The Bella Union
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Ownership
Cy
Cyrus "Cy" Tolliver
Played By: Powers Boothe
"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.
- Ambition Is Evil: 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.
- Ax-Crazy: His nifty dress sense and quick smile are a thin veneer for what he truly is: a vicious jackal who kills before thinking.
- Bad Boss: Cy bullies, threatens and outright murders his employees from time to time.
- Big Bad Wannabe: He's essentially a darker version of E.B. Farnum - a Smug Snake 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 George Hearst.
- Bitch in Sheep's Clothing: He can pretend to be civil...for all of five minutes.
- But That Would Be Wrong: 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. -
The Character Died with Him: Implied to have been his fate during the Time Skip 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. - The Dandy: He is well-dressed and groomed, in contrast to pretty much everyone else in the camp.
- Deadpan Snarker: 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."
- Demoted to Dragon: After he sides with Hearst.
- Disproportionate Retribution: 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.
- Even Evil Has Standards: 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.
- Evil Counterpart: To Al. Notable, considering that Al is already evil, but affable.
- Evil Mentor: To Joanie.
- Eviler than Thou: Cy's character is essentially a version of Al that lacks the flickers of humanity that Al demonstrates.
- Faux Affably Evil:
- 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 Faux Affably Evil and Affably Evil, 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 Men, 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'.
- Hair-Trigger Temper: He has trouble keeping his fiery temper in check, and can blow up at people sometimes for no reason.
- Humiliation Conga: 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.
- Incompatible Orientation: With Joanie, who he seems to love. She's a lesbian.
- Jerk with a Heart of Jerk: 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.
- Pet the Dog: Don't expect even the slightest bit of decency from Cy, unless your name is Joanie. He rescued her from her own incestuous, abusive father (although this might just be because Cy 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 Ellsworth killed.
- Politically Incorrect Villain: He stands out even though the show averts Politically Correct History as much as possible. Ironically, he is the only one that claims to 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."
- Sanity Slippage: After being stabbed, his mental health begins to fail and he becomes even more violently unpredictable.
- Smug Snake: Fancies himself a
Magnificent Bastard. 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 Axe-Crazy Bad Boss tendencies only serve to drive away any potential allies, forcing him to rely on clumsy lickspittles and inept junkies who couldn't think their way out of a box. - Surrounded by Idiots: 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.
- Villainous Breakdown: Cy progressively goes through one in Season 3 as a result of Hearst's machinations and the physical after-effects of his stabbing, culminating in a massive explosion of impotent rage in the final episode.
- You Have Failed Me: Has a tendency to do this to his employees.
Joanie
Joanie Stubbs
"I wish once I could care for those little ones. Just once instead of doin' what I did."
Played By: Kim Dickens
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.
- Abusive Parents: Her father raped her and her sisters, before selling her into slavery at the age of 14.
- Broken Bird: 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.
- Deadpan Snarker: 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. - Despair Event Horizon: In Season 1, when Cy forces her to shoot the thief that stole from her. Again in Season 2, when Francis Wolcott kills her business partner and two women more in her brothel.
- Gorgeous Period Dress: Joanie is one of the more fashionable character, usually dressed in a beautiful dress complete with a nifty hat.
- High-Class Call Girl: 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.
- Hooker with a Heart of Gold: She's a prostitute and one of the most kind-hearted characters in the show.
- Lipstick Lesbian: 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.
- Made a Slave: After her mother died, her father prostituted her and later sold her to Cy.
- Miss Kitty: Within the Bella Union. She later tries to strike out on her own with Old Friend Maddie, but things go terribly wrong.
- Morality Pet: To Cy, although he's often cruel even to her.
- Number Two: To Cy Tolliver, during Season 1. After that she strikes out on her own.
- Official Couple: With Jane, eventually.
- Platonic Life-Partners: Becomes this with Charlie.
- Rape as Backstory: Her father molested and pimped her out as a young child.
- Took a Level in Badass: When she beats Francis Wolcott over the head with a bottle.
Staff
Stapleton
Con Stapleton
Portrayed By: Peter Jason
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.
- Age Lift: The real Con Stapleton was in his twenties when he lived in Deadwood; here, he's played by the much older Peter Jason.
- Bumbling Sidekick: 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.
- Dirty Cop: 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.
- Fan Disservice: Seriously, who though that giving Con two 'sexy' scenes in Season 3 was a good idea?
- Heel–Faith Turn: In the ten-year Time Skip between the show and movie, Con has become a Reverend, and it's he who officiates Sol and Trixie's wedding.
- Historical Villain Upgrade: 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 stunts
well far from the pathetic gimmicks of the TV character. - Minion with an F in Evil: 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.
- Took a Level in Kindness: Following the Time Skip, 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.
- Yes-Man: To Cy, who can't stomach outside opinions from his peons.
Leon
Leon
Portrayed By: Larry Cedar
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.
- Bumbling Sidekick: Leon is deeply incompetent, and can at best be cautiously relied on to fulfill menial tasks. Mostly,though, he impedes whoever he works for.
- Butt-Monkey: Not much goes right for him, but it's pretty much entirely his own doing.
- Chronic Backstabbing Disorder: 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.
- First-Name Basis: With everyone. His last name is unknown.
- Harmless Villain: 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.
- Politically Incorrect Villain: 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.
- Professional Butt-Kisser: 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.
- The Stoner: He's an opium addict, motivated entirely by where his next fix is coming from.
- Too Dumb to Live: 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.
- Yes-Man: To Cy.
Eddie
Eddie Sawyer
"Did that blood stain get you the special rate?"
Portrayed By: Ricky Jay
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.
- Affably Evil: Eddie is a con-man who takes advantage of others and has worked alongside proud-and-loud Ax-Crazy 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.
- Ambiguously Gay: 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.
- Creator Cameo: Ricky Jay is a writer as well as an actor (also a magician, which is cool) and he's written episodes of Deadwood.
- Deadpan Snarker: As per usual for a Ricky Jay character; Eddie has a sharp wit that's on-display in every scene.
- The Dog Bites Back: 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.
- Hyper-Competent Sidekick: Eddie is a highly intelligent man who gives Cy valuable advice. When he leaves, it's the beginning of Cy's downfall.
- Minion with an F in Evil: He's a minion of Cy, but he's pleasant, witty and doesn't really do anything evil aside from associating with Cy.
- Mistreatment-Induced Betrayal: Eddie is a pretty loyal Number Two to Cy Tolliver, but Cy's unpredictable temper and mistreatment of both Eddie and Joanie lead to Eddie abandoning him.
- Number Two: To Cy, initially. Eventually Cy drives him away with his too-frequent displays of violence and a particular moment of public humiliation.
- Put on a Bus: At the end of Season 1, Eddie steals from Cy and flees Deadwood, never to be seen again.
Jack
Jack Young
Portrayed By: Nick Amandos
The bartender at the Bella Union.
- Nice Guy: 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.
Bella Union Sex Workers
Tess
Tess
Portrayed By: Parisse Boothe
Lila
Janine
Janine
Portrayed By: Sarah Pachelli
- The Chewtoy: She becomes one for Cy, who alternates between speechifying to her and abusing her.
Doris
Doris
Portrayed By: Erica Swanson
- The Mole: 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.
- Slashed Throat: At Wolcott's hands.
