy among his colleagues.
An Atlantic City power broker as well as one of several investors who bankrolls the Commodore's coup against Nucky in Season 2.
- Bigger Bad: In Season 2, he and a group of other extremely wealthy power brokers collectively fit this trope as the primary financiers of the Commodore's bid to seize power in Atlantic City. However, when Jimmy Darmody murders one of his colleagues, Jackson Parkhurst, in retaliation for an earlier physical altercation, they withdraw their backing.
- Evil Cripple: He uses an ear trumpet to compensate for his hearing loss. This handicap is later accentuated when he becomes visibly agitated when too many people begin talking for his liking.
- Evil Old Folks
- Faux Affably Evil: He initially acts very courteous and respectful towards Jimmy Darmody by commending him for his service in World War I. However, when the conversation turns to money, he joins in with his colleagues to berate Jimmy for failing to show them a return on their investment.
- Politically Incorrect Villain: He admits to using ties with the Ku Klux Klan to deal with the Commodore's "colored problem."
Sheriff Jacob Lindsay
- A Father to His Men / Da Chief: To Nucky in 1897.
- Bait-and-Switch: When he catches 12 year-old Nucky taking a bath in the Commodore's office's bathroom in 1884, it looks like he is going to punish him, but instead he takes Nucky and Eli to dine with his family and covers their absence to their father by telling him that Nucky is now working for him (Nucky's job as a bellboy in the Commodore's hotel had just ended with the tourist season). He finishes by offering Nucky to be his deputy in the future, which he accepts.
- Dirty Cop: The town wouldn't be complete without one.
- Dirty Business: He justifies being the Commodore's hatchet man because he sees it as necessary to keep Atlantic City going. However, when he has to cover up for the Commodore raping a young girl, he can's stomach it anymore and walks away.
- Everyone Has Standards: While he has done many despicable things for the Commodore, he has enough when he is called in to help cover up after the Commodore has raped a young girl. He gives his badge to Nucky and walks away.
- The Mentor: To Nucky, more than the Commodore. It seems that Nucky got the riches and power-hunger from the Commodore, and the idea that he could do unsavory things and still be a good husband and father from Lindsay.
- Nice Guy: Practically a saint compared to the men he hangs out with.
- Parental Substitute: To Nucky, to the point he cuts off all contact with his father when he becomes Lindsay's deputy.
- Professional Killer / Deadly Euphemism: What most "jobs" for the Commodore probably are.
- Rags to Riches: He was a carpenter's assistant when he met the Commodore. After doing two "jobs" for him, he was given the badge.
- Token Good Team Mate: In the Commodore's team. This eventually leads him to break with him.
- Screw This, I'm Outta Here! / Screw the Money, I Have Rules!: He effectively leaves his post to Nucky when the Commodore asks him to take a girl he just raped to her parents, and tell them not to make a scandal.
- The Consigliere: Seems to be this to the Commodore in 1884, spending most of the time next to him, and advicing him to pay his respects to Nucky's family when Susan dies so they remember when elections come.
- Jerkass / Jerk with a Heart of Gold: At least compared to the Commodore. Unlike him, he does warm up to Nucky over the years.
- Unwitting Instigator of Doom: How much of the series plot would actually have taken place, if he had not decided to prank 12 year-old Nucky by "losing" a hat with a 50$ bill (from 1884!), telling Nucky to retrieve it, and then telling him that he was not getting any tip for returning the money too?
- Sleazy Politician: Of course.
- The Starscream: Turns on the Commodore by 1897. While in a very softer way than most examples in the series (and out of it), it leads directly to...
- You Have Failed Me: ...the Commodore ordering him to be tied up and thrown off the pier to drown.