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Amsterdam
Amsterdam Vallon
Portrayed By: Leonardo DiCaprio
"It's a funny feeling being taken under the wing of a dragon. It's warmer than you'd think."
A thief of Irish origin, son of "Priest" Vallon, whom Bill the Butcher takes under his wing.
- Anti-Hero: Amsterdam is a petty criminal motivated by revenge and hatred, but the good person he truly is can't help but emerge.
- Beauty Is Never Tarnished: Bill the Butcher makes a big deal out of disfiguring Amsterdam, but only really keeps him a comparatively minor scar that doesn't impact DiCaprio's good looks. Otherwise, this is averted: his teeth are as grotesque as the other hoodlums.
- Becoming the Mask: He finds himself genuinely tempted by becoming Bill the Butcher's right-hand man.
- Covered with Scars: His chest is patchworked with scars received during reform school.
- Damn, It Feels Good to Be a Gangster!: Life as Bill's protege is dangerous but well-paid, as Amsterdam finds out.
- Duel to the Death: With Bill.
- No Historical Figures Were Harmed: As the foremost Irish rival of Bill the Butcher who indirectly leads to his death, allied with Boss Tweed and later going to San Francisco during the gold rush, Amsterdam borrows cues from "Old Smoke" John Morrissey
though the real Morrissey had no personal vendetta with Bill and was a much more typical gangster. - Ooh, Me Accent's Slipping: Like most Dicaprio characters, his attempt at an accent (in this case,
Irish) ranges from bad to worse. Possibly justified in the fact that he spent 16 years in a (Protestant) American orphanage, so it's probably more suprising that he has one at all.
Bill the Butcher
William "Bill the Butcher" Cutting
Portrayed By: Daniel Day-Lewis
Dubbed By: Bernard Gabay (European French)
The topmost crime boss the Five Points, and leader of the nativist gang "the Confederation of American Natives"
- Affably Evil: He's extremely charismatic and not just for the purposes of leading armies. When he's not fighting battles, he's charming, witty and capable of genuine kindness.
- Arch-Enemy: To Priest Vallon initially and later on for his son, Amsterdam Vallon, who lives only to get revenge on Billy for his father's murder. Bill himself isn't aware of it since he doesn't recognize Amsterdam at first.
- Axe-Crazy: It's not like someone named "Bill the Butcher" is ever going to be the model of mental stability with his propensity for violence, bloodthirst and sleep deprivation caused by insomnia.
- Big Bad: For the movie, since Amsterdam's revenge against him drives the plot.
- Blade Enthusiast: He uses many butcher's knives, befitting his profession. He's adept at throwing them, and when fighting hand-to-hand he prefers Dual Wielding a long knife and a monstrous cleaver.
- Blood Knight: Bill revels in combat, especially the kind involving knives and cleavers and other sharp blades in general.
- Book Dumb: He's extremely intelligent and articulate but is implied to be at least semi-illiterate, struggling to even read a pamphlet.
- Composite Character: His general character (appearance, personality, profession, role as xenophobic mobster, and even his last words) from William "Bill The Butcher" Poole, but his role as the undisputed leader of the Five Points and enforcer to Boss Tweed and the Tammany Hall machine comes from "Captain" Isaiah Rynders.
- Cruel Mercy: He was subjected to this by Priest Vallon before the movie's events when he beat him in combat, but Vallon opted to spare Bill so that he would live in shame instead. This backfired since not only did it made Cutting worse (to the point he he cut out his own eye) but he made his payback against Vallon at the start of the movie.
- The Dreaded: Everyone is terrified of Bill and with good reason, a fact he is very aware of and which he attributes as the reason he's lasted as long as he has.
- Eye for an Eye: His motto in life, as shown during his speech to Amsterdam.
- Hypocrite: A running point is that despite Bill's talk of ritual combat and honor he's very underhanded. Even in the opening scene, Bill murders Vallon (the only man he claims to respect, mind you) by attacking him from behind with a human shield and a distraction. He later also kills Monk by literally stabbing him in the back in what was a neutral ground up to that point. Even during his brief bout with Amsterdam he mostly attacks him with hit-and-run tactics.
- Frontline General: Bill is always the first man to charge into the battlefield.
- Politically Incorrect Villain: A virulently racist and anti-Irish and anti-Catholic gangster. For good measure, he also believes that the Irish want to subject America to the Vatican's influence. This "Catholics are a fifth column" attitude was very prevalent, with many Americans really believing that Catholics — immigrant or native-born — were a threat to their civil and religious liberties and traditional values. With this in mind, Billy wouldn't be considered "politically incorrect" for the time period.
- Prefers Raw Meat: The steak he prepares for himself as a meal is just lightly seared on each side, all but raw in the middle.
- Real Men Eat Meat: His idea of a good meal is to throw a steak in the pan just long enough to give each side a light sear while leaving the inside all but raw, then eating it straight from a butcher block with one of his fighting knives and a carving fork.
- Red Right Hand: He has a glass eye.
- Villain Respect: He respected Priest Vallon, recognizing that he was an honorable man and a brave fighter and that the only real difference separating them was faith, Vallon having been a Catholic and Bill a Protestant.
- Worthy Opponent: He sincerely respected Priest Vallon and even demanded his body not be mutilated for trophies as was standard.
Jenny
Jenny Everdeane
Portrayed By: Cameron Diaz
A thief and conwoman and protegè of Bill the Butcher, as well as Amsterdam's love interest.
- Con Woman: She dresses as a maid in order to rob rich people.
- Earn Your Happy Ending: She survives to the end of the movie, and she and Amsterdam leave for San Francisco after the Draft Riots.
- Silk Hiding Steel: Chances are if you meet her, she'll "accidentally" bump into you and leave you in "the grace and favor of the lord'' and with a picked pocket and that will be the end of it. If you hunt her down and demand your valuables back, be prepared to receive a swift kick to your other valuables and a knife ready to fend you off.
- Slap-Slap-Kiss: How she and Amsterdam end up making love.
Boss Tweed
William "Boss" Tweed
Portrayed By: Jim Broadbent
The corrupt leader of Tammany Hall, a powerful political organization and local political machine of the Democratic Party
- Adaptational Wimp: The real Bill Tweed was in a fire company in his youth, when they were essentially street gangs themselves, and became known for his axe-wielding violence. He was also two years younger than the real Bill the Butcher. Chances are good that he would not have been intimidated by the Butcher's threats.
- Beard of Evil: A nice pointy one.
- Corrupt Politician: One of the dirtiest. His real life counterpart, believe it or not, was even dirtier.
- Faux Affably Evil: He is very welcoming and generous towards immigrants, although generally because each one represents a potential vote for him. In his own self-serving way towards the end of the film, he even laments about all the "dead" votes he has lost because of the riots.
- Historical Domain Character
- Historical Villain Downgrade: As mentioned above, the movie actually tones down the real Tweed's corruption.
- Politically Correct Villain: For the below-mentioned reasons.
- Pragmatic Villainy: Treat the immigrants well, and they're more likely to vote for you.
Happy Jack
"Happy" Jack Mulraney
Portrayed By: John C. Reilly
A former member of the Dead Rabbits turned police officer.
- Asshole Victim: When Amsterdam strangles him in a church and hangs his body from a lamp-post, no-one feels sorry for him.
- Dead Guy on Display: His fate after been strangled to death by Amsterdam, Boss Tweed is unnerved by it
- Dirty Cop: And former gangster. Bill doesn't buy his Blatant Lies about being paid to uphold the law.
- Faux Affably Evil: If reminiscing on old times when Amsterdam viewed him as an Honorary Uncle in his childhood while following Amsterdam through a church intent on murdering him counts.
- Officer O'Hara: An Irish immigrant and a corrupt police officer.
Johnny
Johnny Sirocco
Portrayed By: Henry Thomas
A thief and childhood friend of Amsterdam's.
- Dirty Coward: Mixed with Honor Before Reason, oddly enough. He betrays Amsterdam because he's sore about being The Unfavorite to Bill and the loser to Jenny's affections. His guilty conscience then propels him to confess his role to Amsterdam and help him escape, then he tries to switch sides back to Bill to save his own skin after he's caught.
- Impaled with Extreme Prejudice: Impaled on a fence by Bill and his men. Amsterdam has to put him out of his misery.
- Oh, Crap!: His face when McGloin catches him and brings him back to Bill.
- The Resenter: The reason Johnny gives up Amsterdam to Bill - he's none too pleased at the success of his childhood friend becoming Bill's right hand and more importantly, gaining Jenny's favor.
- Rewarded as a Traitor Deserves: Bill kills him for his lack of character and loyalty (to both him and Amsterdam).
Priest Vallon
"Priest" Vallon
Portrayed By: Liam Neeson
The leader of the Dead Rabbits, a gang of Irish migrants and father of Amsterdam.
- Badass Preacher: He invokes this, despite not being an actual priest or clergyman.
- Dead Star Walking: Played by Liam Neeson, and he dies ten minutes in.
- Good Scars, Evil Scars: He cuts himself with a razor right before the battle he dies in, and he's certainly a noble figure.
- Irish Priest: Not an actual priest, but he dresses like one, and happens to be a religious Irishman.
- Large and in Charge: He's the leader of the Irish immigrants and stands an imposing 6'4, edging out even Bill in height.
- Real Men Love Jesus: Devout Catholic and leader of an immigrant gang.
- We Hardly Knew Ye: He dies very early into the film so we never really get to know him well. He was a devoutly religious Irish immigrant to the U.S., he had a son and he wasn’t afraid of a fight, but that’s about all we learn.
Monk
Walter "Monk" McGinn
Portrayed By: Brendan Gleeson
An Irish migrant holding loyalty to no gang later turned barber.
- The Atoner: Monk sees himself as this. He carves a notch into his shillelagh with every kill he commits. Everyone assumes he does this as a boast, but he states that it's to remind him of what he will owe to God when he dies. Poetically, Bill carves one last notch into Monk's club to represent Monk himself before beating him to death with it.
- Carry a Big Stick: He fights with a shillelagh, an old Irish club. It's also what Bill uses to kill him.
- Fighting Irish: Irish mercenary. Enough said.
- Hoist by His Own Petard: Bill beats his head to a pulp with his own shillelagh.
- Knight in Sour Armor: Despite being perhaps the most cynical character in a deeply cynical film, Monk's desire for justice is genuine and he truly wants to make the city better, even if only as an act of atonement.
McGloin
McGloin
Portrayed By: Gary Lewis
A member of the Dead Rabbits that joins Bill.
- Bald of Evil: A racist gangster that joins the very organization that attacks Irish immigrants
- Boomerang Bigot: Initially part of Priest Vallon's Irish Catholic gang, he joins the Natives after Priest's death and takes part in the harassment of Irish migrants, as well as openly and vocally despising Amsterdam, a fellow Irish Catholic, despite remaining a Catholic himself.
- Butt-Monkey: Despite holding the important position of Bill's right hand man, McGloin is not treated with much respect and is often ridiculed by his fellow natives.
- Even Evil Has Standards: Does not agree with Amsterdam and his friends selling dead bodies for money. McGloin, due to his Catholic beliefs, staunchly agrees that a dead body should not be interfered with.
- Jerkass: He is even more unpleasant than Bill.
- Politically Incorrect Villain: The most racist and most vocal out of Bill's gang, McGloin reacts angrily whenever he sees a black person and is sure to immediately racially abuse said person on sight.
- The Quisling: Following Priest Vallon's death, he joins Bill's xenophobic "Confederation of American Natives" despite being Irish and Catholic.
Jimmy Spoils
Jimmy Spoils
Portrayed By: Lawrence Gilliard Jr.
A thief and friend of Amsterdam and Johnny.
- Black Dude Dies First: Inverted - he's one of the last characters to die, within the last 15 minutes of the film.
- Token Minority: The only black member of the Dead Rabbits. Even then, he's not allowed to join them in the final battle due to racism from within the gang.
Maggie
Hell-Cat Maggie
Portrayed By: Cara Seymour
A member of the Dead Rabbits turned failed liquor store owner.
- The Alcoholic: Opened up her own grog shop, but drank all her own liquor and went out of business. The first shot we see of her after the intro is her ordering a drink.
- Historical Domain Character: Based off a mix of the real Maggie and two other female gangsters of the time. Frighteningly enough, her depiction is probably the closest to the real deal, sharp teeth and fingernails and allnote .
Barnum
P. T. Barnum
Portrayed By: Roger Ashton-Griffiths
The businessman and showman and owner of a "Museum of Wonders"
- Historical Domain Character: Like Boss Tweed, Barnum is a historical character.
Schermerhorn
John F. Schermerhorn
Portrayed By: David Hemmings
The patriarch of one of the wealthiest families in New York
- Fearless Fool: When the Draft Riots come to his home, he sends the women upstairs and tries to hold off the mob with just two pistols. While brave, it is highly unlikely that ended well for him.
- Historical Domain Character: Based on a real historical figure who was one of antebellum New York's leading social reformers. Schermerhorn, however, died in 1851 and certainly was not murdered in the Draft Riots.
- Horrible Judge of Character: Along with Sheltered Aristocrat. Greeley warns him that riots are coming, and he dismisses it immediately. Guess what happens the next day. He also seems to take Bill's "respectable citizen" act at face value when the two meet early in the film.
