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Bella Union
Ownership
Tolliver
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Joanie
See Main Characters
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.
Whores
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.
