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Jewish mob

    Arnold Rothstein 
Played by: Michael Stuhlbarg

"If I'd cause a stranger to choke to death for my own amusement, what do you think I'll do to you if you don't tell me who ordered you to kill Colosimo?"

https://static.tvtropes.org/pmwiki/pub/images/boardwalkempire16_1441.jpg
"Reputation takes a lifetime to build and only seconds to destroy."
A high-level Jewish gangster with his fingers in every pie in New York. He rigged the 1919 World Series and is being investigated for it, but is a much more level-headed crime boss than any of the others.

Tropes:

  • Affably Evil: He is a very polite, soft-spoken man who rarely raises his voice. He also runs a criminal empire and has no qualms whatsoever about having people killed.
  • All Men Are Perverts: Played with:
    • A notable aversion for the most part, he's nearly the sole male character in the show who is never shown as even interested in a woman apart from his wife, let alone sleeping around, keeping mistresses, or behaving like a sexist pig (as the majority of the other men on the show do). At least this is the image that he is careful to maintain.
    • While Nucky claims Rothstein's "dead below the waist", Rothstein does not claim himself to be faithful, only discreet.
    • When he has a meeting with Margaret in "White Horse Pike", he tells her not to worry, because he's a married man.
    • Eventually, his widow reveals that A.R. had several mistresses and assumes that Margaret was one of them.
  • Badass in a Nice Suit
  • Bad Boss: He is overall nice to his subordinates, but if anyone crosses him or plots against him, he shows his true colours.
  • Bad Guys Play Pool: A consummate player who likes to use billiard metaphors
  • Book-Ends: The first season had Arnold Rothstein as the Big Bad/Greater-Scope Villain. The Final Season had his proteges Lucky and Lansky as the Big Bad Duumvirate.
  • Broken Pedestal: For Lucky Luciano in Season 4.
  • Card Sharp: In the odd case that his natural ability is not enough.
  • Cavalry Refusal: He is unwilling to go to war with Joe Masseria (even after he okays Gyp's murder attempt against him) and refuses Nucky's appeal for help in "The Milkmaid's Lot". He later works a deal with Masseria in "Margate Sands" but Nucky, who has not forgiven Rothstein for his earlier refusal, uses it to set him up for trouble with both Masseria and law enforcement.
  • Crazy-Prepared: He even makes his henchmen take out life insurance policies with himself as the beneficiary, guaranteeing that he profits off their actions regardless of whether or not they die.
  • Deadpan Snarker
  • Dropped a Bridge on Him: While his death is a matter of historical fact, it was still rather jarring for him to die in the seven year Time Skip between seasons 4 and 5.
  • Even Evil Has Loved Ones: He has a rather cute interaction with his wife in season 2, in which she advises him about an upset stomach. Right after that, he's basically shown "putting on" the ruthless persona he displays at all other times.
  • Evil Lawyer Joke: Makes one when Fallon compliments him for his ability to lie before court.
  • Evil Mentor: To Luciano and Lansky.
  • Fatal Flaw: His greed, as well as his pride (shown in his "obsession with winning" as Nucky calls it).
  • Faux Affably Evil: He's always polite and well-spoken and particularly witty, but is utterly ruthless.
  • Fixing the Game: He fixed the 1919 World Series. The subsequent legal problems force him to seek the help of Nucky.
  • For the Evulz: Once made a man choke to death on a billiard ball his own amusement.
  • The Gambling Addict: During an unusual run of bad luck in "All In", his cool demeanor disappears and he comes out looking like this.
  • Gosh Dang It to Heck!: Unlike other gangsters, Rothstein noticeably avoids vulgarity.
  • Greater-Scope Villain: In Season 1, he backs the D'Alessio Brothers' bid to seize control over Atlantic City from Nucky Thompson.
  • Greedy Jew: He's called this a number of times by his antagonists.
  • Happily Married: Subverted. He and his wife Carolyn seem to have a very sweet relationship, but after his death she confesses that Arnold cheated on her and only left her buckets of humiliation.
  • Historical Beauty Update: The real Arnold Rothstein didn't fit the mainstream idea of "handsome," and was nowhere near as attractive as Michael Stuhlbarg is.
  • Historical In-Joke:
    • There are chips from the Brook Casino on his desk in "To the Lost", which was the real Rothstein's most infamous business venture.
    • In the pilot, Lolly Steinman believes that Rothstein is a gambling cheat and claims that if he was any other person he'd been dragged out of the casino and shot in an alley. Three guesses how the real Rothstein died.
  • Kick the Dog: He threatens Frankie Yale by claiming that he once forced a man to choke to death on for his own amusement, adding, "what do you think I'll do to you, if you don't tell me who hired you to kill Colosimo?" However, such behavior seems to be the exception rather than the rule for him; generally, he has a pragmatic approach towards violence (see Pragmatic Villainy for details).
  • Kosher Nostra
  • Manipulative / Magnificent Bastard
  • Non-Action Guy: Rothstein is never seen doing anything violent.
  • Nothing Personal: Has a mild dislike for Jersey/Nucky and calls him out on his cavalier behavior, but still wishes him good luck when he's refusing to help him, after pointing out he saw everything coming and that Nucky is just a convenience of geography and supply.
  • O.O.C. Is Serious Business:
    • Rothstein is not-so-cool when talking to you on the phone? No wonder Mickey Doyle shit his pants.
    • His veneer slips when he and Nucky discuss how to handle Gyp Rosetti.
      Rothstein:"Do you think I entered into this relationship because I value your companionship? You are a convenience of geography and supply. You promised a quantity and a price. You have failed to deliver. And now owing to your inability to handle your affairs in New Jersey, a state I have little interest in or affection for, you expect me to start a war IN NEW YORK? WHERE THINGS ACTUALLY MATTER!?"
    • When Rosetti starts ranting at the other gangsters in "Resolution", Rothstein just sits at the back with a huge grin on his face. He seems to find Rosetti's meltdown highly entertaining.
  • Out-Gambitted: By Nucky in "Margate Sands". After Rothstein gets word from Mickey Doyle that Nucky is in control of the Overholt distillery on behalf of USST Mellon, the biggest distillery in the country, he demands a whopping 99% of its benefits in exchange for convincing Masseria to withdraw his support from Rosetti. Masseria's support is bought by having Luciano arrested by crooked cops while dealing heroin in partnership with Masseria and confiscating his heroin, then offering Masseria a partnership as the only way to recover his investment. However, Doyle was actually acting on Nucky's behalf, and as soon as he closes the deal with Rothstein, Nucky rats out Rothstein to Mellon, who orders Rothstein's arrest.
  • The Plan: In Season 3, Rothstein refuses to finance Luciano and Lansky's latest heroin shipment; rather than waiting out like Rothstein wants, they go to Masseria and offer him the same deal along with information about Nucky's planned movement against him. Rothstein has Luciano arrested by crooked cops, and his heroin (which is actually Masseria's) confiscated. Rothstein then has the heroin shipped to his office, and offers Masseria to cut him as a partner in dealing his own heroin as the only way to recover his investment, while destroying Luciano and Lansky's reputation as partners in his eyes. In exchange, Masseria must agree to withdraw his support of Gyp Rosetti, which Nucky has bought by giving him a 99% share of the biggest distillery in the country. So in a single movement Rothstein punishes his minions for going their own way, makes money if Masseria refuses, and makes more money if Masseria accepts the deal, which he does. The only fault in his plan is that he didn't anticipate that Nucky was also planning on Rothstein doing this, and Nucky pulls his own strings to have Rothstein arrested in punishment for not supporting him earlier in his Mob War.
  • Pragmatic Villainy:
    • When it's in his interest, he is very willing to call off taking revenge and work with his enemies. Demonstrated with Nucky in season one and Masseria in season two.
    • He refuses to aid Nucky in a bloody war against Masseria, but only because he has little to gain from it.
    • When Luciano and Lansky propose him new criminal ventures -heroin trade-, the badness of drugs is not even an issue; he refuses to back them because the timing is awful for business, as there's a Mob War brewing in New Jersey.
  • Professional Gambler: And he wins loads of money that way because he is that damn good. On the other hand if he has a run of bad luck and starts losing, the professionalism starts to disappear and he begins to resemble The Gambling Addict.
  • Reasonable Authority Figure: Not a nice guy at all, but he is fairly protective of his associates and is willing to listen to and reward good advice.
    • Even Nucky turns to him for advice when things in Atlantic City turn bad. Rothstein could have held a grudge and said nothing but instead he gives him solid advice on how to approach the situation. Nucky is visibly impressed.
    • He's quite respectful and courteous in making a deal with Margaret.
  • "The Reason You Suck" Speech: Gives one to Nucky in "You'd Be Surprised", over his handling of Gyp Rosetti and his frivolous relationship with Billie.
  • Sesquipedalian Loquaciousness
  • Softspoken Sadist: Rothstein never uses profanity and almost never raises his voice.
  • Stepford Smiler / Slasher Smile: The more he smiles, the more one should worry they're in trouble.
  • The Stoic: That smile is just there to conceal anything resembling a real emotion. He even lampshades his nature during a fallout with Nucky, retorting that emotions are not a habit of his.
    • Not So Stoic: When Nucky beats him at poker, he starts losing his composure and by the end of the night it seems like he is about to assault the dealer but Meyer talks him down.
  • Straight Edge Evil: Doesn't swear, drink, or womanize (openly). He likes milk and cake, prompting Nucky to say that Rothstein "eats like a fucking child".
  • Surprisingly Sudden Death: Season 5 does a Time Skip past his 1928 death with only a brief mention of it, leaving anyone who doesn't know the history with no idea what happened.
  • The Teetotaler: He likes to stay sharp at the table.
  • Took a Level in Kindness: In a way. In season 4, his affability and civility comes off as much more genuine and friendly and less of a mask for his brutal and ruthless nature.
  • Trademark Favorite Food: Milk and cake, emphasizing his Straight Edge Evil nature.
  • Villainous Breakdown: In "All In".
  • Wicked Cultured
  • You Have Failed Me: There's definite hints of this in season 2, when after being displeased by Luciano and Lansky, he has them serve as muscle in transporting a liquor shipment. They begin to plan accordingly. It's finally done, non-lethally in "Margate Sands". The police that have arrested Lucky actually work for Rothstein, who steals Masseria's heroin back. When Lucky lashes out, saying he'd trusted Rothstein, Rothstein replies that for all of his effort in turning Lucky into something better than a hotheaded thug, Lucky's failed him. Rothstein tells Lansky that Luciano's position is his if he wants it, and Luciano goes over to Joe Masseria.
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    William "Bill" Fallon 
Played by: David Aaron Baker

https://static.tvtropes.org/pmwiki/pub/images/Bill_Fallon_BE_3984.jpg

"$80 per hour. Which also will buy you my uncanny ability to make friends with judges."

Arnold Rothstein's silver-tongued lawyer, tasked with keeping him out of being prosecuted for rigging the 1919 World Series. He returns in Season 2 to take Nucky's defense in his election-rigging case.

Tropes:

  • Amoral Attorney: While Fallon actively seeks to cultivate this image, his practice of bribing judges and tampering with witnesses render him more of a gangster with a law license as opposed to merely being a cynical litigator who offers his services to anyone for the right price.
  • Chessmaster Sidekick: To Rothstein, despite holding himself out as an otherwise respectable member of the legal profession.
  • Consummate Liar
  • Deadpan Snarker
  • Hyper-Awareness: Unlike Nucky, he notices that Harlan has something important to say, which turns out to be the key to destroy Randolph's attempt to use Van Alden as a witness. Granted, Nucky could have realized it by himself if he wasn't a jerkass, but it's notable that Harlan had been working in the house for almost a month by then and no one else had bothered to ask him either.
  • Only in It for the Money
  • Screw the Rules, I Have Connections!: Fallon has all the judges in New York in his pocket, and has a self-described "talent at winning over juries".

Morello Crime Family

    Joe Masseria 
Played by: Ivo Nandi

https://static.tvtropes.org/pmwiki/pub/images/masseriavwx20131_83191_4953.jpg
"On my streets: no coincidence."
The quintessential Old World mobster, Masseria is the ruthless, greedy Sicilian don of the Morello Crime Family (predecessor of the real-life Genovese crime family) that controls NYC's West Side. He is constantly harassing Luciano to join him, since he can't just fathom the idea of a Sicilian working with anyone but Sicilians, until he succeeds in bringing him over at the end of Season 3.

Tropes:

  • Appeal to Vanity: Gyp gets a second chance from Joe "the Boss" when he promises to make him Joe "the King".
  • Ascended Extra/Early-Bird Cameo: Masseria is an ominous reference to the other NYC gangsters through Season 2, but appears in only one scene. He has a pivotal role in Season 3.
  • Best Served Cold: Luciano remarks that Joe keeps talking about the day he's going to kill Nucky and that Masseria will wait forever to get his revenge.
  • Bilingual Dialogue: English/Sicilian.
  • Deadpan Snarker: Though he's usually blunt, he enjoys himself in his condescension towards Gyp Rosetti.
  • The Dreaded: He's the one kingpin that Gyp Rosetti actively fears. And anybody not named Benny Siegel or Salvatore Maranzano in Season 5 would prefer not to have problems with him.
  • The Don: He's the boss of the Morello gang, now known as the Genovese crime family.
  • Eloquent in My Native Tongue
  • Eye Am Watching You: He says this to Lucky at the end of their season 2 meeting - in Sicilian, so neither Rothstein nor supposedly Lansky could understand it.
  • Foregone Conclusion: Owen's attempt on his life is doomed from the start (the real Masseria survived numerous assassination attempts), and taking on Luciano as his dragon isn't going to end well for Masseria.
  • Gratuitous Italian: Masseria tends to speak a mix of Sicilian and English, often in the same conversations.
  • Greater-Scope Villain: He holds this position in Season 3 given that Gyp Rosetti, the story arc's Big Bad, and his crew constitute merely one of several gangs comprising his vast criminal empire. However, it is not until several of his men are annihilated while under Gyp's command that he begins to take a direct interest in plotting Nucky's demise.
  • Hypocrite: For all of his harping on Lucky for going into business with Jews, and all his racial slurs thrown toward Rothstein in particular, he doesn't seem to have a problem cutting a deal with Rothstein for Luciano and Lansky's heroin, to pay off their debt to him. Of course, he's getting a hundred thousand dollars worth of heroin out of the deal.
  • Jerkass
  • Large and in Charge
  • The Man Behind the Man: To Gyp Rosetti.
  • Non-Action Big Bad: While he's easily one of the most intimidating kingpins in the series, he is never seen hitting or shooting someone himself. However, given his position, as well as the respect and/or fear he is held by even the most menacing of mobsters, it is likely that this was not always the case, as he killed many to become a powerful mob boss.
  • Not So Different: His constant overtures to Luciano, who knows it's all hogwash and that Masseria would have him only as a pawn.
  • Offscreen Moment of Awesome: During what was planned as a Deadly Bath, Joe and his men somehow turn the tables on seasoned hitman Owen Sleater with a spectacular if gruesome outcome, off screen.
  • Politically Incorrect Villain: He is an anti-Semite, believing Jews to be passionless and untrustworthy. The fact that Luciano chooses to be business partners with Rothstein and Lansky disgusts him. And yet he's got no qualms buying heroin from the same Jewish mobsters he earlier insulted.
  • Pragmatic Villainy: Initially refuses to back Rosetti's war plans because there's nothing to gain from a new war, but this changes when Gyp convinces him the Italians will be encroached sooner or later if no action is taken. It's revealed later that a large sum of cash doesn't really appease Joe.
  • Proud Gangster Race Guy
  • Shown Their Work: Masseria speaks Sicilian, a dialect that is barely intelligible to speakers of Standard Italian.
  • Sound-Only Death: His fate. Luciano gets up and goes to the bathroom as Siegel and Tonino walk in, and we watch Luciano listen eagerly as the two assassins empty their guns into Masseria. He emerges as soon as the gunfire ceases.
  • We Can Rule Together: He wants Luciano to join him, but Lucky knows he's an old-fashioned Mustache Pete truly dead-set in his archaic ways of running the mob.
  • We Used to Be Friends: Not really, but Lucky grew up in a neighborhood controlled by Masseria and he knew him as a child. Masseria also likes to remind "Salvatore" of what a sweet kid he used to be.
  • You Have Failed Me: To Rosetti halfway through Season 3. Unlike most examples, Gyp manages to talk Joe into giving him a second chance. Which he quickly squanders.

    Gyp Rosetti 
Played by: Bobby Cannavale

"Nucky Thompson, Arnold Rothstein...Luciano and the [ Jews ] he runs with....I['ll] kill 'em all."

https://static.tvtropes.org/pmwiki/pub/images/20120921-bobby-306x-1348248508_1776.jpg
"Nothing's personal? What the fuck is life if it's not personal?!"

Giuseppe Colombano "Gyp" Rosetti is a particularly violent Sicilian gangster based in New York who goes to war with Nucky after being snubbed on a large deal in season 3. Given that he answers directly to Joe Masseria despite wielding complete authority over a sizable group of men and territory, he is implied to be a capo within the Morello Crime Family.

Tropes:

  • Ax-Crazy: His very first appearance establishes this.
  • Badass in a Nice Suit: Gyp takes some time to groom his own suits. During Easter he's interrupted while doing it and he just wears a wifebeater in the dinner with the family, in which he's mocked for being a Sharp-Dressed Man in love with his suits. Meaningfully, he's in disarray and shown wearing an A-shirt when he dies.
  • Bad Boss: He's at Voldemort and The Joker levels of willingness to brutally murder subordinates at the slightest provocation.
  • Battle Trophy: After he assaults Nucky's HQ at the Ritz, he plunders and keeps Nucky's desk as a war trophy.
  • Berserk Button: While any number of things could set him off, he especially hates condescension.
  • Big Bad: Of Season 3, and way more clear-cut than any of Nucky's previous nemeses. Joe Masseria is the Greater-Scope Villain.
  • Blatant Lies: Why, he's old D. L. Collingsworth and this is his gas station. They are out of gas. Seriously. That stuff pouring out of the gas pump? Nothing of importance.
  • Blue and Orange Morality: In "A Man, A Plan..." he feels the need to tell the world that he is the proud son of a brick-layer and that he has contempt for fishermen. He is that kind of guy.
  • Bodyguard Betrayal: In "Margate Sands", he is stabbed to death by his second, Tonino, while his other two remaining men watch without interferring.
  • Bondage Is Bad: He enjoys erotic asphyxiation.
  • Book-Ends: He's contemplating the Atlantic Ocean in his first and last appearances.
  • Bulletproof Human Shield: He uses the poor waitress he was having sex with as cover in "You'd Be Surprised".
  • Bullying a Dragon: His "Reason You Suck" Speech to the assorted gangsters is already bad, but directing a large and offensive portion of it to Arnold Rothstein does not seem particularly germane to Gyp's continued existence. A.R. downplays it when Gyp half-apologizes much later, but in any case, Rothstein puts a hit on him just after said apology.
  • Bunny-Ears Lawyer: Gyp is a shrewd tactician... and a violent, unstable psychopath. Masseria puts up with Gyp's "quirks" because of his loyalty and skill, but it doesn't take long before he threatens Gyp with a permanent form of retirement.
  • Cloudcuckoolander: Gyp has a tendency to show up in public settings with an off-putting accessory (dog, colonial general's hat, etc.)
  • Compliment Backfire: Nucky wishes him "good luck" in Italian, in deference towards Rosetti and his mother tongue. Gyp takes the note, "Bone For Tuna," as a poorly written and condescending gesture and goes ballistic over it.
  • Cruel Mercy/Bait the Dog: In "A Man, A Plan...". During one of his Disproportionate Retributions, Gyp buries alive Franco, the cousin of his second Tonino, in the beach leaving only his head out so he'll have a long, painful agony before dying of exposure or drowning with the tide. Tonino begs Gyp for mercy, leading Gyp to pick back the shovel... and crush Franco's skull until well after he dies. Gyp then tells Tonino that he owes him for sparing Franco the wait. Eventually, Tonino gets even in the season finale.
  • Deadpan Snarker: Has his moments.
  • Death by Irony: He's ultimately killed by Tonino, who did it out of threat to his life. In other words, his death was nothing personal.
  • Disproportionate Retribution: Rosetti is quick to reply in an exaggerated way to slights, some of which only exist in his mind.
    • He beats a mechanic to death with a tire iron for implying offhandedly that he was ignorant of car technology.
    • The Sheriff of Tabor Heights wishes Gyp good luck when Gyp is in a bad mood. Gyp douses him in gasoline and sets him on fire.
    • Gyp's response to a priest telling him to quiet down in a church is to beat the priest up and rob His church.
    • His response to Nucky causing trouble for his booze trade is to order the bombing of Babette's.
    • Tonino's cousin happening to know a little more about waves causes Rosetti to bury him neck deep in the sand to drown, and then, when Tonino protests, bash his head in with a shovel.
  • Dragon with an Agenda: Despite paying tribute to Joe Masseria, Rosetti often plots ways to expand his power and influence without his boss's knowledge. His operation in New Jersey is entirely his idea - and he gets nearly killed by his own boss for it.
  • Establishing Character Moment: In the first scene of season three, he beats a Good Samaritan to death for an offhand comment he takes as an insult.
  • Evil Sounds Deep: Bobby Cannavale's natural deep voice adds a level of menace to Rosetti that wouldn't be otherwise possible.
  • Expy: Rosetti's psychopathic behaviour is very reminiscent of Richie Aprile from The Sopranos. He also resembles Ralph Cifaretto, given that he displays a surprisingly high level of intelligence that is often undermined by his own obnoxiousness, fancies himself as a natural-born "warrior" due to his Italian heritage, and is depicted as being a sexual masochist.
  • Foil:
    • Nucky Thompson is a businessman who doesn't take things personally. Gyp... well, takes everything personally.
    • To Chalky White. Both men come from "poor but honest" backgrounds and have little to nothing in the lines of formal education, and don't like it when people look down on them for these features. They're also both feared and respected by the men they work with, but dominated (literally, in Rosetti's case...) by strong women at home. However, Chalky respects education and is only involved in organized crime to provide a good life/social mobility for his family, Gyp loves being a gangster, and plays out his resentment by sadistically toying with other people.
  • Gratuitous Italian: Though not to Masseria's extent.
  • Hair-Trigger Temper: Gyp's the kind of man who could find an insult in a bouquet of roses.
  • Handsome Lech: A relentless flirt; if he isn't macking on some lady or other, give him five minutes.
  • The Heavy: His actions drive the plot of season 3.
  • Henpecked Husband: While Gyp is quick to lash out savagely against almost everyone around him at the slightest provocation, he actually seems afraid of his hot-tempered wife, Giaconda. In "Sunday Best", he does little more than glare and grumble ineffectually at his spouse despite becoming increasingly agitated as she and her family relentlessly mock him, while begging Tonino to stay just so he isn't steamrolled over here.
  • Hidden Depths: Gyp is not entirely made of rage, he established himself as a successful businessman in the gap between seasons 2 and 3. "Spaghetti and Coffee" shows that he is smarter than he first appeared, and that he actually likes to test people by feigning ignorance rather than truly being uneducated. His acumen is made evident when he quickly exploits Tabor Heights' strategic relevance and is able to talk his way out of permanent retirement with "Joe the King".
  • Hot-Blooded
  • Hot Guy, Ugly Wife
  • In the Back: He's stabbed in the back by his own right-hand man.
  • It's All About Me: Despite professing unwavering devotion to Joe Masseria, Gyp has no regard for anyone or anything other than himself.
  • Jerkass: Rivals, if not exceeds Mickey Doyle in terms of how many people he's pissed off and wants him dead.
  • Jerk with a Heart of Jerk: Exemplified in "Bone For Tuna" and "Sunday Best".
  • Kick the Dog: A dog-kicker extraordinaire. Since he perceives anything as an affront, the punts are covered under Disproportionate Retribution. A unique example has him gleefully mocking Nucky over the death of his mistress, Billie, for which he was responsible.
  • Killed Mid-Sentence: And it's "Barney Google with the Goo Goo Googly Eyes," of all things, that he's singing when Tonino stabs him in the back. Oh, the indignity.
  • Large and in Charge: He towers over the rest of his crew and is even taller than his boss, Joe Masseria.
  • Large Ham: In all likelihood, Bobby Cannavale is still finding bits of scenery between his teeth.
  • Laser-Guided Karma: Stabbed in the back by the very men he had terrorised for an entire season..
  • Male Frontal Nudity: In "You'd Be Surprised", during Bugsy Siegel's failed hit. Considering he's just been in a gunfight and is covered in blood, there's a bit of Fan Disservice.
  • Mad Bomber: He blows up a restaurant full of people in an attempt to kill Nucky and Rothstein.
  • Manipulative Bastard: Throughout his appearances in the series, Gyp has proven himself startlingly adept at exploiting other characters' egos and underestimations of his own intelligence to his advantage. When faced with the prospect of being whacked by Joe Masseria's men due to his past failures, Gyp makes a succcessful appeal to Masseria's vanity which not only earns him an extended lease on life but Masseria's full backing in an all-out war against Nucky Thompson. Similarly, he deceives a cunning seductress like Gillian into believing he is a lovestruck Dumb Muscle wrapped around her finger so he can pump her for information to facilitate his conquest of Atlantic City.
  • Neighbourhood-Friendly Gangsters: Gyp, of all people, buys off Tabor Heights at $200 per citizen instead of merely relying on intimidation (although the implication is also there). He even enjoys himself with a friendly New Era Speech about the importance of reading!. And he cancels Bible Camp...
  • Nice Hat: Masseria calls him a "general", so Gyp steals a Revolutionary War general's tricorn hat to wear.
  • The Nicknamer: Dubs Gillian "Red" and "Strawberry". Luciano gets called "short pants".
  • No Celebrities Were Harmed: His Hair-Trigger Temper and sadistic personality is largely modeled off of Tommy DeSimone, an enforcer for the Lucchese crime family who also served as the Real Life inspiration for Tommy DeVito in Goodfellas. Similarly, Rosetti is also reminiscent of other bloodthirsty and homicidal figures in La Cosa Nostra such as Albert Anastasia, the notorious "CEO" of Murder, Inc., Roy DeMeo, Tony Spilotro, Carmine Galante and Vito Genovese.
  • Nothing Personal: Nucky tries to point this out, but for Gyp, everything is personal.
    Everyone's a person, though, right? (later) Nothing's personal? What the fuck is LIFE if it's not personal?!
  • Not So Different: Tries to use the non-white/wasp angle with Chalky, who doesn't fall for it.
    Gyp: We got a lot in common, huh? We both got left out in the sun too long. Maybe you a little longer, huh?
    Chalky: You just ain't done cooking yet, friend.
  • Obfuscating Stupidity: See Hidden Depths.
  • One Steve Limit: Averted. He and Masseria do share a common first name of "Giuseppe", but use different variations of it. Rosetti uses "Gyp" and Masseria uses "Joe".
  • Parental Neglect: He is not even sure of what his daughters' ages are.
  • Pet the Dog: He keeps the dog of the mechanic he kills on the road, and seems to genuinely like the animal. He bluntly gives the dog to Margaret but later recovers it and shows concern for the pet.
  • Politically Incorrect Villain: Much like Joe Masseria, Gyp is openly contemptuous of all non-Italians but seems to harbor a particularly virulent hatred towards Jews.
  • Proud Warrior Race Guy: Gyp likes to refer to Italians as conquerors and has showed contempt for the Irish, Jews and Italians who work for non-Italians.
  • Raised Catholic: Bows to the Almighty, but not even the Lord is safe from the wrath of good ol' Gyp, who beats up one of His priests and robs His church.
  • Rags to Riches: His family was so poor that he lived in a cave during his childhood. In the present day he's a well-off dandy.
  • "Reason You Suck" Speech: After he finds out that Nucky will not sell him any more liquor, he tells all the assembled gangsters exactly what he thinks of them.
  • Ruthless Foreign Gangsters: Born and raised in Sperlinga, Italy, he's a extremely violent and unstable gangster based in New York and who tries to conquer Nucky's turf.
  • Smug Snake: Despite proving to be an unexpectedly formidable adversary for the series' protagonists, his overconfidence in his own skills as a tactician as well as his vast underestimation of Nucky's resourcefulness leads to his downfall.
  • The Sociopath: A reputation-defending example (i.e.: one with many traits characteristic of narcissistic personality disorder). He consistently displays a pronounced lack of impulse control by spontaneously going from being seemingly charming and humorous to becoming paranoid and aggressive over the most trivial slight or inconvenience. Additionally, he displays no concern for the feelings or well-being of those around him, including his own wife and children, whom he regularly neglects to pursue his own ambitions and carnal appetites. Furthermore, even when in a "good mood", he delights in inflicting pain and suffering as well as sadistically intimidating others with the threat of violence. Consequently, in a show filled with sadistic killers and cold-blooded crime lords, he distinguishes himself as the most depraved and deranged character encountered in the entire series thus far.
  • Start My Own: His takeover of Tabor Heights was meant to simply force Nucky into selling him liquor directly rather than have Rothstein acting as a middle man. However, he soon realizes that he can start his own smuggling operation and supplant Nucky as Rothstein's main supplier.
  • Tall Darkand Handsome: Given his physical appearance and impeccable taste in fashion, he is certainly capable of evoking this trope. (See image). However, any charm he possesses proves to be short-lived once his more unsavory qualities become apparent.
  • Troll: Gpy feigns taking offense after seemingly construing Nucky's statement that men have come along way from "living in trees" to imply that he's comparing him to a monkey. However, he breaks the ice by performing a rather humorous ape impression that even Nucky finds amusing.
  • Tuneless Song Of Madness: After appearing to pull back from his Villainous Breakdown, he begins singing the Barney Google theme in an increasingly demented voice.
  • Undignified Death: Goes down in a beach, stabbed in the back by Tonino while urinating, yelling "Barney Google" after losing all of his men and Masseria's backing. Adding insult to injury, Tonino -who has plenty of reasons to kill Gyp- apologizes and all but states it's Nothing Personal, a motif hated by Gyp.
  • Villainous Breakdown:
    • While praying in "Sunday Best". It culminates with him punching a priest in the face, then robbing the church.
    • In "Margate Sands", after Masseria abandons him and Richard Harrow kills most of his remaining men, Rosetti imitates Nucky, rambles about a delusional plan to rebuild his criminal empire from nothing out west, and begins singing the Barney Google theme song maniacally until Tonino stabs him in the back mid-song.
      "Relax, it's a party. I'm making a big decision. From now on, I'm only selling hooch every other Thursday! Because I have important friends. I'm an important person. I have important garters, holding up my very important socks! Do you have any idea who the fuck I am? Do you? Do you! ... I'm Barney Google! With the googoogoogly eyes! And I never, ever, take anything PERSONAL!!"
  • Villains Want Redheads: Gyp specifically mentions Gillian's red hair as part of his attraction to her. He also keeps flirting with the redheaded waitress at the Tabor Heights diner, and when he hires whores, they tend to be redheaded.
    Gyp: (to Tonino) Which of them waitresses do you think is cuter?
    Tonino: The little one - with the bobbed hair.
    Gyp: I'm gonna fuck the redhead.
  • You Have Failed Me: Masseria tells him this in "Sunday Best". Gyp is given a second chance when he is able to talk his way out by making a point about encroachment and promising a pile of corpses to Masseria. Unfortunately, Gyp only buys himself some time. When he fails to deliver on his promise, Masseria finally sells him down the river.

    Tonino Sandrelli 
Played by: Chris Caldovino

https://static.tvtropes.org/pmwiki/pub/images/ToninoSandrelli_6535.jpg
"You know, I'm just asking."

Gyp's right-hand man and polar opposite. Much put upon.

Tropes:

  • All There in the Manual: His last name is not stated onscreen.
  • Affably Evil: All things considered, a pretty decent and reasonable guy. Especially compared to his boss.
  • An Offer You Can't Refuse: After surviving Richard Harrow's rampage on Rosetti's men at the brothel due to hiding in a closet, he is discovered later by Nucky and Eli, and allowed to live and leave town (permanently, or else Nucky will kill him himself) on the condition he murder Rosetti.
  • Apologizes a Lot: A life serving psycho Gyp Rosetti has reduced him to this. Hell, he apologizes even as he stabs him in the back despite the fact that Gyp had given him multiple reasons to do so at that point.
  • Been There, Shaped History: Although he's a fictional character, he's depicted as one of Masseria's killers in the season 5 premiere.
  • Best Served Cold: Nucky has him killed after a meeting next to a caricature of Billie Kent, who was killed in the bomb he set at Babette's eight years before.
  • Bodyguard Betrayal: He stabs Gyp in the back while he's taking a leak and singing loudly, then stabs him in the gut for good measure. He goes on to become Masseria's right-hand man, and eventually he and Benny Siegel assassinate Masseria.
  • Bumbling Sidekick
  • Butt-Monkey
  • Chronic Backstabbing Disorder: He manages a quite impressive amount of it in his relatively small amount of screentime. And oddly enough, it's not this that does him in, but something he did all the way back for his first boss.
  • The Consigliere
  • The Dog Bites Back: But takes no pleasure in killing Gyp, and only does it out of necessity.
  • The Dragon: Only in a The Consigliere quality, since Gyp is single-handedly more badass than Tonino.
    • Dragon Ascendant: Tonino becomes Masseria's right hand man after killing Gyp, a position far bigger than Gyp ever dreamed of.
  • Extreme Doormat
  • First-Name Basis
  • Foil: To Gyp.
  • The Generic Guy
  • Honest Advisor: Tonino tactfully tells Gyp how weakening was his mischief on Tabor Heights in regard to his New York operations.
  • Hope Spot: He is smart enough to realize that he is about to be on a receiving end of You Have Outlived Your Usefulness from Luciano and Lansky. When Nucky takes interest in what is going on in New York, Tonino jumps at the opportunity to get Nucky's protection and offers to work for Nucky. Nucky seems to seriously consider the offer and Tonino seems to have saved himself once again. Then Tonino realizes that their meeting took place in a restaurant with a memorial to Billie Kent, Nucky's mistress, who died when Tonino bombed Babbette's on behalf of Rosetti. Tonino is dead by the end of the episode.
  • Nothing Personal: Implied when he says "I'm sorry, I gotta" while he's killing Gyp, a very ironic touch.
  • Number Two: To Gyp. Becomes Masseria's right-hand man in season 4.
  • Punch-Clock Villain
  • The Quiet One
  • Red Oni, Blue Oni: Blue to Gyp's red.
  • The Starscream: In Margate Sands. He is forced to become one. Then again, Gyp had killed his cousin despite Tonino begging him no to.
  • The Stoic: Pretty much a job requirement.
    • Not So Stoic: He visibly tears up while watching Gyp split his cousin's head with a shovel. He also eventually stops putting up with Gyp's constant bullshit.
  • Rewarded as a Traitor Deserves: When he realizes he's in a precarious position in Season 5, Tonino attempts to jump ship to Nucky's side. However, Nucky is aware of the many bosses Tonino has (in one case literally) backstabbed, as well as his role in Billie Kent's death. Tonino is dead by the end of the episode.
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Five Points Gang

    Frankie Yale 
Played by: Joseph Riccobene
https://static.tvtropes.org/pmwiki/pub/images/Frankie_Yale_Boardwalk_9463.png
"You're singing a different tune from last time I come."

A Calabrian gangster established in Brooklyn and old friend of Johnny Torrio and the Capone brothers.

Tropes:

  • Affably Evil: Always polite and compromising. If he didn't kill people for a living he'd be the Nice Guy.
  • An Offer You Can't Refuse: Rothstein makes him one in order to make Yale tell him who ordered the death of Colosimo.
  • Deadly Euphemism: "Visiting a friend".
  • Evil Mentor: Served as one for the Capone brothers before Al came under Torrio's wing and moved with him to Chicago.
  • Old Friend: Of Torrio and the Capones.
  • Professional Killer: Hired by Torrio in the pilot to murder his boss, Big Jim Colosimo.

Harlem Mob

    Doctor Valentin Narcisse 
Played by: Jeffrey Wright

https://static.tvtropes.org/pmwiki/pub/images/valentinnarcissevwx2013_73221_980.jpg
"Only kings understand each other."

A Harlem crime boss who introduces himself as a philantropist and "doctor of divinity". He has deals with Nucky and Chalky in Season 4.

Tropes:

  • The Aggressive Drug Dealer: After getting his supply from Arnold Rothstein he manipulates Dunn Purnsley into selling heroin in Atlantic City behind his boss' back.
  • As the Good Book Says...: He's fond of quoting the Bible.
  • Asshole Victim: He is gunned down outside a church by Lucky's hit-men in El Dorado.
  • Bad Boss
  • Blackmail: He stops every act on The Onyx Club until Nucky and Chalky agree to make concessions for the death of his booking agent at the hands of Dunn Purnsley
  • Beard of Evil
  • Big Bad: Of Season 4 along with Special Agent James Tolliver as part of a Big-Bad Ensemble. While Tolliver initially poses the most imminent threat to Nucky Thompson and his associates, Narcisse's scheme to expand his influence into New Jersey ultimately becomes a catalyst for instability in Atlantic City thereby bringing him into direct conflict with Nucky himself.
  • Big Bad Wannabe: He has fallen into this trope by the time Season 5 rolls around. He talks a good game about upstaging the likes of Lucky, Meyer, and the rest of white-privileged society. Unfortunately for him, being Wicked Cultured and a Villain with Good Publicity aren't much use against aggressive mob expansionists whose policies boil down to shooting anyone in their way, even in broad daylight in the middle of an adoring public.
  • Boomerang Bigot: He shows contempt for interracial sex and blacks who work with white people. Yet he himself is very pale skinned and works with white people on a regular basis.
  • Boom Head Shot: He's shot several times by his assassins, before getting a final bullet to the head.
  • But Not Too Black: Like many other rich African-Americans seen in the series. He also shows contempt for the darker skinned Chalky White.
  • Character Tics: Whenever he no longer wishes to speak to someone, he turns to the side, crosses his leg, places his elbow on his knee, and put his hand to his face.
  • Creepy Monotone: The tone of his voice, thoughtfully measured and calculating, can come off as quite unsettling at times.
  • Dastardly Whiplash: The closest example in the series, down to the pointed mustache asking to be twirled - and he eventually does.
  • Dude Where Is My Respect: Narcisse doesn't like segregation. Not as much as because it treats blacks unfavorably compared to whites, as it is about how it treats him unfavorably.
    Where I come from there are no such things as niggers, Mr. Thompson, and I refuse to be treated like one.
  • Evil Counterpart: To Chalky White, of whom he also counts as a foil.
  • Evil Mentor: To Dunn Purnsley and Daughter Maitland.
  • Expy:
    • Fans have noted he's essentially a Harlem Renaissance-era Brother Mouzone from The Wire, especially given the similarities between Mouzone's line that the most dangerous thing in America is "a nigger with a library card" and Chalky dismissing Narcisse as "a nigger with a dictionary."
    • He's also been compared to Breaking Bad's Gus Fring as both are soft-spoken and sophisticated but ruthless villains who operate illegally under the facade of legitimate business. Though a key difference between them is that Gus' politeness was genuine whereas Narcisse's is an act.
    • He's basically an evil version of W.E.B Du Bois. Both are light-skinned and highly educated black civil rights advocates who show a fierce pride in their race through social action and artistic expression. Narcisse wears the same Van Dyke and pointed mustache that Du Bois wore for most of his life.
  • Faux Affably Evil: Don't get fooled by his polite manners. He's bad.
  • Foil: To Chalky White. Both are self-made gangsters. However, where Chalky remains in touch with his humble roots and looks out for the poorer African-American community, Narcisse looks down at the lower class, and sees them only as people to be exploited in the heroin trade.
  • Giftedly Bad: He fancies himself a great playwright. No one agrees.
  • Holier Than Thou
  • Humiliation Conga: He ends season 4 with J. Edgar Hoover personally forcing him to betray all his principles and rat out the politician he most admires. And he has to call Hoover "sir."
    • And then in season 5 he's put firmly under the thumb of Lucky and Meyer, having to clear all his business with them while pathetically talking about how he's going to rise against them one day. Not much later, he's assassinated in public on Lucky's orders.
  • Insistent Terminology: Doctor Narcisse.
    • He refers to all blacks as "Libyans" with seemingly academic assurance.
    • And everyone gets the Mr./Mrs treatment, even if he despises them.
  • It's All About Me
  • Large Ham: To an extent. At any rate he has a real theatricality to him and tends to be a bit overdramatic. He even dies overdramatically.
  • Life Embellished: His play Ominira is based on his "rescue" of Daughter Maitland as a child. In that version, the mother kills herself.
  • Malcolm Xerox: He sees himself as a "Libyan" nationalist and considers racial mixing as degrading.
  • Manipulative Bastard
  • Man of Wealth and Taste: He even adopts the dueling stance before shooting.
  • Morally Ambiguous Doctorate
  • Most Writers Are Writers: Playwriter of seemingly highbrow, anvilicious works about the improvement of the Libyans, aka negroes.
  • Neighborhood-Friendly Gangsters: His philantropist persona in Harlem, his own turf, which is interwoven with his aggressive but sneaky expansion to the Northside.
  • No Celebrities Were Harmed: Based on Casper Holstein, according to Jeffrey Wright, with influences from other prominent African-American thinkers and gangsters from the era.
  • Non-Action Guy: Usually, but as shown in "White Horse Pike", he carries a gun and knows how to use it.
  • Not That Kind of Doctor: He is not a medical professional, but a doctor of divinity.
  • No True Scotsman: According to him, there are plenty of "Libyans" that keep the race down and should be paid accordingly.
  • N-Word Privileges
  • Parental Substitute: To Daughter Maitland. One of the creepiest examples ever, since he became that after killing her mother in front of her, and tells her to this day that her mother is burning in Hell.
  • Politically Incorrect Villain: He is against race mixing and very racist towards white people (to the point of wiping his hand after shaking hands with Arnold Rothstein).
  • Punny Name: Well, he seems to love himself.
  • Rich Bastard
  • Screw the Rules, I Have Connections!: He is an ally of gangster Owney Madden, owns a piece of several African-American artists and as of "White Horse Pike" has established a business relationship with Joe Masseria and a political alliance with Mayor Bader.
  • Sesquipedalian Loquaciousness: Chalky notes his tendency to use big words, describing him as a "nigger with a dictionary".
  • Soft-Spoken Sadist: He's soft-spoken and polite, but he has a woman brutally murdered in cold blood in the first episode he appears.
    • O.O.C. Is Serious Business: After Chalky's failed assassination attempt, Narcisse, visibly rattled, yells at Nucky, raising his voice for the first time.
  • Villain with Good Publicity: He is visibly upset when Purnsley meets him in Marcus Garvey's office, since he's trying to keep his criminal dealings and his labor as a philanthropist in Harlem separate.
  • Visionary Villain / Well-Intentioned Extremist: He is a member of the UNIA-ACL and wants to improve African-American society at heart. In every other show he'd be the hero. That being said, he has no problem selling heroin to those he considers "lesser" Libyans and ordering a hit on a preacher who suspects him of such.
  • Welcome to the Caribbean, Mon!:
    • Chalky initially thinks he is from Jamaica, but he is from Trinidad.
    • The character was almost named "Calypso Pete".
  • What Do You Mean, It's Not Symbolic?: Seconds after quoting Ecclesiastes 1:4, "One generation passeth away, another generation cometh, but the earth abideth for ever," he is murdered on the orders of the ascendant Lansky and Luciano.
  • Wicked Cultured
  • Would Hit a Girl: He has Alma Pastor murdered, and brutally beats up Daughter Maitland when he finds out that she betrayed him. It's also implied that it's not the first time he beat her. Not to mention his outright murder of Daughter's prostitute mother right in front of her..
  • You Have Failed Me / You Have Outlived Your Usefulness: Alma Pastor was likely going to die no matter what she said.

    Daughter Maitland 
Played by: Margot Bingham

https://static.tvtropes.org/pmwiki/pub/images/daughter-maitland-1024_7021.jpg
"Spend your life walking over the world. Never find your place, 'cause there isn't one."

A jazz singer who performs at The Cotton Club in New York City; she acts in The Onyx after Valentin Narcisse gets a 10% of the establishment in Season 4. In "William Wilson", she is revealed to be a spy entrusted by Dr. Narcisse with the task of gathering information on Chalky's activities.

Tropes:

  • Beauty Is Never Tarnished: Averted. Dear God, and how! She's barely recognizable after Narcisse's beating.
  • Belligerent Sexual Tension: With Chalky White.
  • Blood Is the New Black: After Chalky is forced to kill a corrupt cop in the car they are moving in.
  • But Not Too Black: Like most of the performers at the Onyx Club, she's very light-skinned.
  • Cast the Expert: Bingham is a Broadway singer in real life.
    • The Cast Show Off: Two of Bingham's songs can be found on the released Season 4 soundtrack.
  • Conveniently an Orphan: For Dr. Narcisse, to raise the way a "real Libyian" should. He's the one that made her orphanhood possible too.
  • The Chanteuse: Sultry lounge singer? Check. Surrounded by an air of melancholy? Check. Involved with the villain? Check.
  • Commonality Connection: Her interest for Chalky doubles when she learns that he also lost a parent when he was young and has been on his own ever since, just like her.
  • Dark and Troubled Past: See Daughter Of A Whore bellow.
  • Daughter Of A Whore: Her mother was a prostitute who was killed "on duty" by Narcisse.
  • Fallen-on-Hard-Times Job: In season 5, we learn that after she left Narcisse, he had her blacklisted and she was forced to find work scrubbing toilets.
  • Honey Trap: Sleeps with Chalky in order to spy on him for Dr. Narcisse.
  • Made a Slave: In practice, by Narcisse. He abducted her as a child after killing her mother. Now he pimps her to other men in order to fulfill his agenda, and if she shows any kind of attachment to them he hits her.
  • Pretty in Mink
  • Rags to Riches: Part of her backstory.
  • Sassy Black Woman
  • Sex–Face Turn: She sleeps with Chalky so she could spy on him for Narcisse. However, when Narcisse sends Purnsley to kill Chalky, she ends up stabbing Purnsley in the back, saving Chalky's life.
  • Slap-Slap-Kiss: With Chalky in "The North Star".
  • Statuesque Stunner: Bingham even used to be a basketball player.
  • Stepford Smiler: Since Narcisse advises her to not let her "melancholy" take ahold of her.
  • Stockholm Syndrome: Narcisse killed her mother and abducted her. He then raised her with the promise that she might sleep with other men, but her heart would always be his. When he punches her face until it becomes unrecognizable, she still extorts Chalky to not kill him.
  • Unresolved Sexual Tension: With Chalky White. They Do.
  • Who Names Their Kid "Dude"?: Someone who could only think of Exactly What It Says on the Tin, apparently. It's revealed in "Havre Le Grace" that she was too young to remember her real name when she was adopted by Dr. Narcisse, so he simply named her Daughter. The show's writers may have been inspired by the legendary blues musician Son House.
  • You Have Failed Me: Narcisse bashes her face in after finding that he has lied about the Chalky/Dunn fight in her apartment.

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The Castellammarese Gang

    Salvatore Maranzano 
Played by: Giampiero Judica

"Kingdoms raise, kingdoms falls, pretenders reach for the throne, but only Caesar can rule, and the pretenders, fade away"

A Sicilian mob kingpin who controls the Williamsburg-based Castellammarese gang and an Arch-Enemy of Joe "the Boss" Masseria. He often fancies himself as the Mafia's version of Julius Caesar.

  • Affably Evil: A soft-spoken, easy-going mobster who tries not to take things personally, even after an assassination attempt.
  • Analogy Backfire: Likes to compare himself with Caesar. Nucky points out that Julius Caesar was backstabbed. And indeed, just like Caesar, Maranzano is betrayed by an ally and stabbed to death.
  • Arch-Enemy: Masseria saw him as a rival, hence why the Castellammarese War broke out.
  • Big Bad Wannabe: Fancies himself a highly sophisticated urban kingpin who's always one step ahead of his enemies. He's not.
  • Death by Irony: Maranzano, who idolized Julius Caesar, is betrayed and murdered by a gang of men with knives.
  • The Don: He's the boss of the Castellammarese gang, nowadays known as the Bonanno crime family.
  • Foregone Conclusion: Him taking Luciano as his Number Two didn't end well for Maranzano.
  • It's All About Me: After winning the Castellammarese War, he immediately declares himself the boss of bosses, reneging on the peace deal he made with Luciano. This causes Luciano to have him killed at the end of Season 5.
  • Offscreen Moment of Awesome: His triumph in the Castellammarese War. Only the ending is partially depicted in season 5 with the assassination of Masseria.
  • Remember the New Guy?: Attributable to the long Time Skip. He's introduced in the Season 5 premiere, at which point, he is the most powerful gangster of New York.
  • Underestimating Badassery: Much like Nucky and Masseria, he saw Luciano and Lansky as upstarts who are way out of their league. Those same upstarts manage to claw into Nucky's weak point and intimidate him into backstabbing Maranzano.
  • We Can Rule Together: Like Masseria before him, Maranzano wants Luciano to join him as an underling. But Lucky knows that he and Masseria are dead-set Mustache Petes who are unwilling to work with other ethnic gangs, let alone with fellow Italians.
  • Wicked Cultured: Frequently likes to compare himself to Caesar. He's also power-hungry, wanting to become the Mafia's overlord.
  • Wrong Genre Savvy: He seems to believe that the real players in gangster politics are the more eloquent, cultured individuals that stand out among the brutal hoodlums that resort to violence to solve their problems. Luciano and Lansky show him just how much culture and refinement matter in their world.

The Commission

    Salvatore "Sal" "Charlie" "Lucky" Luciano 
Played by: Vincent Piazza

https://static.tvtropes.org/pmwiki/pub/images/lucky-luciano-BE_1648.jpg
[He begins the series as Rothstein's number two, an angry, hot-blooded young man prone to violent outbursts. He soon develops a rivalry with Jimmy Darmody, which gets exacerbated when he begins spending his time by sleeping with Jimmy's mother Gillian. Seasons 2 and 3 see him try to climb the gangster's social ladder, first by getting involved in the heroin business, then a short lived agreement between he, Jimmy and Lansky to overthrow the old guard of Nucky and Rothstein, but when that quickly falls apart he continues working under Rothstein, despite Masseria attempting to recruit him. When Rothstein betrays him at the end of season 3, however, Luciano takes Masseria up on his offer, becoming The Dragon for Joe the Boss, albeit a Dragon with an Agenda, as he knows he can only go so far if he keeps working for Masseria...

Tropes:

  • The Aggressive Drug Dealer: He starts this aspect of his business during the series:
    • Spends most of season two trying to get Jimmy and Capone to sell heroin. He succeeds in bringing Rothstein into the heroin trade in "To the Lost".
    • Backfires on him in "Two Imposters"; Charlie attempts to cut a deal for five pounds of heroin to a friend of a friend. Turns out the guy is actually NYPD, and Charlie finds himself in handcuffs.
  • Awesome Moment of Crowning: Via Sicilian blood bond after he arranges Masseria's death.
  • The Bad Guy Wins: In "Friendless Child", Nucky surrenders and give all his Atlantic City holdings to Luciano.
  • Big Bad Duumvirate: With Lansky in season 5. Although Lucky does get more screen time.
  • Book-Ends: The first season had Arnold Rothstein as the Big Bad/Greater-Scope Villain. The Final Season had his proteges Lucky and Lansky as the Big Bad Duumvirate.
  • The Brute
  • Butt-Monkey
  • Call-Forward:
    • A number of Luciano's scenes with Joe Masseria foreshadow Luciano's eventual killing of Masseria for making attempts on his Jewish allies (Lansky and Siegel, particularly).
    • Luciano is also the one in "The Milkmaid's Lot" to ask Nucky how a four-city alliance of gangsters would work, foreshadowing the Atlantic City Conference.
  • Character Development: He is much more calm and calculating in Season 5.
  • Demoted to Extra: In season 4; despite this, he's still listed in the opening credits while Lansky, who has had far more screentime thus far, isn't.
  • The Dragon: To Arnold Rothstein in Seasons 1-3, Joe Masseria in Season 4 and Sal Maranzano in Season 5.
    • Dragon with an Agenda: Like his real-life counterpart, he did harbor ambitions of upstaging them, and by the end of season 5, he establishes a Commission to regulate the American Mafia's activities, with him becoming its first Chairman of the Commission.
  • Foil: To Jimmy. Number Two to a powerful man, hot-tempered, and involved with Gillian. Unfortunately, they're also both holding a grudge over the Gillian thing.
  • From Nobody to Nightmare: Like his real-life counterpart, he starts out as a young hoodlum working for Rothstein, works his way up to the criminal ladder, and by the end of Season 5, he has finally begun applying all the lessons that he's learned throughout a long lifetime as a gangster, and also applying lessons learned from seeing the rise and fall of his contemporaries.
  • Evil Mentor: He turned Lansky to the 'Dark Side' when they were children.
  • Faux Affably Evil: Becomes this by Season 5. He always talks in a cold and calm tone of voice when speaking to enemies or rivals, but it's clear that he's barely masking his contempt for his enemies or rivals.
  • Friendly Enemy: He and Jimmy team up at the end of "Age of Reason", due to Lansky's suggestion. He has aspects of this with Capone, too.
  • Foregone Conclusion: His break with Rothstein in season 4 and alliance with Masseria? It's not going to end well for Massseria.
  • Hair-Trigger Temper
  • Heterosexual Life-Partners: With Lansky.
  • Hot-Blooded
  • I Have Many Names: To the point that Jimmy (in S2) and Masseria (S3) lampshade it.
  • It Will Never Catch On: A cop tells this to Luciano in "Margate Sands", regarding Luciano himself:
    Pricks like you, they come and go. No one remembers them. The only thing that remains is the law.
  • Jerkass: Unlike his more polite (and intelligent) boss.
  • Male Frontal Nudity: In "Family Limitation".
  • Mistaken Identity: Mistakes Darmody's mother for Jimmy's wife and starts a romance with her. This spiteful plan turns out to be an Epic Fail when he learns of the real kinship.
  • My Ethnicity Doth Protest Too Much: Lucky is a Sicilian gangster working in a Jewish mob, something very unusual. This is why Masseria, the head of the Sicilian mafia, insists on trying to bring him back to his "people".
  • Only Known by Their Nickname: Very few people get to call him "Charlie" (Rothstein, Lansky, Gillian); everyone else uses "Lucky" or "Mr. Luciano". Even fewer people (Capone among them) call him by his birth name - Salvatore. Not that he particularly enjoys it:
    Luciano: What are you, my priest? Back off.
  • Rage Against the Mentor: When he discovers Rothstein's double-cross.
  • "The Reason You Suck" Speech: He attempts one on Rothstein, of all people, in the Season 3 finale. It needs more work.
    You fucking set me up. Who the fuck do you think you are? I worked for that! I busted my ASS for that! It was MY idea, MY deal. You did not lift a finger. Sit on your desk, making phone calls! I'm out there in the fucking world!
  • Red Oni, Blue Oni: Red to Lanksy (and Rothstein's) blue.
    • Though he and Lansky seem to have switched roles in Season 5.
    Lansky: I say we move now, just take him the fuck out.
    Lucky: It's too soon, we don't got the support.
  • Sir Swears-a-Lot: Nucky, himself no stranger to profanity, calls him on it.
  • The Starscream: Turning against Rothstein is really more Lansky's idea, but Lucky doesn't really protest too much and begins to embrace the idea.
    • To Masseria in the Season 5 premier, as he orders his death.
    • And to Maranzano too, in "Friendless Child", he strong-arms Nucky into ordering his death.
  • The Stoic: In Season 5. He shows no emotion and speaks in a quiet and calm tone of voice.
    • Not So Stoic: But his stoicism is broken as soon as Mickey Doyle starts talking.
    Mickey: I've been running that place the last seven years. You don't need to be throwing the baby out...
    Lucky: SHUT THA' FUCK UP! *Shoots Mickey in the throat"
  • Taught by Experience: By the time of the final season, Luciano has finally begun applying all the lessons that he's learned throughout a long lifetime as a gangster, and also applying lessons learned from seeing the rise and fall of other gangsters. As a result the final season shows him finally dropping his need to impress people, he's learned how to play his cards close to chest, who to trust and not trust, (notably, he refuses to get involved in an alliance with anyone who has ever backstabbed somebody before) he controls his temper, and he never makes a move without calculating it out and being sure it's going to work for him. This is why he winds up as the top man in the American Underworld at the end of the show.
  • Those Two Bad Guys: Not so much in season one, but in season 2, he and Lansky become this.
  • Took a Level in Badass: See Character Development.
  • Unwitting Instigator of Doom: His pursue of a heroin deal with Masseria ends resulting in Owen Sleater's death. And ultimately, of a lot of Masseria's men too.
  • Used to Be a Sweet Kid: According to Joe Masseria. Forgive us for doubting Masseria's sincerity. (According to Lansky, Luciano was a bully who beat him up for his lunch money).
  • Villainous Friendship: with Lansky
  • Vitriolic Best Buds: He's constantly needling Lansky:
    Jimmy: A lot has changed in a year.
    Luciano: Sure, Meyer's started to shave.
  • You Have Failed Me: Hits this with Rothstein in season three's "Margate Sands", when it's revealed his arrest was set up by Rothstein as punishment for going through with the heroin deal when Rothstein told him not to. Rothstein reveals his sadness that Charlie has apparently learned nothing from him in all the years he's been mentoring him.
  • Young Future Famous People

    Meyer Lansky 
Played by: Anatol Yusef

"Charlie and I have learned a great deal from Mr. Rothstein....but nobody wants to be in school forever."

https://static.tvtropes.org/pmwiki/pub/images/meyer-lansky-BE_3105.jpg
"All you have to do is recognize an opportunity."
One of Rothstein's two main enforcers, he instead relies upon his intelligence and guile (as opposed to brute force) to get ahead in the world of bootlegging. He's also got his own protege in Benny Siegel.

Tropes:

  • A Day in the Limelight: "All In".
  • All Jews Are Cheapskates: Wants very much to dispel this assumption, thinking that if he and Luciano carry around fake watches to sell, they'll look bad.
  • Avenging the Villain: A case where the original villain isn't killed: during "All In" Lansky painfully confesses to Nucky that he regards his father as weak, and possibly a coward, while at the same time defending Rothstein as a great man. (Which raises the question of whether some part of Lansky views "A.R." as a Parental Substitute.) During the course of the episode he has to watch as the "great man" is repeatedly insulted, demeaned, humiliated and defeated by a boorish anti-Semite in a game of poker, until finally Lansky has to all but drag a suddenly pitiable Rothstein away from the table, like the child of an alcoholic who needs to bring daddy home from the bar. Is it any wonder that Lansky later ambushes and delivers a No-Holds-Barred Beatdown to the other poker player?
  • Bastard Understudy: To Rothstein.
  • Beware the Nice Ones: Despite being far more diplomatic and level-headed than most of his criminal associates, he is nonetheless equally capable of startling acts of brutality when sufficiently provoked as witnessed in "All In".
  • Big Bad Duumvirate: With Lucky in Season 5.
  • Book-Ends: The first season had Arnold Rothstein as the Big Bad/Greater-Scope Villain. The Final Season had his proteges Lucky and Lansky as the Big Bad Duumvirate.
  • The Cassandra: Warns Luciano in "Two Imposters" that no matter how badly they need the money from a heroin deal to pay back Joe Masseria, cutting a deal with an unknown party is a bad plan. Luciano goes anyway and is arrested for drug trafficking.
  • Commonality Connection: Tries to use Yiddish as one with Rothstein, who sees right through the trick and lampshades it.
  • Dawson Casting: There is no way this guy is 18.
  • Don't Explain the Joke: Yes, he got it, thank you.
  • The Dragon: Becomes Rothstein's in Season 4.
  • Evil Genius
  • Evil Mentor: Despite his young age, he already has one disciple, "Benny" Siegel.
  • Face Palm: His reaction to Lucien D'Alessio taunting Jimmy in "The Emerald City" can only be described as this, even though his hands were tied.
  • Fake Guest Star: Yusef is still billed as a guest star, despite being as prominent to the main plot and having as much screentime as Piazza, who is main credited, from the second season.
  • Fake Nationality: Anatol Yusef is English of Turkish descent.
  • Faux Affably Evil: Lansky is excruciatingly polite to almost everyone. Even when what he really wants to do is beat them to death.
  • From Nobody to Nightmare: It's odd to think that a man whose introduction consisted of Chalky taunting him for his age will be one of the most powerful men in the United States in only a few years.
  • Heterosexual Life-Partners: With Luciano, since they met in school. Well, when Meyer was going to school, that is.
  • Historical Person Punchline: Introduced this way in "Home".
  • Jewish and Nerdy: In as much as a ruthless gangster can qualify as this.
  • Kosher Nostra
  • Non-Action Guy: Although "The Age of Reason" shows that he also knows how to use a gun, brains were the thing that got him out of trouble again. However, as witnessed in Season 4, he can be a highly vicious physical combatant when sufficiently angered.
  • Only Sane Man: He spends much of his time with Luciano and Benny as their voice of reason.
  • Pragmatic Villainy: Takes after his boss in this regard, believing that one shouldn't "let the past get in the way of the future." Even in "Margate Sands", when Rothstein reveals he's behind Luciano's arrest and has all their dope, Meyer admits he understands why Rothstein did it and stops Luciano's wrath because it will get them killed. When Rothstein behaves like a dick at a poker game, Meyer counsels A.R. to stop, but only because he's projecting an image of weakness in public.
  • Rage Breaking Point: An anti-Semite is making fun of Rothstein all through a long card game that goes badly for him. This causes Rothstein an uncharacteristic Villainous Breakdown and finally manages to send Lansky over the edge. The result isn't pretty.
  • Red Oni, Blue Oni: Blue to Luciano's and Siegel's red.
  • Sesquipedalian Loquaciousness
  • Smoking Is Cool: Just about everyone smokes, but it's Lansky who's frequently smirking and getting the better of someone while puffing on a cigarette. Probably as foreshadowing to his death by lung cancer.
    • Meyer's also shows off his smoke rings. He never comments on it, but he's showing off.
  • Stepford Smiler: Almost as much as his mentor, Rothstein. Though Lansky's are less evil and more "can't we all just cooperate and make money?"
  • Stiff Upper Lip: Displays this as a kind of Refuge in Audacity when dealing with other gangsters.
  • The Starscream: Believes he and Luciano - with the help of Jimmy and his associates - can overthrow the old guard of Rothstein and Nucky.
  • Those Two Bad Guys: He and Luciano are sliding into this in season 2.
  • Took a Level in Badass: We knew from season two that Meyer could use a gun, but "Bone for Tuna" has him shooting two of Masseria's goons in cold blood to save Benny's life.
    • In Season 5, he is much more outgoing and confident.
  • Tranquil Fury: Especially compared to the Hot-Blooded Luciano.
    "Fifty pounds. One hundred. Thousand. Fucking dollars."
    • Even moreso in "All In." During his brutal beatdown of the Anti-Semite in the back alley, he keeps up a steady stream of Yiddish, barely raising his voice or altering his tone, even as he beats the guy into a bloody pulp.
  • Verbal Tic: Says "yes" when he is trying to defuse a situation.
    Gentlemen, I'm running a business here! Yes?!
    Charlie, if you don't shut up, we are both dead, yes?!
  • Vitriolic Best Buds: With Luciano, especially considering how they met:
    Meyer: One day on my way to school, I got stopped by a gang of older boys. The leader said he wanted my lunch money. I told him to go fuck himself. He laughed, said he'd beat it out of me, so I spit in his face. He did beat me, they all did, and they took my money. Next day, same thing. I spit in his face and then we fought. The third day, the kid asked me to join his gang. The kid was Charlie Luciano, and that's how we teamed up.
  • Villainous Friendship: Type I with Lucky and Benny.
  • Wise Beyond Their Years: Well, he is supposed to be a teenager in the first two seasons.
  • Yiddish as a Second Language: In "All In" he even makes an entire (untranslated) rant in it while kicking the shit out of a guy.
  • Young Future Famous People

    Benjamin "Benny" Siegel 
Played by: Michael Zegen

https://static.tvtropes.org/pmwiki/pub/images/michael_zegen_BE_4567.jpg
"So, should I tell [Rothstein] to go fuck a duck?"
A teenaged hoodlum, working as a gofer for Lansky and Luciano. He's a bit strange, but watch out when he starts shooting people.

Tropes:

  • Affably Evil: He's a charming and funny guy until he starts shooting innocent people.
  • The Artful Dodger: He debuts as a 15-year old, yet hangs around gambling dens and gangsters.
  • Ax-Crazy
  • Berserk Button: As "Bone for Tuna" demonstrates, do not attempt to bully him.
  • The Brute: In Season 3.
  • Deadpan Snarker
  • The Dragon: To Lucky and Lansky in Season 5.
  • From Nobody to Nightmare: The kid making chicken noises? He's going to become one of the most feared mob hitmen in history.
  • Historical In-Joke: Luciano calls him a "crazy" little kid, but he's not quite "Bugsy" yet.
  • Hot-Blooded: Imagine what he'd do if Lansky wasn't there to rein him in.
  • Informed Ability: Despite his reputation as a ruthless assassin, he botches more contracts than he pulls off smoothly: he misses every shot he fires at Masseria's men in "Bone For Tuna", kills everyone but Gyp — including a woman and child — in "You'd Be Surprised", and is late arriving to Masseria's assassination in "Golden Days for Boys and Girls". He isn't present for Narcisse's assassination, but orchestrated the hit, and gets the timing wrong there too — Lansky says to finish it before the Commission meeting but Narcisse dies after it.
  • Karma Houdini: Benny is a remorseless murderer who never receives any comeuppance for his actions during the show's run. Granted, anyone who's familiar with the real Benny Siegel's history will know that he'll get what's coming to him later in life.
  • Kosher Nostra
  • Pity the Kidnapper: When he is kidnapped by Nucky in "Friendless Child", he sings bawdy songs in an obnoxiously-loud voice, that even Mickey Doyle finds annoying.
  • Plucky Comic Relief: The kid is witty, from his nonchalant inquiry of what Lansky and Luciano want him to do about Rothstein ("oh, so I should tell him to go fuck a duck?") to his mother-henning Lansky when told to go out and pick up some halvah ("that stuff'll rot your teeth"). His sense of humor is lost on Jimmy, however.
  • Professional Killer: For Lucky and Lansky in Season 5.
  • Red Oni, Blue Oni: Again, Red to Lansky's Blue.
  • Teens Are Monsters
  • Took a Level in Badass: "You'd Be Surprised" shows us a glimpse of the infamous hitman Benny will become - aggressive, bloodthirsty, and audacious. Though he's still got work to do - he doesn't get his target, Gyp Rosetti.
    • In Season 5, he is shown to be much more precise and efficient.
  • Trigger Happy
  • Would Shoot A Girl: When Rosetti uses the woman he's with as a Human Shield, Benny shoots her without hesitation. In season 5, Benny and another hitman ruthlessly gun down several prostitutes just to send a message to Narcisse.
  • Would Hurt a Child: While he's looking to you in the eye, pleads you to not shoot and has shown himself to not be a threat already.
  • Young Future Famous People


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