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[[folder:Jack]]
!!Jack Young
->'''Portrayed By:''' Nick Amandos
The bartender at the Bella Union.
----
* NiceGuy: Despite working in such a den of villains, he seems like a genuinely friendly person and loans Joanie quite a bit of money when she's desperate.
[[/folder]]
!!Jack Young
->'''Portrayed By:''' Nick Amandos
The bartender at the Bella Union.
----
* NiceGuy: Despite working in such a den of villains, he seems like a genuinely friendly person and loans Joanie quite a bit of money when she's desperate.
[[/folder]]
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Changed line(s) 25,27 (click to see context) from:
-->'''Swearengen:''' Sometimes I wish we could just hit 'em over the head, rob 'em, and throw their bodies in the creek.
-->'''Cy:''' But that would be wrong.
* TheCharacterDiedWithHim: [[spoiler: Implied to have been his fate during the TimeSkip between the end of series and the movie; Cy is nowhere to be seen and Joanie mentions he left the Bella Union to her. This is, of course, a result of Powers Boothe's passing in 2017.]]
-->'''Cy:''' But that would be wrong.
* TheCharacterDiedWithHim: [[spoiler: Implied to have been his fate during the TimeSkip between the end of series and the movie; Cy is nowhere to be seen and Joanie mentions he left the Bella Union to her. This is, of course, a result of Powers Boothe's passing in 2017.]]
to:
-->'''Swearengen:''' Sometimes I wish we could just hit 'em over the head, rob 'em, and throw their bodies in the creek. \n-->'''Cy:''' \\
'''Cy:''' But that would be wrong.
* TheCharacterDiedWithHim:[[spoiler: Implied [[spoiler:Implied to have been his fate during the TimeSkip between the end of series and the movie; Cy is nowhere to be seen and Joanie mentions he left the Bella Union to her. This is, of course, a result of Powers Boothe's passing in 2017.]]
'''Cy:''' But that would be wrong.
* TheCharacterDiedWithHim:
Changed line(s) 77,78 (click to see context) from:
-->'''Al:'''You do not want to be a dirt-worshipping heathen from this fucking point forward. (to Joanie) Pardon my French.
-->'''Joanie:''' Oh, I speak French.
-->'''Joanie:''' Oh, I speak French.
to:
-->'''Al:'''You do not want to be a dirt-worshipping heathen from this fucking point forward. (to Joanie) Pardon my French. \n-->'''Joanie:''' \\
'''Joanie:''' Oh, I speakFrench. French.
'''Joanie:''' Oh, I speak
Changed line(s) 119,120 (click to see context) from:
->'''Portrayed By:''' Creator/LarryCedar
to:
->'''Portrayed By:''' Creator/LarryCedar
Larry Cedar
Changed line(s) 125 (click to see context) from:
* ChronicBackstabbingDisorder: His loyalty tends to swing around from person to person depending on what the quickest route to his next fit is, but he finally settles on being loyal to Cy Tolliver: the one person he shouldn’t have.
to:
* ChronicBackstabbingDisorder: His loyalty tends to swing around from person to person depending on what the quickest route to his next fit is, but he finally settles on being loyal to Cy Tolliver: the one person he shouldn’t shouldn't have.
Changed line(s) 133 (click to see context) from:
* TooDumbToLive: He basically screams to be killed off during the first episode he is given prominence, "Mr Wu", most notably in the baths scene. Al spares him and kills his pal Jimmy Irons instead only because killing Leon would put him at war with Cy.
to:
* TooDumbToLive: He basically screams to be killed off during the first episode he is given prominence, "Mr "Mr. Wu", most notably in the baths scene. Al spares him and kills his pal Jimmy Irons instead only because killing Leon would put him at war with Cy.
Changed line(s) 140,141 (click to see context) from:
->'''Portrayed By:''' Creator/RickyJay
to:
->'''Portrayed By:''' Creator/RickyJay
Ricky Jay
Changed line(s) 160 (click to see context) from:
->'''Portrayed By:''' Creator/ParisseBoothe
to:
->'''Portrayed By:''' Creator/ParisseBootheParisse Boothe
Changed line(s) 165,166 (click to see context) from:
->'''Portrayed By:''' Creator/MeghanGlennon
to:
->'''Portrayed By:''' Creator/MeghanGlennon
Meghan Glennon
Changed line(s) 172,173 (click to see context) from:
->'''Portrayed By:''' Creator/SarahPachelli
to:
->'''Portrayed By:''' Creator/SarahPachelli
Sarah Pachelli
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->'''Portrayed By:''' Creator/EricaSwanson
to:
->'''Portrayed By:''' Creator/EricaSwanson
Erica Swanson
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[[/folder]]
to:
----
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Nice Hat is now dewicked
Deleted line(s) 83 (click to see context) :
* NiceHat: Joanie typically wears a top hat with a long veil flowing behind.
Deleted line(s) 113 (click to see context) :
* NiceHat: Con is distinguished by his tall, garish hat.
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Badass Mustache and Badass Beard are being merged into Manly Facial Hair. Examples that don't fit or are zero-context are removed. Having facial hair is not enough to qualify. To qualify for Manly Facial Hair, the facial hair must be associated with masculinity/manliness in some way. Please read the trope description before readding to make sure the example qualifies.
Deleted line(s) 21 (click to see context) :
* BadassMoustache: It's Powers Boothe, so of course he has this.
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Deleted line(s) 115 (click to see context) :
* ThoseTwoBadGuys: After falling under the employ of Cy Tolliver, he forges a working relationship with dope addict Leon and from there on the two are rarely seen apart.
Deleted line(s) 137 (click to see context) :
* ThoseTwoBadGuys: First with Jimmy Irons, later with Con Stapleton.
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!The Bella Union
[[foldercontrol]]
!!!Ownership
[[folder:Cy]]
!!Cyrus "Cy" Tolliver
[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/tolliver_cyrus_1.jpg]]
[[caption-width-right:300:''"[[FauxAffablyEvil You can help your delicate sensibilities by turning the fuck away.]]"'']]
->'''Played By:''' Creator/PowersBoothe
-->''"How about a nap, a bath and sex with a unfamiliar woman?"''
Al Swearengen's worst nightmare came true when Cy Tolliver brought his own den of gambling and whoring to Deadwood from Chicago. Tolliver's Bella Union is a high class joint, offering more refined and well-kept prostitutes along with sophisticated gaming, including craps.
A former riverboat gambler, Tolliver has been around, and he sees the unlimited earning potential the lawless town of Deadwood offers. Having done his homework and placed his own spies in town, Tolliver quickly establishes that he's not afraid of going head-to-head with Al, and he is just as calculating and wily as his competition.
----
* AmbitionIsEvil: Cy has great plans for his future, and his ambition results in him making more and more monstrous (and sometimes ill-advised) decisions that even Al would balk at.
* AxCrazy: His nifty dress sense and quick smile are a thin veneer for what he truly is: a vicious jackal who kills before thinking.
* BadassMoustache: It's Powers Boothe, so of course he has this.
* BadBoss: Cy bullies, threatens and outright murders his employees from time to time.
* BigBadWannabe: He's essentially a darker version of E.B. Farnum - a SmugSnake who desperately wants to be a major player in the town's politics, but whose poorly executed schemes and toxic personality leave him at the mercy of bigger predators like [[BigBad George Hearst]].
* BitchInSheepsClothing: He can pretend to be civil...for all of five minutes.
* ButThatWouldBeWrong: Says it word-for-word in one of his snarky moments.
-->'''Swearengen:''' Sometimes I wish we could just hit 'em over the head, rob 'em, and throw their bodies in the creek.
-->'''Cy:''' But that would be wrong.
* TheCharacterDiedWithHim: [[spoiler: Implied to have been his fate during the TimeSkip between the end of series and the movie; Cy is nowhere to be seen and Joanie mentions he left the Bella Union to her. This is, of course, a result of Powers Boothe's passing in 2017.]]
* TheDandy: He is well-dressed and groomed, in contrast to pretty much everyone else in the camp.
* DeadpanSnarker: He has some bitterly dry lines.
-->''"[during Swearengen's and Bullock's fight] Awful possibility in these matters is both men sustaining mortal injury... [After the fight] But I'm rarely that fucking lucky."''
-->''"That group and employer bullshit really quickens me with fuckin' trust."''
-->''"Tell Al as we didn't wake to the apocalypse, I suppose all we need fear is their Winchesters."''
* DemotedToDragon: After he sides with Hearst.
* DisproportionateRetribution: So, you want to steal in his saloon (but not even from him)? You better think it again. He will administer such a terrible beating on you that death will be a mercy.
* EvenEvilHasStandards: [[spoiler:He's disgusted by Wolcott's penchant for murdering prostitutes, though not to the extent that he won't help out with covering it up to gain leverage. He also can do nothing but insult Hearst when he first sees that Hearst has ordered the death of Ellsworth.]]
* EvilCounterpart: To Al. Notable, considering that Al is already evil, but affable.
* EvilMentor: To Joanie.
* EvilerThanThou: Cy's character is essentially a version of Al that lacks the flickers of humanity that Al demonstrates.
* FauxAffablyEvil:
** Cy can be genial and even charming, but he has trouble keeping it up. His sharp dress sense does a better job of hiding what a savage animal he is.
** He and Al act as a good case study for the differences between FauxAffablyEvil and AffablyEvil, respectively.
* {{Foil}}: To Al. Both are ruthless saloon and brothel owners, but there are marked differences in the two.
** Al has standards and good intent, not to mention he does seem to like a select few people. Cy sees people only as pawns to be used.
** Al keeps himself surrounded by henchmen who are at least basically competent, and loyal to him. Cy employs a series of {{Yes M|an}}en, alienating anyone who could truly benefit him.
** Al has Trixie, his favored whore, much like Cy has Joanie. However, Al not only has a physical relationship with Trixie (which Cy does not have with Joanie, or at least has no longer) but at his core he does care for her. Al is willing to let Trixie go and make a better life for herself despite his talk; Cy makes empty promises about letting Joanie go as well, but he has absolutely no intention of letting her have anything but a 'looser rein'.
* HairTriggerTemper: He has trouble keeping his fiery temper in check, and can blow up at people sometimes for no reason.
* HumiliationConga: Starting with Wolcott's arrival in camp, Cy is forced to endure mounting humiliations as his standing in Deadwood weakens.
-->'''Wolcott:''' You're a desperate man, aren't you, Tolliver? Desperate. You feel your position weakening.
* IncompatibleOrientation: With Joanie, who he seems to love. She's a lesbian.
* JerkWithAHeartOfJerk: Every time Cy shows even the slightest hint of an affable nature or genuine good intent, he subverts it by letting his rage overtake him or just becoming a sadistic beast on a turn.
* PetTheDog: Don't expect even the ''slightest'' bit of decency from Cy, unless your name is [[MoralityPet Joanie.]] He rescued her from her own incestuous, abusive father (although this might just be because Cy [[PragmaticVillainy saw value in her]]) In the movie, it's even mentioned that he left the Bella Union to her in his will.
** Even ''Cy'' is infuriated when Hearst has [[spoiler:Ellsworth]] killed.
* PoliticallyIncorrectVillain: He stands out even though the show averts PoliticallyCorrectHistory as much as possible. Ironically, he is the only one that claims to [[EqualOpportunityEvil respect Chinese customs]]... though that was most likely because it meant more money for him. Cy is also a misogynist to the core, despite his feelings for Joanie.
-->''"Don't believe there's no good women 'till you've seen one with maggots in her eyes."''
* SanitySlippage: [[spoiler:After being stabbed, his mental health begins to fail and he becomes even more violently unpredictable.]]
* SmugSnake: Fancies himself a MagnificentBastard. However, while he doesn't lack for brains or ambition, Cy tends to overestimate himself. His skills at long-term decision making are practically neutered by his unhinged mental state and his AxeCrazy BadBoss tendencies only serve to drive away any potential allies, forcing him to rely on [[SurroundedByIdiots clumsy lickspittles and inept junkies who couldn't think their way out of a box]].
* SurroundedByIdiots: One of the key differences between Cy and Al is that Al has people he can depend on...the loyal Johnny Burns, the powerful Dan Dority, the cunning Silas Adams. Cy, meanwhile, has to depend on Leon and Con Stapleton, a pair of easily distracted idiots. Cy alienates everyone under his employ who's even halfway competent like Joanie, Andy or Eddie Sawyer.
* VillainousBreakdown: Cy progressively goes through one in Season 3 as a result of Hearst's machinations and the physical after-effects of [[spoiler:his stabbing]], culminating in a massive explosion of impotent rage in the final episode.
* YouHaveFailedMe: Has a tendency to do this to his employees.
[[/folder]]
[[folder:Joanie]]
!!Joanie Stubbs
[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/stubbs_joan_1108.jpg]]
[[caption-width-right:350:''"I wish once I could care for those little ones. Just once instead of doin' what I did."'']]
->'''Played By:''' Creator/KimDickens
-->'''Jack Langrishe:''' The blessed Miss Stubbs, whose bust is so very prominent in the mind's pantheon of the camp.
Joanie Stubbs is Cy Tolliver's former madam at the Bella Union. Joanie, unlike Trixie, acts only as the hostess, and not as a prostitute herself. Although she is a lesbian, Stubbs has a long relationship with Cy and is one of the few people Cy cares for, though his increasingly unpredictable and violent behavior sours their friendship. Often depressed and self-loathing, she was apparently bought by Cy from her own father, who had abused and pimped her and her younger sisters as prostitutes. Joanie also reveals that her father used her to coerce her sisters to sleep with him—to "see to his needs since mama was gone." As a result, the emotionally scarred Joanie is weighed down by guilt.
----
* AbusiveParents: Her father raped her and her sisters, before selling her into slavery at the age of 14.
* BrokenBird: Joanie's life has consisted of being used and abused by a succession of evil men, and at the start of the series she's still under Cy Tolliver's control. While much of the time, Joanie is a charming and pleasant woman with a quick wit, underneath she's a vulnerable and traumatized person.
* DeadpanSnarker: She has a sharp tongue.
-->'''Al:'''You do not want to be a dirt-worshipping heathen from this fucking point forward. (to Joanie) Pardon my French.
-->'''Joanie:''' Oh, I speak French.
* DespairEventHorizon: In Season 1, when Cy forces her to shoot the thief that stole from her. Again in Season 2, when [[spoiler: Francis Wolcott kills her business partner and two women more in her brothel.]]
* GorgeousPeriodDress: Joanie is one of the more fashionable character, usually dressed in a beautiful dress complete with a nifty hat.
* HighClassCallGirl: She's a much higher class of prostitute than Al's more earthy employees like Trixie and Dolly. Joanie is well-dressed, charming and seductive while Al's prostitutes tend to be all-business.
* HookerWithAHeartOfGold: She's a prostitute and one of the most kind-hearted characters in the show.
* NiceHat: Joanie typically wears a top hat with a long veil flowing behind.
* LipstickLesbian: She's easily the most attractive of the female main cast (with the possible exception of Alma) and it isn't hard to see why men fall for her so easily. Unfortunately for them (and fortunately for women) she isn't attracted to men.
* MadeASlave: After her mother died, her father prostituted her and later sold her to Cy.
* MissKitty: Within the Bella Union. She later tries to strike out on her own with OldFriend Maddie, [[spoiler:but things go terribly wrong.]]
* MoralityPet: To Cy, although he's often cruel [[KickTheMoralityPet even to her.]]
* NumberTwo: To Cy Tolliver, during Season 1. After that she strikes out on her own.
* OfficialCouple: [[spoiler: With Jane, eventually.]]
* PlatonicLifePartners: Becomes this with Charlie.
* RapeAsBackstory: Her father molested and pimped her out as a young child.
* TookALevelInBadass: When she [[spoiler:beats Francis Wolcott over the head with a bottle.]]
[[/folder]]
!!!Staff
[[folder:Stapleton]]
!!Con Stapleton
[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/stapleton_con.jpg]]
->'''Portrayed By:''' Creator/PeterJason
The dim-witted card dealer at the No. 10 saloon. He can be easily distinguished by his large, bright-colored and ill-fitting hat, which he is never seen without. Stapleton is briefly installed as sheriff when the Number 10's owner, Tom Nuttall, began to fear that the camp was "leaving him behind" and asked Al Swearengen to set up his employee in a position of power.
However, Stapleton quickly let himself be bribed by Tolliver to stir up anti-Chinese sentiment. After murdering a Chinese resident of the camp without justification, he is stripped of his badge by an enraged Bullock. While Nuttall renounced him following the incident, Stapleton has remained in Tolliver's employ, often working with Leon, doing odd jobs such as security at the Bella Union and trashing Merrick's printing press.
----
* AgeLift: The real Con Stapleton was in his twenties when he lived in Deadwood; here, he's played by the much older Peter Jason.
* BumblingSidekick: Along with Leon, he serves as a highly incompetent sidekick to the ruthless Cy Tolliver. Stapleton can't do much right, although he is marginally more competent and affable than Leon.
* DirtyCop: Con is responsible for originating the role of sheriff within Deadwood (with the help of Tom Nuttall and the reluctant aid of Al Swearengen), but he only ever wanted the job to enjoy the fruits of his own corruption. As a result, he doesn't last long.
* FanDisservice: Seriously, who though that giving Con ''two'' 'sexy' scenes in Season 3 was a good idea?
* HeelFaithTurn: [[spoiler:In the ten-year TimeSkip between the show and movie, Con has become a Reverend, and it's he who officiates Sol and Trixie's wedding.]]
* HistoricalVillainUpgrade: Con is bumbling, incompetent, overconfident and foolish. This is a far cry from historical reports of the real Con Stapleton, who served as Deadwood's city marshal for about a year and seems to have been quite popular. He also was capable of some badass [[http://www.legendsofamerica.com/sd-constapleton.html stunts]] well far from the pathetic gimmicks of the TV character.
* MinionWithAnFInEvil: He's a self-serving bumbler, but at worst he helps stoke up resentment within the camp. He's hardly a hired killer and there isn't malice behind his actions so much as selfishness.
* NiceHat: Con is distinguished by his tall, garish hat.
* ThoseTwoBadGuys: After falling under the employ of Cy Tolliver, he forges a working relationship with dope addict Leon and from there on the two are rarely seen apart.
* TookALevelInKindness: [[spoiler:Following the TimeSkip, he's become Deadwood's reverend, and has changed his attitude to suit. He's as incompetent as ever, but he's a good deal nicer and more liked. He even tries (clumsily, but sincerely) to make sure Sol's "Jewishness" is accomodated at his wedding. Perhaps Leon's death served as a warning to change his ways.]]
* YesMan: To Cy, who can't stomach outside opinions from his peons.
[[/folder]]
[[folder:Leon]]
!!Leon
[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/leon2.jpg]]
->'''Portrayed By:''' Creator/LarryCedar
Leon, Cy Tolliver's general informant and lackey, is addicted to opium. Formerly employed as a double agent to give Swearengen false information, he and the dope fiend Jimmy Irons robbed and murdered Mr. Wu's opium courier, leading to Jimmy being fed to Wu's pigs. Leon worked to incite anti-Chinese sentiment in the camp following this event, though more out of fear of Cy than anything else, and now serves as Tolliver's eyes around town.
----
* BumblingSidekick: Leon is deeply incompetent, and can at best be cautiously relied on to fulfill menial tasks. Mostly,though, he impedes whoever he works for.
* ButtMonkey: Not much goes right for him, but it's pretty much entirely his own doing.
* ChronicBackstabbingDisorder: His loyalty tends to swing around from person to person depending on what the quickest route to his next fit is, but he finally settles on being loyal to Cy Tolliver: the one person he shouldn’t have.
* FirstNameBasis: With everyone. His last name is unknown.
* HarmlessVillain: Leon's too much of a gutless wreck to be any kind of real threat by himself.
* {{Jerkass}}: Leon is simply unpleasant: a loud-mouthed, whining, racist junkie who only cares about himself and his next fix.
* PoliticallyIncorrectVillain: In this case, a drug addict that ''really'' hates Chinamen. Granted, he's been charged to spread anti-Chinese sentiment, but damn if he isn't vitriolic in his performance.
* ProfessionalButtKisser: Since he has no actual uses, he resorts to being an ass-kissing toady. He even tries to compliment Cy as he bleeds to death from a stab wound ''Cy'' inflicted!
-->'''Cy:''' If those were your last words, tell the Lord you died stupid.
* TheStoner: He's an opium addict, motivated entirely by where his next fix is coming from.
* ThoseTwoBadGuys: First with Jimmy Irons, later with Con Stapleton.
* TooDumbToLive: He basically screams to be killed off during the first episode he is given prominence, "Mr Wu", most notably in the baths scene. Al spares him and kills his pal Jimmy Irons instead only because killing Leon would put him at war with Cy.
* YesMan: To Cy.
[[/folder]]
[[folder:Eddie]]
!!Eddie Sawyer
[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/TropeEddieSawyer_9007.jpg]][[caption-width-right:350:''"Did that blood stain get you the special rate?"'']]
->'''Portrayed By:''' Creator/RickyJay
A card shark at Cy Tolliver's Bella Union saloon, Sawyer had worked with Tolliver for 17 years and was one of Cy's most reliable hands.
----
* AffablyEvil: Eddie is a con-man who takes advantage of others and has worked alongside proud-and-loud AxCrazy psychopath Cy Tolliver for seventeen years, but he's a genuinely charming man with an endearing wit. Nor is he sadistic or cruel, showing distaste for Cy's violent tendencies and ultimately leaves his employ, but not before stealing from right under Cy's nose and gifting money to Joanie so she can get out from under him.
* AmbiguouslyGay: He never really shows interest in the beautiful prostitutes in the Bella Union. After Cy kills the Anderson siblings and Eddie is upset about the brutality of it, Cy accuses him of harboring affection for young boys like Miles. Eddie says "I never did that," but considering that Cy could have easily made the same accusation about Flora, and Eddie never protests that he's not attracted to males in general, it's possible Cy knows Eddie is gay.
* CreatorCameo: Ricky Jay is a writer as well as an actor (also a magician, which is cool) and he's written episodes of Deadwood.
* DeadpanSnarker: As per usual for a Ricky Jay character; Eddie has a sharp wit that's on-display in every scene.
* TheDogBitesBack: Cy and Eddie get along pretty well, but after Cy suddenly becomes angry and humiliates him publicly, he resolves to steal from Cy and get the hell out of dodge.
* HyperCompetentSidekick: Eddie is a highly intelligent man who gives Cy valuable advice. When he leaves, it's the beginning of Cy's downfall.
* MinionWithAnFInEvil: He's a minion of Cy, but he's pleasant, witty and doesn't really do anything evil aside from associating with Cy.
* MistreatmentInducedBetrayal: Eddie is a pretty loyal NumberTwo to Cy Tolliver, but Cy's unpredictable temper and mistreatment of both Eddie and Joanie lead to Eddie abandoning him.
* NumberTwo: To Cy, initially. Eventually Cy drives him away with his too-frequent displays of violence and a particular moment of public humiliation.
* PutOnABus: At the end of Season 1, Eddie steals from Cy and flees Deadwood, never to be seen again.
[[/folder]]
!!!Bella Union Sex Workers
[[folder:Tess]]
!!Tess
->'''Portrayed By:''' Creator/ParisseBoothe
[[/folder]]
[[folder:Lila]]
!!Lila
->'''Portrayed By:''' Creator/MeghanGlennon
* TheStoner: She's addicted to opium.
[[/folder]]
[[folder:Janine]]
!!Janine
->'''Portrayed By:''' Creator/SarahPachelli
* TheChewtoy: She becomes one for Cy, who alternates between speechifying to her and abusing her.
[[/folder]]
[[folder:Doris]]
!!Doris
->'''Portrayed By:''' Creator/EricaSwanson
* TheMole: Cy employs her to spy on Joanie and Maddie's new enterprise while working for them. Joanie sees through her right away, to the point where it almost seems like Cy wanted her to know.
* SlashedThroat: At Wolcott's hands.
[[/folder]]
[[foldercontrol]]
!!!Ownership
[[folder:Cy]]
!!Cyrus "Cy" Tolliver
[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/tolliver_cyrus_1.jpg]]
[[caption-width-right:300:''"[[FauxAffablyEvil You can help your delicate sensibilities by turning the fuck away.]]"'']]
->'''Played By:''' Creator/PowersBoothe
-->''"How about a nap, a bath and sex with a unfamiliar woman?"''
Al Swearengen's worst nightmare came true when Cy Tolliver brought his own den of gambling and whoring to Deadwood from Chicago. Tolliver's Bella Union is a high class joint, offering more refined and well-kept prostitutes along with sophisticated gaming, including craps.
A former riverboat gambler, Tolliver has been around, and he sees the unlimited earning potential the lawless town of Deadwood offers. Having done his homework and placed his own spies in town, Tolliver quickly establishes that he's not afraid of going head-to-head with Al, and he is just as calculating and wily as his competition.
----
* AmbitionIsEvil: Cy has great plans for his future, and his ambition results in him making more and more monstrous (and sometimes ill-advised) decisions that even Al would balk at.
* AxCrazy: His nifty dress sense and quick smile are a thin veneer for what he truly is: a vicious jackal who kills before thinking.
* BadassMoustache: It's Powers Boothe, so of course he has this.
* BadBoss: Cy bullies, threatens and outright murders his employees from time to time.
* BigBadWannabe: He's essentially a darker version of E.B. Farnum - a SmugSnake who desperately wants to be a major player in the town's politics, but whose poorly executed schemes and toxic personality leave him at the mercy of bigger predators like [[BigBad George Hearst]].
* BitchInSheepsClothing: He can pretend to be civil...for all of five minutes.
* ButThatWouldBeWrong: Says it word-for-word in one of his snarky moments.
-->'''Swearengen:''' Sometimes I wish we could just hit 'em over the head, rob 'em, and throw their bodies in the creek.
-->'''Cy:''' But that would be wrong.
* TheCharacterDiedWithHim: [[spoiler: Implied to have been his fate during the TimeSkip between the end of series and the movie; Cy is nowhere to be seen and Joanie mentions he left the Bella Union to her. This is, of course, a result of Powers Boothe's passing in 2017.]]
* TheDandy: He is well-dressed and groomed, in contrast to pretty much everyone else in the camp.
* DeadpanSnarker: He has some bitterly dry lines.
-->''"[during Swearengen's and Bullock's fight] Awful possibility in these matters is both men sustaining mortal injury... [After the fight] But I'm rarely that fucking lucky."''
-->''"That group and employer bullshit really quickens me with fuckin' trust."''
-->''"Tell Al as we didn't wake to the apocalypse, I suppose all we need fear is their Winchesters."''
* DemotedToDragon: After he sides with Hearst.
* DisproportionateRetribution: So, you want to steal in his saloon (but not even from him)? You better think it again. He will administer such a terrible beating on you that death will be a mercy.
* EvenEvilHasStandards: [[spoiler:He's disgusted by Wolcott's penchant for murdering prostitutes, though not to the extent that he won't help out with covering it up to gain leverage. He also can do nothing but insult Hearst when he first sees that Hearst has ordered the death of Ellsworth.]]
* EvilCounterpart: To Al. Notable, considering that Al is already evil, but affable.
* EvilMentor: To Joanie.
* EvilerThanThou: Cy's character is essentially a version of Al that lacks the flickers of humanity that Al demonstrates.
* FauxAffablyEvil:
** Cy can be genial and even charming, but he has trouble keeping it up. His sharp dress sense does a better job of hiding what a savage animal he is.
** He and Al act as a good case study for the differences between FauxAffablyEvil and AffablyEvil, respectively.
* {{Foil}}: To Al. Both are ruthless saloon and brothel owners, but there are marked differences in the two.
** Al has standards and good intent, not to mention he does seem to like a select few people. Cy sees people only as pawns to be used.
** Al keeps himself surrounded by henchmen who are at least basically competent, and loyal to him. Cy employs a series of {{Yes M|an}}en, alienating anyone who could truly benefit him.
** Al has Trixie, his favored whore, much like Cy has Joanie. However, Al not only has a physical relationship with Trixie (which Cy does not have with Joanie, or at least has no longer) but at his core he does care for her. Al is willing to let Trixie go and make a better life for herself despite his talk; Cy makes empty promises about letting Joanie go as well, but he has absolutely no intention of letting her have anything but a 'looser rein'.
* HairTriggerTemper: He has trouble keeping his fiery temper in check, and can blow up at people sometimes for no reason.
* HumiliationConga: Starting with Wolcott's arrival in camp, Cy is forced to endure mounting humiliations as his standing in Deadwood weakens.
-->'''Wolcott:''' You're a desperate man, aren't you, Tolliver? Desperate. You feel your position weakening.
* IncompatibleOrientation: With Joanie, who he seems to love. She's a lesbian.
* JerkWithAHeartOfJerk: Every time Cy shows even the slightest hint of an affable nature or genuine good intent, he subverts it by letting his rage overtake him or just becoming a sadistic beast on a turn.
* PetTheDog: Don't expect even the ''slightest'' bit of decency from Cy, unless your name is [[MoralityPet Joanie.]] He rescued her from her own incestuous, abusive father (although this might just be because Cy [[PragmaticVillainy saw value in her]]) In the movie, it's even mentioned that he left the Bella Union to her in his will.
** Even ''Cy'' is infuriated when Hearst has [[spoiler:Ellsworth]] killed.
* PoliticallyIncorrectVillain: He stands out even though the show averts PoliticallyCorrectHistory as much as possible. Ironically, he is the only one that claims to [[EqualOpportunityEvil respect Chinese customs]]... though that was most likely because it meant more money for him. Cy is also a misogynist to the core, despite his feelings for Joanie.
-->''"Don't believe there's no good women 'till you've seen one with maggots in her eyes."''
* SanitySlippage: [[spoiler:After being stabbed, his mental health begins to fail and he becomes even more violently unpredictable.]]
* SmugSnake: Fancies himself a MagnificentBastard. However, while he doesn't lack for brains or ambition, Cy tends to overestimate himself. His skills at long-term decision making are practically neutered by his unhinged mental state and his AxeCrazy BadBoss tendencies only serve to drive away any potential allies, forcing him to rely on [[SurroundedByIdiots clumsy lickspittles and inept junkies who couldn't think their way out of a box]].
* SurroundedByIdiots: One of the key differences between Cy and Al is that Al has people he can depend on...the loyal Johnny Burns, the powerful Dan Dority, the cunning Silas Adams. Cy, meanwhile, has to depend on Leon and Con Stapleton, a pair of easily distracted idiots. Cy alienates everyone under his employ who's even halfway competent like Joanie, Andy or Eddie Sawyer.
* VillainousBreakdown: Cy progressively goes through one in Season 3 as a result of Hearst's machinations and the physical after-effects of [[spoiler:his stabbing]], culminating in a massive explosion of impotent rage in the final episode.
* YouHaveFailedMe: Has a tendency to do this to his employees.
[[/folder]]
[[folder:Joanie]]
!!Joanie Stubbs
[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/stubbs_joan_1108.jpg]]
[[caption-width-right:350:''"I wish once I could care for those little ones. Just once instead of doin' what I did."'']]
->'''Played By:''' Creator/KimDickens
-->'''Jack Langrishe:''' The blessed Miss Stubbs, whose bust is so very prominent in the mind's pantheon of the camp.
Joanie Stubbs is Cy Tolliver's former madam at the Bella Union. Joanie, unlike Trixie, acts only as the hostess, and not as a prostitute herself. Although she is a lesbian, Stubbs has a long relationship with Cy and is one of the few people Cy cares for, though his increasingly unpredictable and violent behavior sours their friendship. Often depressed and self-loathing, she was apparently bought by Cy from her own father, who had abused and pimped her and her younger sisters as prostitutes. Joanie also reveals that her father used her to coerce her sisters to sleep with him—to "see to his needs since mama was gone." As a result, the emotionally scarred Joanie is weighed down by guilt.
----
* AbusiveParents: Her father raped her and her sisters, before selling her into slavery at the age of 14.
* BrokenBird: Joanie's life has consisted of being used and abused by a succession of evil men, and at the start of the series she's still under Cy Tolliver's control. While much of the time, Joanie is a charming and pleasant woman with a quick wit, underneath she's a vulnerable and traumatized person.
* DeadpanSnarker: She has a sharp tongue.
-->'''Al:'''You do not want to be a dirt-worshipping heathen from this fucking point forward. (to Joanie) Pardon my French.
-->'''Joanie:''' Oh, I speak French.
* DespairEventHorizon: In Season 1, when Cy forces her to shoot the thief that stole from her. Again in Season 2, when [[spoiler: Francis Wolcott kills her business partner and two women more in her brothel.]]
* GorgeousPeriodDress: Joanie is one of the more fashionable character, usually dressed in a beautiful dress complete with a nifty hat.
* HighClassCallGirl: She's a much higher class of prostitute than Al's more earthy employees like Trixie and Dolly. Joanie is well-dressed, charming and seductive while Al's prostitutes tend to be all-business.
* HookerWithAHeartOfGold: She's a prostitute and one of the most kind-hearted characters in the show.
* NiceHat: Joanie typically wears a top hat with a long veil flowing behind.
* LipstickLesbian: She's easily the most attractive of the female main cast (with the possible exception of Alma) and it isn't hard to see why men fall for her so easily. Unfortunately for them (and fortunately for women) she isn't attracted to men.
* MadeASlave: After her mother died, her father prostituted her and later sold her to Cy.
* MissKitty: Within the Bella Union. She later tries to strike out on her own with OldFriend Maddie, [[spoiler:but things go terribly wrong.]]
* MoralityPet: To Cy, although he's often cruel [[KickTheMoralityPet even to her.]]
* NumberTwo: To Cy Tolliver, during Season 1. After that she strikes out on her own.
* OfficialCouple: [[spoiler: With Jane, eventually.]]
* PlatonicLifePartners: Becomes this with Charlie.
* RapeAsBackstory: Her father molested and pimped her out as a young child.
* TookALevelInBadass: When she [[spoiler:beats Francis Wolcott over the head with a bottle.]]
[[/folder]]
!!!Staff
[[folder:Stapleton]]
!!Con Stapleton
[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/stapleton_con.jpg]]
->'''Portrayed By:''' Creator/PeterJason
The dim-witted card dealer at the No. 10 saloon. He can be easily distinguished by his large, bright-colored and ill-fitting hat, which he is never seen without. Stapleton is briefly installed as sheriff when the Number 10's owner, Tom Nuttall, began to fear that the camp was "leaving him behind" and asked Al Swearengen to set up his employee in a position of power.
However, Stapleton quickly let himself be bribed by Tolliver to stir up anti-Chinese sentiment. After murdering a Chinese resident of the camp without justification, he is stripped of his badge by an enraged Bullock. While Nuttall renounced him following the incident, Stapleton has remained in Tolliver's employ, often working with Leon, doing odd jobs such as security at the Bella Union and trashing Merrick's printing press.
----
* AgeLift: The real Con Stapleton was in his twenties when he lived in Deadwood; here, he's played by the much older Peter Jason.
* BumblingSidekick: Along with Leon, he serves as a highly incompetent sidekick to the ruthless Cy Tolliver. Stapleton can't do much right, although he is marginally more competent and affable than Leon.
* DirtyCop: Con is responsible for originating the role of sheriff within Deadwood (with the help of Tom Nuttall and the reluctant aid of Al Swearengen), but he only ever wanted the job to enjoy the fruits of his own corruption. As a result, he doesn't last long.
* FanDisservice: Seriously, who though that giving Con ''two'' 'sexy' scenes in Season 3 was a good idea?
* HeelFaithTurn: [[spoiler:In the ten-year TimeSkip between the show and movie, Con has become a Reverend, and it's he who officiates Sol and Trixie's wedding.]]
* HistoricalVillainUpgrade: Con is bumbling, incompetent, overconfident and foolish. This is a far cry from historical reports of the real Con Stapleton, who served as Deadwood's city marshal for about a year and seems to have been quite popular. He also was capable of some badass [[http://www.legendsofamerica.com/sd-constapleton.html stunts]] well far from the pathetic gimmicks of the TV character.
* MinionWithAnFInEvil: He's a self-serving bumbler, but at worst he helps stoke up resentment within the camp. He's hardly a hired killer and there isn't malice behind his actions so much as selfishness.
* NiceHat: Con is distinguished by his tall, garish hat.
* ThoseTwoBadGuys: After falling under the employ of Cy Tolliver, he forges a working relationship with dope addict Leon and from there on the two are rarely seen apart.
* TookALevelInKindness: [[spoiler:Following the TimeSkip, he's become Deadwood's reverend, and has changed his attitude to suit. He's as incompetent as ever, but he's a good deal nicer and more liked. He even tries (clumsily, but sincerely) to make sure Sol's "Jewishness" is accomodated at his wedding. Perhaps Leon's death served as a warning to change his ways.]]
* YesMan: To Cy, who can't stomach outside opinions from his peons.
[[/folder]]
[[folder:Leon]]
!!Leon
[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/leon2.jpg]]
->'''Portrayed By:''' Creator/LarryCedar
Leon, Cy Tolliver's general informant and lackey, is addicted to opium. Formerly employed as a double agent to give Swearengen false information, he and the dope fiend Jimmy Irons robbed and murdered Mr. Wu's opium courier, leading to Jimmy being fed to Wu's pigs. Leon worked to incite anti-Chinese sentiment in the camp following this event, though more out of fear of Cy than anything else, and now serves as Tolliver's eyes around town.
----
* BumblingSidekick: Leon is deeply incompetent, and can at best be cautiously relied on to fulfill menial tasks. Mostly,though, he impedes whoever he works for.
* ButtMonkey: Not much goes right for him, but it's pretty much entirely his own doing.
* ChronicBackstabbingDisorder: His loyalty tends to swing around from person to person depending on what the quickest route to his next fit is, but he finally settles on being loyal to Cy Tolliver: the one person he shouldn’t have.
* FirstNameBasis: With everyone. His last name is unknown.
* HarmlessVillain: Leon's too much of a gutless wreck to be any kind of real threat by himself.
* {{Jerkass}}: Leon is simply unpleasant: a loud-mouthed, whining, racist junkie who only cares about himself and his next fix.
* PoliticallyIncorrectVillain: In this case, a drug addict that ''really'' hates Chinamen. Granted, he's been charged to spread anti-Chinese sentiment, but damn if he isn't vitriolic in his performance.
* ProfessionalButtKisser: Since he has no actual uses, he resorts to being an ass-kissing toady. He even tries to compliment Cy as he bleeds to death from a stab wound ''Cy'' inflicted!
-->'''Cy:''' If those were your last words, tell the Lord you died stupid.
* TheStoner: He's an opium addict, motivated entirely by where his next fix is coming from.
* ThoseTwoBadGuys: First with Jimmy Irons, later with Con Stapleton.
* TooDumbToLive: He basically screams to be killed off during the first episode he is given prominence, "Mr Wu", most notably in the baths scene. Al spares him and kills his pal Jimmy Irons instead only because killing Leon would put him at war with Cy.
* YesMan: To Cy.
[[/folder]]
[[folder:Eddie]]
!!Eddie Sawyer
[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/TropeEddieSawyer_9007.jpg]][[caption-width-right:350:''"Did that blood stain get you the special rate?"'']]
->'''Portrayed By:''' Creator/RickyJay
A card shark at Cy Tolliver's Bella Union saloon, Sawyer had worked with Tolliver for 17 years and was one of Cy's most reliable hands.
----
* AffablyEvil: Eddie is a con-man who takes advantage of others and has worked alongside proud-and-loud AxCrazy psychopath Cy Tolliver for seventeen years, but he's a genuinely charming man with an endearing wit. Nor is he sadistic or cruel, showing distaste for Cy's violent tendencies and ultimately leaves his employ, but not before stealing from right under Cy's nose and gifting money to Joanie so she can get out from under him.
* AmbiguouslyGay: He never really shows interest in the beautiful prostitutes in the Bella Union. After Cy kills the Anderson siblings and Eddie is upset about the brutality of it, Cy accuses him of harboring affection for young boys like Miles. Eddie says "I never did that," but considering that Cy could have easily made the same accusation about Flora, and Eddie never protests that he's not attracted to males in general, it's possible Cy knows Eddie is gay.
* CreatorCameo: Ricky Jay is a writer as well as an actor (also a magician, which is cool) and he's written episodes of Deadwood.
* DeadpanSnarker: As per usual for a Ricky Jay character; Eddie has a sharp wit that's on-display in every scene.
* TheDogBitesBack: Cy and Eddie get along pretty well, but after Cy suddenly becomes angry and humiliates him publicly, he resolves to steal from Cy and get the hell out of dodge.
* HyperCompetentSidekick: Eddie is a highly intelligent man who gives Cy valuable advice. When he leaves, it's the beginning of Cy's downfall.
* MinionWithAnFInEvil: He's a minion of Cy, but he's pleasant, witty and doesn't really do anything evil aside from associating with Cy.
* MistreatmentInducedBetrayal: Eddie is a pretty loyal NumberTwo to Cy Tolliver, but Cy's unpredictable temper and mistreatment of both Eddie and Joanie lead to Eddie abandoning him.
* NumberTwo: To Cy, initially. Eventually Cy drives him away with his too-frequent displays of violence and a particular moment of public humiliation.
* PutOnABus: At the end of Season 1, Eddie steals from Cy and flees Deadwood, never to be seen again.
[[/folder]]
!!!Bella Union Sex Workers
[[folder:Tess]]
!!Tess
->'''Portrayed By:''' Creator/ParisseBoothe
[[/folder]]
[[folder:Lila]]
!!Lila
->'''Portrayed By:''' Creator/MeghanGlennon
* TheStoner: She's addicted to opium.
[[/folder]]
[[folder:Janine]]
!!Janine
->'''Portrayed By:''' Creator/SarahPachelli
* TheChewtoy: She becomes one for Cy, who alternates between speechifying to her and abusing her.
[[/folder]]
[[folder:Doris]]
!!Doris
->'''Portrayed By:''' Creator/EricaSwanson
* TheMole: Cy employs her to spy on Joanie and Maddie's new enterprise while working for them. Joanie sees through her right away, to the point where it almost seems like Cy wanted her to know.
* SlashedThroat: At Wolcott's hands.
[[/folder]]
