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The Darmody Family

    Jimmy Darmody 

James Edison "Jimmy" Darmody
"I'm what time and circumstance have made me."
Played By: Michael Pitt

"I'm nothing but a murderer. I'm going to Hell."

Smart and resourceful, Jimmy was the product of a relationship between his teenage mother and the Commodore. He was more or less raised by Nucky, who pressured him to pursue an education in Princeton, during which he also met his fiancée and later wife, Angela. However, he abandoned all of them to join the army during World War I and came back different - and a lot more ambitious.

  • A Pupil of Mine Until He Turned to Evil
  • Abusive Parents: As the series sheds more light upon his relationship with his mother, it becomes increasingly apparent that he was sexually abused by her frequently as a child. Additionally, he is implied to be largely neglected by his biological father, "Commodore" Kaestner. By the time Kaestner attempts to reconcile with his estranged son for his own selfish purposes, he ends up thoroughly corrupting Jimmy and destroying his relationship with his wife and child.
  • Amazingly Embarrassing Mother: Oh boy.
  • Affably Evil: He's an intellectual who is a good friend and tries to be a good father and husband, but he's also a cold-blooded killer.
  • Anyone Can Die: What better way for the show to make evident that it does not fuck around, but to kill off the second most prominent character in the second season?
  • Badass in a Nice Suit
  • Berserk Button:
    • People lying about military service/expressing "chickenhawk" attitudes seems to be this for him.
    • Never make lewd comments about Jimmy's mom. Or look at her lustfully. Or put your hand on her, one way or the other. In fact, just be very polite to her in his presence.
  • Big Bad: In Season 2. After being incapacitated by a stroke, 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.
  • Big Bad Wannabe: A 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 the latter's preoccupation with a federal prosecution set in motion by the Commodore. Upon alienating his father's wealthy backers, he seeks the support of out-of-state mobsters who 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.
  • Blood Brothers: With Richard Harrow.
    Richard: Would you fight for me?
    Jimmy: 'Course I would, right down to the last bullet.
  • Blood Knight: He has one hell of a sadistic streak, and tends to crave steak after a nice juicy kill.
  • Byronic Hero: He is essentially the embodiment of this trope.
  • The Chains of Commanding: He's incredibly dangerous in a brawl or gunfight, but he has nothing close to the talent men like Nucky and the Commodore demonstrate for management. During the brief period in which he thinks he's usurped Nucky as king of Atlantic City, he alienates existing allies left and right while failing to bring new ones into the fold, and botches every crisis that comes his way. By the time Nucky starts undercutting him via mass importation of Irish whiskey, he's already effectively a beaten man.
  • Character Tics: Darmody has a habit of clenching and unclenching his right hand whenever he is getting agitated and would like to deliver a No-Holds-Barred Beatdown on someone.
  • Clothes Make the Legend: His blue suit, a gift from Al Capone.
  • Dark and Troubled Past: And not just World War I either, we find out in "Under God's power She Flourishes" that he had sex with Gillian
  • Dawson Casting: Michael Pitt is 29 at the start of the series, Jimmy is 22-ish.
  • Death by Flashback: A lot of insight into Jimmy's backstory is given in the couple of episodes before his death.
  • Death Seeker: He went to the war expecting to die, and he goes to his final meeting with Nucky unarmed, despite knowing that it's a trap.
  • Decoy Protagonist
  • Deuteragonist: He was basically the second most important character in the first two seasons. Which makes it all the more shocking when he is killed at the end of the second season.
  • The Dead Have Names
  • Disproportionate Retribution: Don't hit him. You'll regret it.
  • Driven to Suicide
  • Evil Sounds Deep: Perhaps as a side effect of beginning to kill again after the war his voice starts to sound a lot deeper during his time in Chicago especially when compared with the first few episodes, where he sounds like a college kid.
  • Expy: Of The Godfather's Michael Corleone: He starts off as a sweet kid completly uninvolved in the mob lifestyle with a boss as a father (or father figure). Attends an Ivy League school. Goes off to war and comes back different. Commits a shocking act of violence when he gets home, in his case the woods massacre, and takes a sabbatical. Comes back with slicked back hair a full member of the organization. The only difference is his mother issues, which are vaguely reminiscent of another gangster.
  • Face Death with Dignity: Seeing as he knew what was going to happen when he told Harrow he didn't need him and went to meet Nucky without a gun.
  • Forgotten Fallen Friend: By some, apparently. Luciano mentions him to Capone in season 5 and Capone doesn't remember him by name.
  • From Camouflage to Criminal: Jimmy's path goes from being a soldier in WWI trenches to mob enforcer and, eventually, failing in his attempt to become an underworld boss.
  • Genius Bruiser: Nucky and Angela remind him constantly that he has the brains to be something better than a gangster, but he won't listen.
  • Guns Akimbo: In "The Age of Reason".
  • Hazy Feel Turn
  • The Heavy: In Season 2, Darmody is entrusted by his father,"Commodore" Louis Kaestner with overseeing his criminal empire in Atlantic City.
  • Hookers and Blow: Taken to an extreme in "Under God's Power She Flourishes". When the hooker part is played by your mother, you really have gone off the deep end.
  • Hot-Blooded: A bit of a hothead since the beginning, but gets more and more so as the series goes on.
  • Hypocrite:
    • Probably because of the attitudes of the time, he has no problem cheating on Angela while he is away and even considers abandoning his family altogether and moving to California before his lover dies, but he reacts violently when he merely suspects that Angela was having a relationship with a photographer while he was in the army. He is, however, surprisingly cool when he learns that she was actually seeing the photographer's wife.
    • While working as a bouncer in a Chicago brothel, Jimmy throws a customer out saying that "when the lady says to stop, you stop". The first thing he does after returning to Atlantic City? He forces himself on Angela until she surrenders and agrees to have sex with him.
  • Iconic Item: His knife.
  • Invincible Anti-Hero: He wins every fight that he's in, is never really touched in any confrontation and it's implied that he'd kick the asses of the historically based young gangsters, though this could be attributed to the tendency in historical fiction to make real life characters butt monkeys compared to stronger, smarter fictional characters. This is eventually subverted during his fight with the Commodore... who he still manages to deal with.
    • However, this only applies to physical fights; his attempt to take the power from Nucky ends with a catastrophic failure.
  • It Gets Easier: He says this about killing: "My first time I vomited after. Two days straight. Second time I didn't even think about it."
  • It's Personal: Pearl's death, which makes him decide to take down Sheridan's entire gang and kill the mook that personally targeted her.
  • Jumping Off the Slippery Slope / Took a Level in Jerkass: As soon as the Commodore is paralyzed and Jimmy takes the reins, he gets a lot more vicious and assholish.
  • Kick the Son of a Bitch: In "Under God's Power She Flourishes", emotionally broken and high on heroin, he attempts to choke Gillian after she insults and belittles the late Angela's memory.
    • When Commodore intervenes by stabbing him in the back with a spear, Jimmy turns the table, stabbing his father to death, albeit on his mother's instruction.
  • Knife Nut: Very skilled with his trench knife, he's very good at delivering a Slashed Throat.
  • Mama's Boy: In a not so healthy way.
  • Mommy Issues: While his parental substitute Nucky was decent enough towards him, James has a double or recursive Freudian Excuse; his real father raped Jimmy's orphan, teenage mother and in turn his mother invoked an unhealthy and incestuous relation with Jimmy. This forced him to drop out of college, join the Army and miss the chance of a normal life.
  • Mugging the Monster: He is the "victim" of one in "Ourselves Alone", and it ends exactly like you'd expect.
  • My God, What Have I Done?: In "Under God's Power She Flourishes".
  • No-Holds-Barred Beatdown: Pretty much any time a fight devolves into physical violence. Once he lays out the first punch, he just can't stop himself.
  • Oedipus Complex: He and Gillian are very close, and he only wants to take out his adopted father, Nucky, because Gillian insists he do so. Played up during "Under God's Power She Flourishes" when we flashback to Jimmy's time at Princeton to see that he and Gillian once had a drunken night of sex which drove Jimmy to join the army. The present day storyline of the same episode has Jimmy stabbing his biological father, The Commodore, and finishing him off at his mother's request.
  • Parental Incest: Once slept with his mother. He ended up running off to the military afterwards.
  • Passed-Over Inheritance: The Commodore never changed his will after finding out his faithful maid had been poisoning him. Jimmy tears up the will, after checking that it all goes to him/his son if the will isn't found.
  • Perpetual Frowner: The amount of times he smiles in the series is very minimal. It's almost like he's determined to let the world know how gangster he is.
  • Pet the Dog: His interactions with Richard and Tommy greatly humanize him.
  • Posthumous Character: His corpse is later dug up by the cops in 1924, which is able to convict Gillian of murder.
  • Punchclock Villain
  • Red Oni, Blue Oni: Blue, to Al Capone's Red. Then Red to Richard Harrow's Blue.
  • Red Right Hand: One of his legs is held together by a large metal brace due to a war injury. This eventually serves as a handy way to identify his badly decomposed body.
  • Returning War Vet
  • Self-Made Orphan: Halfway. He kills the Commodore when he tries to stop Jimmy from killing Gillian.
  • Shellshocked Veteran: Jimmy is so desensitized to violence by all of the killing he experienced and committed in the war that he has no qualms about becoming a gangster when he comes home. As he puts it: "I died in the trench, years back."
  • The Starscream: To Nucky, and later the Commodore (arguably).
  • Son of a Whore
  • Start of Darkness: The second season episode "Under God's Power She Flourishes" flashes back to his time at Princeton culminating in an incestuous experience with his mother, which lead him to join the army.
  • The Strategist: To Torrio in Season 1. He tries to be one for Nucky, but Nucky's actually a better planner than Jimmy is.
  • Suicide by Cop: After doing the best he can to settle things in his life, he goes unarmed to a meeting with Nucky, knowing that it's a set-up. His going to the war after that... incident with his mother could also be seen as this since Word of God says that he intended to die and was surprised when he came back.
  • Surprisingly Realistic Outcome: In the second season, Jimmy tries to rob Nucky of his position of power and run his criminal empire, unfortunately his ambition only got him so far. Jimmy's volitvity, rash actions, and ruthlessness isolated him more and more from his business partners, save for Harrow, and it costed him a lot. Including Angela, who Manny Horvitz killed when he didn't pay him the money he owed him.
  • Too Dumb to Live: A lot of examples can be pointed out, but Jimmy's biggest mistake was how he treated Horvitz. If he would have just paid him the five thousand dollars he owed, things might have went a lot differently for him.
  • Trauma Conga Line: The entirety of his mortal existence.
  • Unwitting Instigator of Doom: After meeting with Meyer and Lucky in New York City, Jimmy is mugged by a pair of men. He easily dispatches them with his knife. However, the two men were nephews of Joe Masseria who were sent to talk to Meyer about their gambling den in his territory. Masseria obviously assumes Meyer and Lucky had something to do with their deaths and Rothstein is forced them to pay Masseria two thousand dollars and 10% of their card games. Rothstein then decides to assign Meyer and Lucky as a protection duty on a liquor shipment which leads to the two of them plotting to overthrow Rothstein.
  • Used to Be a Sweet Kid: As Nucky constantly reminds him. Jimmy also appears as this sweet kid in Nucky's dreams, rather than the adult he became.
  • Villain Protagonist
  • Villainous BSoD: Hits this three times in "Under God's Power She Flourishes". First, he hits it in flashback: he was thrown out of Princeton, slept with his mother, and joined the army; then hits it after being informed of Angela's death in the present day; then again after attacking his mother and killing his father.
  • Woobie, Destroyer of Worlds: Slides into this in season 2.

    Gillian Darmody 

Gillian Darmody
"There was no one for me. No one coming to save me. There were things I had to do to survive."
Played By: Gretchen Mol, Madeleine Rose Yen (as a child)

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

Jimmy's surprisingly-young showgirl mother to whom he is a bit too close. While certainly an unconventional parent, she'll do everything for her son's well being - or what she thinks that is.

  • Absurdly Youthful Mother: Gillian is frequently mistaken for Jimmy's sister/wife, though this is justified because she gave birth to Jimmy when she was thirteen.
  • A Fool and His New Money Are Soon Parted: At the end of the second season, Gillian is left as the sole administrator of the Commodore's fortune. By the beginning of the third, she's running a brothel that serves drinks during Prohibition in Atlantic City... and she's losing money. She is then forced to take a loan, but since Jimmy's body was never found she only can do so after killing a stranger and passing his body as his. It only gets worse in Season 4.
  • Amazingly Embarrassing Parents: To Jimmy.
  • And Starring: Gretchen Mol gets the "with" credit in season two (only followed by Dabney Coleman), and the final "and" credit starting in season three.
  • Best Served Cold: She waited a long time to get revenge on the Commodore for raping her.
  • Bitch in Sheep's Clothing: Underneath a polite and vivacious surface, she's extremely warped and calculating.
  • Black Widow: She kills Roger directly and Jimmy kills the Commodore on her say-so, and she tries to kill both Lucky and Gyp.
  • Break the Cutie: Gillian's whole story in 1897 is this, thanks to Nucky and the Commodore.
  • Broken Bird
  • Bullying a Dragon: She seems to think that it is a good idea to threaten Richard Harrow when he won't let Tommy forget Angela.
  • Christmas Cake: She tried several times when Jimmy was young, but never got married.
  • Crucified Hero Shot: Adopts the pose when the Pinkertons ambush her and push her against the ground to keep her from punching and kicking. Although calling her a hero is being pretty generous.
  • Deliberate Values Dissonance: The scene in “Nights in Ballygran” where she offers to raise her grandson so Angela can live her life is loaded with this. She makes the kid sleep by giving him milk mixed with whiskey and chain smokes while babysitting him. Angela is outraged, but by the proposal only.
  • Despair Event Horizon: When Roy Phillips is revealed to be an undercover detective investigating Roger Mcallister's murder. Doubles as a Villainous Breakdown.
  • Evil Matriarch: Clearly slips into this by the end of Season 2.
  • Fallen-on-Hard-Times Job: In Season 4 she's been degraded from madame to whore and barely has any furniture left.
  • Faux Affably Evil
  • Femme Fatale: Could have cost Luciano too much if he wasn't "Lucky" Luciano. She is more successful with Roger, the hapless boy who just happened to resemble Jimmy.
  • Freudian Excuse: An orphan who was raped and impregnated at 13.
  • Functional Addict: In Season 4 she's developed a heroin addiction after Rosetti injected her with the heroin she tried to use on him.
  • Go Among Mad People: After she's convicted of killing Roger, her lawyers use the defense that she committed the act in a state of temporary insanity. As a result, she ends up in a mental institution by Season 5, and is desperate to assure the staff she's cured now.
  • Green-Eyed Monster: She is jealous that Richard has a better relationship with Tommy than she does and she eventually kicks him out when, among other reasons, she thinks Richard's girlfriend will supplant her as a maternal figure to Tommy.
  • Green-Eyed Redhead
  • Heel–Face Door-Slam: She overcomes her heroin addiction, makes peace with Richard, and is ready to start a new life with Roy. Then comes The Reveal that Roy is a Pinkerton, investigating her for murder of Roger Mcallister.
  • He's Just Hiding!: In-universe, this is her public reaction to Jimmy's death.
  • Hoist By Her Own Petard: Tries to kill Gyp Rosetti using the seduction followed by heroin injection method she used on Roger the Jimmy look-a-like, but he catches her, and promptly injects her instead. She at first appears to die from it, but is later found utterly strung out in the hallway by Nucky and Eli. The next season reveals that she's still addicted to it eight months later, having lost everything to the habit.
  • Hypocrite: In "Erlkönig", she confesses to be terrified that if Tommy is raised by other woman he'll forget her and it will be as if she never existed. Uh, remember what were you planning to do with Angela until last year, Gillian?
  • Kick the Dog:
    • One after another in "Under God's Power She Flourishes", all the way to the Moral Event Horizon and beyond.
    • In "Two Impostors", after finding out about Richard's relationship with Julia (and that Richard has taken Tommy to meet Julia), she tells Richard that he will never be able to find love, accuses him of not being fully human and orders Rosetti's men to remove him from the brothel.
  • Lady Macbeth: She becomes this for the Commodore, and then Jimmy himself, in season 2.
  • Mama Bear: A very twisted example towards her son, Jimmy, and her grandson, Tommy.
  • Miss Kitty: Season 3 finds her running a high-class brothel.
  • Ms. Fanservice: The second most frequent source of nudity in the series, after Lucy.
  • Mrs. Robinson
  • My Beloved Smother: To Jimmy. Also a beloved grand-smother to Tommy.
  • Parental Incest: As season two goes along, the hints of Incest Subtext increasingly become text. Finally confirmed in "Under God's Power She Flourishes."
  • Pet the Dog: Ultimately allows Richard and Julia to take custody of Tommy, having seen that the two of them are married, have a house, and genuinely care for Tommy. Her last act with Tommy is to give him Jimmy's dog tags.
  • Playing Gertrude: Gretchen Mol is only 9 years older than Michael Pitt. Justified by the character's background.
  • Promoted to Opening Credits: In Season 2.
  • Pretty in Mink: When she has something on, it's usually furry.
  • Rape as Backstory: The Commodore is Jimmy's father. She doesn't regret having Jimmy but is biding her time to get revenge on the Commodore for raping her. He also resents Nucky for being the enabler.
  • Really Gets Around
  • Single Mom Stripper
  • Single Woman Seeks Good Man: The implication is that she has been going for this ever since Jimmy was born, albeit in a very deluded - and clueless - fashion.
  • Stepford Smiler: A terrifyingly delusional and detached one. Beneath her vivacious façade there is a very damaged person.
    • Not So Stoic: "Sunday Best" finally has her hitting bottom and admitting Jimmy is dead. Right before everyone discovers the body of the guy she's passing off as him.
  • Teen Pregnancy: In her Back Story. She was impregnated at 13.
  • Villainous Breakdown: A heroin-induced one in "Margate Sands", in which she regresses to childhood and rambles incoherently to Nucky.
    Gillian: Nucky, you came... I was good... I went upstairs like you said... But the man, he did a very bad thing to me... *cries*

    Angela Darmody 

Angela Darmody, née Ianotti
"At least we're finally being honest with each other."
Played By: Aleksa Palladino

Jimmy's wife and the mother of his son, Angela finds herself torn in many ways. She loves Jimmy, but his extensive trips away lead her to cheat on him with a female photographer. She loves her son, but frequently has tension with Gillian, who lives with them.

  • And Zoidberg: Angela too often gets the short stick of Jimmy's attention when compared to Gillian. In "Gimcrack and Bunkum", when Jimmy is forced to make a speech on the fly he lists the reasons that soldiers fought in the war as their mothers, their sons and their wives. In that order.
  • An Offer You Can't Refuse: After her attempt to leave Jimmy at the end of season one is busted, he threatens her indirectly to take Tommy away. By the beginning of season two they have married.
  • Break the Cutie: The downward spiral of her relationships with Jimmy and Mary. Evolves into Kill the Cutie later.
  • Bury Your Gays
  • Ethereal White Dress: Fittingly enough, she wears a white dress throughout "Under God's Power She Flourishes", the episode after she dies in "Georgia Peaches". Her last appearance is a flashback.
  • Gratuitous Italian: She speaks Italian in "A Dangerous Maid" with Al.
  • Housewife
  • I Have a Family: When she pleads for her life to Manny, she tells him that she has a child. Manny shoots her anyway.
  • Important Haircut: She cuts her long hair at the end of the first season to punish Jimmy.
  • I Never Got Any Letters: Her relation with Jimmy sours further while he is in Chicago because Van Alden is intercepting their mail.
  • Kill the Cutie
  • The Pollyanna
  • Sacrificial Lion
  • Slap-Slap-Kiss: When Jimmy basically forces himself on her after returning from Chicago.
  • Stuffed into the Fridge: Murdered by Manny to get back at Jimmy.
  • The Quiet One: On account of her rather depressing situation.
  • Unperson: After she dies, Gillian tries to make Angela's son forget that Angela ever existed and make him think that Gillian is his mother.
  • Wide-Eyed Idealist: She prefers to concentrate on her artistic career rather than seeking a job while Jimmy is away. Later, she accepts fleeing to Paris as soon as Mary proposes it, and she still retains a soft spot for her just because Mary sent her a postcard a month after dumping her in the last minute.
  • Women Are Wiser: Moreso in season two than season one, though she's still the one to worry about the practicality of things.

    Tommy Darmody 

Tommy Darmody
"I want to go home."
Played By: Brady and Connor Noon, Travis Tope

The son of Jimmy and Angela Darmody. Played by Brady and Connor Noon as a child and Travis Tope as a teenager.

  • Ambiguous Disorder: There is clearly something off with him in the 5th season and no doubt had a part to play in him deciding to shoot Nucky.
  • Best Served Cold: After spending season 5 in his employ, he's ultimately the one to bring down Nucky Thompson, in retaliation for leaving his grandmother in the asylum, and also most likely for killing his father (he mentioned that Gillian frequently spoke of Nucky to him, most of it probably not good).
  • Brainwashed: After his parents die, Gillian insists that she is his mother, wanting him to forget that Angela even existed.
  • Cannot Tell a Lie: Justified, since he's a little kid. He gets better at it as a teenager.
  • Cheerful Child: Originally. As a result of his traumatic experiences, he becomes rather quiet and shy. And ultimately vengeful.
  • Chekhov's Gunman: Literally in the series finale. Hope you didn't forget about him after the timeskip.
  • Children Are Innocent: Until they grow up anyway.
  • Disappeared Dad: Jimmy is absent for most of Tommy's life, which makes Tommy initially fearful of his father.
  • Family Relationship Switcheroo: Gillian raises Tommy as her own son. Seemingly, everyone around her finds it incredibly creepy, especially the ones with suspicions about Gillian's relationship with her real son.
  • From the Mouths of Babes: In the first season, Tommy points a photo of a couple to Jimmy and says that it is of "Mommy's kissing friend". Jimmy gives a brutal beatdown to the man. Tommy meant the woman.
  • Lonely Rich Kid: Largely Gillian's fault.
  • Heartwarming Orphan
  • Heroic BSoD: The Season 4 premiere reveals that he didn't speak for a month after the events in the previous episode.
  • Meaningful Name: His alias of Joe Harper in season 5 is a character from Tom Sawyer.
  • Morality Pet: Played with. He humanizes Jimmy who on the other hand is into crime in order to provide for Tommy. A complex example for Richard too.
  • Parental Neglect: Living in a bordello speaks ill of Gillian's "mother"hood. It gets worse: Gillian's apparent idea of raising a child is keeping him to hers and limiting his contact with everyone else. And what's even worse, she doesn't seem to know what to do with the kid when she has achieved that, so she leaves him mostly to his own devices... and in a permanent state of loneliness. However, it would seem he was keeping in contact with Gillian while in the asylum, as he finally makes his move on Nucky right after he refuses to help her get out.
  • Parental Substitute: Gillian, followed by Richard and Julia. By season 5, he's seemingly out on his own and jobless. In the series finale, he tells Nucky he doesn't have a family after being told to go home to them (no thanks to him). There's never any indication of what happened with him and Julia. Of course, not having a family might have simply been a lie he told Nucky.
  • Primal Scene:
    • Witnesses a working girl in a bordello - who Tommy has a connection with - erm, "winning her bread." It was bound to happen sooner or later given that the boy lives in said bordello. It's malignantly invoked by one of the other girls.
    • Very narrowly averted in the first season, when Angela and Jimmy where at it while he was sleeping in a bed next to theirs. It probably helped their decision to buy a far bigger house in the next season.
  • Protectorate: Richard's. Of epic proportions.
  • Rags to Riches: One of the most heartbreaking versions out there.
  • Walking Spoiler: The series finale singlehandedly manages to turn him of all people into one.
  • You Killed My Father: In the finale, he takes revenge for his father and grandmother by shooting Nucky to death.


Miscellaneous Allies

    Richard Harrow 

Richard Harrow
"Would you pay a dime to see this?"
Played By: Jack Huston

A shy, socially stunted former World War I sniper who lost half his face in the battlefield and carries a tin prosthetic mask to hide what is missing. Very desensitized to violence, but at the same time craves human relations. He meets Jimmy at a military hospital in Chicago, and becomes his right-hand man.

  • Affably Evil: He's a sensitive and polite young man who is really likable. On the other hand, he's a ruthless killer and his suggested strategy for drawing out an enemy was to kill their innocent family members and associates.
  • Anti-Villain: Type II.
  • Anyone Can Die: His demise is the biggest example since Jimmy's death as he was arguably the show's most well loved and popular character at the time of his death.
  • Ate His Gun: In "Gimcrack and Bunkum". He gets better.
  • Background Halo: He gets one from a roof lamp when he meets again with Paul Sagorsky.
  • Battle Butler: He isn't quite a butler, but he serves as protector for the Thompson kids in season one and Tommy Darmody in season three.
  • Beauty Equals Goodness: Subverted. He is horribly disfigured but possibly the most moral criminal on the series.
  • Beauty Is Never Tarnished: So very averted.
  • Berserk Button: Disrespecting or hurting anyone close to him: Jimmy, Angela, Tommy, Julia...
  • Best Served Cold: He waited a year and a half, but in "Resolution" he finally gets revenge on Manny Horvitz for killing Angela. As a sniper he is trained to wait patiently to make his kills.
  • Beware the Nice Ones: Richard is easily one of the nicest, most genuinely thoughtful and caring people on the entire show. However, he has, by far, the highest individual body count of anyone in the entire series.
  • Breakout Character: Like Chalky White, his popularity in the first season made him quickly promoted to a series regular.
  • Blood Brothers: With Jimmy.
  • Boom, Headshot!: Most likely survived one in the First World War given his injuries. He in turn is very fond of dishing these out.
  • Cannot Tell a Lie: In his first scene, he claims not to be able to lie. Jimmy gets him to tell a small lie to the hospital staff, and a friendship is born. Since then, his scarce lies have been easily smelled.
  • Character Development: Richard debuts late in the first season saying that he does not believe that people can be emotionally connected to others, and offers to kill the innocent family members of the D'Alessio brothers just to force the brothers out of hiding. Throughout Season 2, Jimmy reassures him that their relationship is not strictly business but that he actually cares for him. Richard also genuinely connects with Jimmy's wife Angela and is hurt when she is killed by Manny Horvitz. In Season 3, Richard's main drive in life is to look after Jimmy and Angela's orphaned son Tommy. He avenges Angela's death by killing Manny, and even justifies this, differentiating between Angela and Jimmy's deaths - Jimmy was a soldier and knew what he was getting into by meeting with Nucky that night; Angela was an innocent who suffered needlessly due to Manny's Disproportionate Retribution. In Season 4 he returns to the family home in Wisconsin and confides to his sister that he is sick of killing and doesn't want to do it anymore.
  • Cleanup Crew: Twice in "Under God's Power She Flourishes". There's a straightforward instance at the end of the episode when Jimmy wakes up to see Richard cleaning up the Commodore's body and washing the blood off the floor, and a heartbreaking allusion earlier in the episode when Richard cries at finding Angela's blood still on the floor.
  • Cold Sniper: Very dispassionate and efficient when "working" even if he is a much nicer person than first impressions would indicate.
  • The Conscience: The one guy out of the Young Turks who will be completely honest with Jimmy, as well as question why Jimmy wants to do something.
  • Creepy Monotone: Richard always talks in a dispassionate manner, even when he offers to murder the family members of the D'Alessios or when he threatens to kill Paul Sagorsky.
  • A Day In The Lime Light: Season 2's "Gimcrack & Bunkum". He steps to the front and definitely becomes a main character from Season 3.
  • Diabolus ex Machina: At the end of season 4, it seems that Richard will finally have a family, something he always wanted. However, he has to perform One Last Job, and not only he misses his target, but he kills an Innocent Bystander and gets gunned down himself.
  • Disproportionate Retribution: In "Gimcrack and Bunkum", a crony of The Commodore disrespects Jimmy and bloodies his face. Harrow, under Jimmy's orders, scalps him.
  • The Dragon: To Jimmy.
  • Dramatically Missing the Point: Julia tells him that getting Tommy's custody would be easier if she was married. Richard asks "to whom?".
  • Driven to Suicide: Luckily for him, it gets interrupted.
  • Dying Dream: He makes it back to his old house, where his entire family is waiting. Then we see him with his whole face, and it turns out he's quietly bled to death at the spot where he first spent the night with Julia.
  • The Dying Walk: Although we don't get to actually see it, he walked away from the gunfight where he was mortally wounded all the way to the spot under the boardwalk where he and Julia spent their first night together, and then dies there.
  • Everyone Has Standards: While Eli doesn't even hesitate in suggesting they kill Nucky and Capone suggests Richard be the one to do it, Richard himself absolutely refuses.
  • Eye Scream / Facial Horror / Nightmare Face: There. Are. No. Words.
    • His face literally makes children cry (Emily cries hysterically when she sees him without his mask on in "Emerald City").
    • His jaw is so badly damaged he can't even bite an apple.
  • Face Death with Dignity: Mortally wounded, he makes his way out to the boardwalk and spends his last moments knowing that his family is safe in Wisconsin.
  • Freakiness Shame
  • From Camouflage to Criminal: He was a sniper in WWI, after the horrors of war and living with his PTSD and disfigurement, he falls back on those lethal skills to make a living.
  • The Grotesque: A very sympathetic version who you want to hug (at least when he's not killing people).
  • Guns Akimbo: His rampage through the Artemis Club in "Margate Sands".
  • Guttural Growler: Due to his war injuries, he talks in a gravelly, flat voice. He makes Tom Waits sound like a choir boy.
    • In one of the DVD commentaries, Jack Huston demonstrates the voice and talks about how he's had several people not believe it comes straight from him without electronic tampering.
  • Hand Cannon: When he is not carrying an actual cannon.
  • Handicapped Badass: Pretty much the poster boy for this trope.
  • Heroic Sacrifice: Not a conventional one but it's made clear that his rescue mission of Tommy and the subsequent killings had set him back to his state in Season 1 in terms of psychological health.
  • Hidden Depths: Is a fairly good dancer and has quite a sweet sense of humor.
  • Hitman with a Heart: Cold-blooded sniper who dreams of having a family and loves children. Deconstructed Trope: His inability to leave his assassination skills behind combined with his newfound humanity ultimately lead to his death.
  • Honorary Uncle: To Tommy.
  • I Just Want to Be Normal: Has a healthy envy of Jimmy's family life and longs to have one of his own.
    How does it feel, to have everything?
  • Improbable Aiming Skills: Justified in that Harrow is an Army-trained sniper. Still manages to pull off an impressive number of Boom, Headshot! moments, particularly in "Margate Sands," with handguns, a hip fired shotgun, and a non-aimed rifle. And all without depth perception.
  • It Gets Easier
  • It's Personal: He will wait as long as it takes to get his revenge. On the other hand, he sees no reason to seek revenge for things that occur as part of a war (or a Mob War) if no innocents were harmed. He takes bloody revenge for Angela's murder but sees no cause to avenge Jimmy's death. In his view there is nothing personal about soldiers killing and dying during a war. Similarly, Richard threatens Mickey Doyle after he takes credit for Manny's death at Richard's hands.
  • Kick the Dog: "I could kill their mother. The sisters. And the dentist. That would make [the D'Alessios] stick their heads up".
  • Lack of Empathy: Starts out like this. It's rather telling that out of a group of himself, Jimmy Darmondy, and Al Capone, the last two ruthless in their own right, Richard is the one who is sent to kill a fourteen year old boy.
  • Moe Greene Special: He is a rare, living, breathing example of this trope. Perhaps because of this, he's rather fond of dishing this out to enemies, as Liam, Manny and the poor bastards working for Rosetti can testify.
  • Morality Pet: To Jimmy. Angela, even after her death, Tommy, and Julia are his.
  • My God, What Have I Done?: His reaction to accidentally killing Chalky's daughter, which in turn leaves him too stunned to make a break for it after the hit on Narcisse goes wrong, resulting in his getting shot and eventually dying.
  • Never Speak Ill of the Dead: Even the people he kills still deserve respect, according to him.
  • Nice Hat: Favors a newsboy cap but wears a fedora when he asks Nucky for a job in season 4.
  • Ominous Walk: Tends toward these when "working".
  • One-Man Army: Pulls one off in "Margate Sands".
  • Papa Wolf: Harming Tommy is one of the quickest ways to get killed on this show. When his first attempt in getting Tommy out of the Artemis Club and Rosetti's hands fails, he returns in an epic rampage that kills almost all of Rosetti's men to get him back.
  • Parental Substitute: To Tommy, much to Gillian's displeasure.
  • Pay Evil unto Evil: His brutal murder of Manny Horvitz, his intimidation of Mickey Doyle and his full-out slaughter of Gyp Rosetti's men.
  • Promoted to Opening Titles: In the second season.
  • Red Oni, Blue Oni: Blue to Jimmy's Red.
  • Refuge in Audacity: He walks into Nucky's office holding Mickey Doyle at gunpoint and forces him to admit that Mickey's claims that he killed Manny Horvitz were false to Nucky. Why? Because Richard killed Manny for what he did to Angela, and he didn't want Mickey taking the credit.
  • Roaring Rampage of Revenge: Gillian kicking him out to separate him from Tommy was a really, really bad move. Richard tells her implicitly that he'll be back for Tommy. He comes back and despite there being a small army waiting at the Artemis Club, there is no amount of firepower that can keep him from Tommy.
  • Rule of Symbolism: Very often, Richard has his mask off when he is most vulnerable, or when someone discovers a facet of Richard they didn't know about.note 
  • Shellshocked Veteran: To the point where he's so desensitized to violence that he has no qualms about becoming a contract killer.
  • Shoot the Dog: When he returns to his childhood home, he finds the old family dog is terminally ill and dying so his sister requests that he put it out of its misery. It turns out he can't go through with it so his sister does it instead.
  • 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. Sometimes he is even accompanied by creepy organ music from the Phantom of the Opera. Like the Tin Man he has a metal face and believes wrongly, that he doesn't have a heart. He actually specifically calls himself the Tin Man once.
  • Shrouded in Myth: Seems to be heading in this direction after anonymously killing Manny Horvitz and 90% of Gyp Rosetti's crew.
  • The Stoic: To an absurd degree. This man just doesn't do much emoting and even when he does, it's hard to tell.
  • 10-Minute Retirement: In Season 4, he tells his sister that he is sick of killing and doesn't want to do it anymore. Unfortunately, he decides this after being paid to kill four men, and the employer is not too happy about it.
  • Throw It In: Jack Huston came up with Harrow's guttural voice himself, using Marlon Brando's cotton-in-the-mouth trick from The Godfather.
  • Too Happy to Live: In "Farewell Daddy Blues", it seems that Richard will finally be happy; with the help of Nucky, he manages to ensure that Gillian goes to jail, and he and Julia get the custody of Tommy. However, he has to perform one last job for Nucky in exchange. He botches it up, kills an innocent bystander, gets mortally wounded and dies soon after.
  • Tranquil Fury: His disfigured face and monotone voice makes it hard for him to express emotions so it's hard to tell when he is angry, with some exceptions:
    • When Gillian orders him to stop talking to Tommy about Angela you can feel the anger emanating from his body even though his posture and tone of voice never change.
    • The most visibly angry he's gotten is with Paul after he insults both him and his girlfriend, Paul's daughter. Even then, his voice was hardly louder than usual.
  • Two-Faced: Literally, and metaphorically.
  • Undying Loyalty: To Jimmy. Later passed to his son, Tommy.
  • Villainous Breakdown/Heroic BSoD: In Season 4, Richard's guilt finally catches up with him and he actually spares the life of man he was hired to kill after finding out he had a family. He futher breaks down when he can't even work up to the nerve to put a dying dog out of its misery and declares that he's done with killing.
  • Wild Card: Following the death of Jimmy.
  • Woobie, Destroyer of Worlds: You just want to hug him and let him know that it will all be right, but Holy Mother Of God will he bring down the thunder if you cross those that he cares for.
  • Would Mob Hit A Girl: Conversed with Jimmy. While he seems adamantly averse to laying hands on a woman, he is perfectly fine with dispaching them by other means if it serves the purposes of a Mob War. However, he undergoes much Character Development over the course of the series, and when he actually does shoot an innocent young woman by accident, he's absolutely horrified.
  • Would Hurt a Child: He shoots 14-year-old Pius D'Alessio to death, even though Pius tries to surrender. To be fair, despite his age, Pius wasn't an innocent child but a violent criminal.
  • You Are Better Than You Think You Are: When Richard attempts to paint himself as a monster for the massacre in the Artemis Club, Paul Sagorsky tells him that it makes him a hero because he did it all to save Tommy.
  • You Wouldn't Like Me When I'm Angry!: Piss off Richard enough and at best, you'll get off easy, as Paul did with simply getting beaten and choked. At worst, you'll find yourself like Manny Horvitz or like one of Rosetti's men, where having a 10/1 advantage will give you no good.

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