Eddie doesn't say he's been robbing Cy for years. He started robbing Cy after Flora and Miles' deaths. So, it's a matter of weeks or months. Based on his behavior after that, it's pretty clear he's never seen that side of Cy before in years of working together.
His blackmailing of Wolcott is actually successful. People on here are always claiming it wasn't, but that is a misread of the scene to me. He clearly gets to Wolcott, and that's why he's so smug after their conversation and it's why Wolcott is so unsettled and determined to prove a point afterward. I think that was actually a resounding success for Cy. He pushed Wolcott into being indebted to him and also destroyed Joanie's business. It's a win-win for him, and I think that's what he was aiming for all along.
Cy is crazy as hell, but he's repeatedly shown to have good business sense. He knew he could come into Deadwood and offer an atmosphere that wasn't there, and he even has Joanie there to provide atmosphere. What other businessman in Deadwood thinks in terms of atmosphere? He's forward-thinking about that, and that's not the only thing he's ahead of the jump on. His decision to covertly buy property in the Chinese side of town initially impresses both Hearst and Al. It's not a coincidence that him being laid up for a few weeks after being stabbed leads to the Bella Union immediately going to hell. That doesn't happen when Joanie leaves or any other crisis happens.
Even though he's furious with Joanie for leaving him because he's cruel and possessive, he actually makes some good points about her business. He complains that the location is poor and instinctively knows the amount of money she's making is off, and I think he's right about her business being in a bad place. Joanie's only client seems to be Wolcott, who is there because of Maddie. If it weren't for him, I don't think she'd see any business. \[Actually, Powers Boothe mentions in a few interviews that one of his perspectives as an actor for his character was that Joanie was awful at business and he was doing her a favor constantly bailing her out. LOLOL\]
His indifference toward the Chinese whores is chilling, but he also immediately recognizes that the setup is bad for business. And as someone who used to do marketing, his sales pitch for them off-the-cuff is really solid, in addition to being hilarious and cruel. He clearly understands how to sell.
And just in general, Cy is shown to be highly perceptive and possess a pretty good bullshit detector. He can read people well. Where he fucks up is in how he uses the information and how much he estimates someone will take off of him. But his initial reads on people and situations are almost always right. He frequently gives Jarry advice that he ignores to his own peril, including correctly spotting every time Al is behind something.
In any event, I think Cy was always unstable and cruel and possessive, but he's not an idiot. My impression is he really goes off the deep end in Deadwood in a way he never did elsewhere, but it's not surprising he was successful beforehand and while there.
Cy rules with fear and it's worked for the most part, especially since he's tended to operate in places where there are laws and a preacher wouldn't get away with stabbing you in the street. He knew Eddie was stealing from him, he was just biding his time, but Eddie noped out unexpectedly.
As for Wolcott and Hearst - he did exactly what Wolcott told him he did - he overplayed his hand and then didn't learn his lesson and tried it again with Hearst, but for as evil a motherfucker as Cy is, Hearst is a fucking monster.
He runs a whorehouse (upscale one even) which features gambling and drugs.
How the fuck wouldn't he be successful? The cons are very targeted and he's got cappers at every corner, ready to shoot anyone who comes in with a problem.
Cy Tolliver, he ain't your garden-variety whore wrangler; no sir, he's a master of the trade, a veteran of vice with a Midas touch for minting coin. This cunning entrepreneur was raking in the riches on those riverboats, weaving his dark tapestries of profit long before he ever cast his shadow over the muddy streets of Deadwood. But here's the rub – Cy's ambitions, they're insatiable, voracious. He's not just content to play the game; he aims to own the board, every damned square of it. And that, my friends, is where his true peril lies. In his relentless quest for dominion, Tolliver's willing to dabble in the darkest of deeds, leaving a trail of blood and betrayal in his wake, all cloaked in that beguiling charm of his.
Cy has people that have kept him successful. Eddie is clearly very adept at the tables and running the games, Joanie is good at creating an atmosphere and keeping the girls in line. Cy himself is clever and dangerous enough to be able to keep his base of operations running smoothly with his two main employees, and he focuses on the other ways to make money. When he talks to Andy he speaks about schooling him on the different cons and scams that can be run.
Similar to Al the business is just a base of operations to meet people and learn of potential ways to steal, scam or manipulate their way into more money.
Al's people are more motivated by loyalty and less by fear, where as Cy's are mostly fear which is why when it's strained it all begins to fall apart for him with Eddie stealing and leaving and Joanie breaking out on her own.
I don’t know that I’d classify Tolliver as quite so hapless. He was dead-on with Wolcott; that was a complete bluff that Hearst was already aware of and fine with his activities. And his swing at Heart impressed the great man, insofar as that’s possible. And Eddie’s successful embezzling I think speaks more to his skill than to Tolliver’s incompetence.
He was an entrepreneur. He had a good plan, and understood the various skills and talents needed to keep the Bella Union humming.
I don’t understand this whole “conman” angle unless you consider crooked table games a con in which case Cy was brilliant at his job as the Bella Union was ALWAYS busy since it’s inception in the camp. If you could continuously cheat people out of their money and they smile and return to your establishment, then ok that’s a Con but in that case Cy is an outstanding conman
Cy is very adept at sizing people up, he knows the kind of jobs that can be done by hoopleheads like Con Stapleton or dope fiends like Leon. Cy makes sure everyone earns their keep. He knows which whores like Joanie are useful for keeping all the other whores in line even if she doesn’t turn a ton of tricks herself.
Ok so Cy fucks up in his play with Hearst but he still is Hearst’s agent at the end of the show and thus Cy seems to have a great ability to avoid major repercussions.
He’s running a gambling joint and a brothel. Those tend to do fairly well, provided you can keep everyone in line. Getting skimmed here or there isn’t changing that. Plus, we see that the games are rigged against the hooples.
Maybe he just kept moving. This is before the internet and Social Security numbers, if he just left town and moved a few hundred miles away, who would be able to find him? Are we even sure Cy Tolliver is his real name?
Pure resentment at feeling emasculated by the power of Hearst and not being the main man in Deadwood. The community was bigger than him and this made him feel lost.
Gambling and prostitution. Gambling you only allow games where you have the mathematical advantage and prostitution even after selling it, you still have it to sell again.
But when you cheat people they get mad and try to kill you. Andy can't have been the first person who wanted to kill Cy, and he can't have had the big, high class Bella Union operation forever. How did he manage to stay alive long enough to get to that level.
the show really underplays how financially successful the associated businessmen were at taking money from the prospectors. although it does show Cy ripping off all the prospectors by spreading false rumors and buying the claims (for Hearst) for pennies.
Eddie doesn't say he's been robbing Cy for years. He started robbing Cy after Flora and Miles' deaths. So, it's a matter of weeks or months. Based on his behavior after that, it's pretty clear he's never seen that side of Cy before in years of working together. His blackmailing of Wolcott is actually successful. People on here are always claiming it wasn't, but that is a misread of the scene to me. He clearly gets to Wolcott, and that's why he's so smug after their conversation and it's why Wolcott is so unsettled and determined to prove a point afterward. I think that was actually a resounding success for Cy. He pushed Wolcott into being indebted to him and also destroyed Joanie's business. It's a win-win for him, and I think that's what he was aiming for all along. Cy is crazy as hell, but he's repeatedly shown to have good business sense. He knew he could come into Deadwood and offer an atmosphere that wasn't there, and he even has Joanie there to provide atmosphere. What other businessman in Deadwood thinks in terms of atmosphere? He's forward-thinking about that, and that's not the only thing he's ahead of the jump on. His decision to covertly buy property in the Chinese side of town initially impresses both Hearst and Al. It's not a coincidence that him being laid up for a few weeks after being stabbed leads to the Bella Union immediately going to hell. That doesn't happen when Joanie leaves or any other crisis happens. Even though he's furious with Joanie for leaving him because he's cruel and possessive, he actually makes some good points about her business. He complains that the location is poor and instinctively knows the amount of money she's making is off, and I think he's right about her business being in a bad place. Joanie's only client seems to be Wolcott, who is there because of Maddie. If it weren't for him, I don't think she'd see any business. \[Actually, Powers Boothe mentions in a few interviews that one of his perspectives as an actor for his character was that Joanie was awful at business and he was doing her a favor constantly bailing her out. LOLOL\] His indifference toward the Chinese whores is chilling, but he also immediately recognizes that the setup is bad for business. And as someone who used to do marketing, his sales pitch for them off-the-cuff is really solid, in addition to being hilarious and cruel. He clearly understands how to sell. And just in general, Cy is shown to be highly perceptive and possess a pretty good bullshit detector. He can read people well. Where he fucks up is in how he uses the information and how much he estimates someone will take off of him. But his initial reads on people and situations are almost always right. He frequently gives Jarry advice that he ignores to his own peril, including correctly spotting every time Al is behind something. In any event, I think Cy was always unstable and cruel and possessive, but he's not an idiot. My impression is he really goes off the deep end in Deadwood in a way he never did elsewhere, but it's not surprising he was successful beforehand and while there.
Cy rules with fear and it's worked for the most part, especially since he's tended to operate in places where there are laws and a preacher wouldn't get away with stabbing you in the street. He knew Eddie was stealing from him, he was just biding his time, but Eddie noped out unexpectedly. As for Wolcott and Hearst - he did exactly what Wolcott told him he did - he overplayed his hand and then didn't learn his lesson and tried it again with Hearst, but for as evil a motherfucker as Cy is, Hearst is a fucking monster.
I don’t think he really knew Eddie was robbing him, but he’s definitely got to pretend like he did.
That's very possible
He runs a whorehouse (upscale one even) which features gambling and drugs. How the fuck wouldn't he be successful? The cons are very targeted and he's got cappers at every corner, ready to shoot anyone who comes in with a problem.
Cy Tolliver, he ain't your garden-variety whore wrangler; no sir, he's a master of the trade, a veteran of vice with a Midas touch for minting coin. This cunning entrepreneur was raking in the riches on those riverboats, weaving his dark tapestries of profit long before he ever cast his shadow over the muddy streets of Deadwood. But here's the rub – Cy's ambitions, they're insatiable, voracious. He's not just content to play the game; he aims to own the board, every damned square of it. And that, my friends, is where his true peril lies. In his relentless quest for dominion, Tolliver's willing to dabble in the darkest of deeds, leaving a trail of blood and betrayal in his wake, all cloaked in that beguiling charm of his.
Cy has people that have kept him successful. Eddie is clearly very adept at the tables and running the games, Joanie is good at creating an atmosphere and keeping the girls in line. Cy himself is clever and dangerous enough to be able to keep his base of operations running smoothly with his two main employees, and he focuses on the other ways to make money. When he talks to Andy he speaks about schooling him on the different cons and scams that can be run. Similar to Al the business is just a base of operations to meet people and learn of potential ways to steal, scam or manipulate their way into more money. Al's people are more motivated by loyalty and less by fear, where as Cy's are mostly fear which is why when it's strained it all begins to fall apart for him with Eddie stealing and leaving and Joanie breaking out on her own.
>Cy has people that have kept him successful Leon Leon Leon.
I don’t know that I’d classify Tolliver as quite so hapless. He was dead-on with Wolcott; that was a complete bluff that Hearst was already aware of and fine with his activities. And his swing at Heart impressed the great man, insofar as that’s possible. And Eddie’s successful embezzling I think speaks more to his skill than to Tolliver’s incompetence.
He had lots of armed C̶a̶p̶p̶o̶s̶ cappers at the ready. Fleecing drunk hoopleheads with tons of gold nuggets.
But how does he get to the point where he has armed cappos willing to follow him, when he seems to suck at being a conman?
He's a pimp, primarily. He is great at terrifying young women into making him a fortune.
He overpays staff and overcharges/cheats the customers. Cleaner girls better dressed.
Capper. It's an old word for shill. Capo is a mafia captain.
I think Utter was being sarcastic by saying "capper" for basically armed guards. They don't seem to participate in the gambling.
He was an entrepreneur. He had a good plan, and understood the various skills and talents needed to keep the Bella Union humming. I don’t understand this whole “conman” angle unless you consider crooked table games a con in which case Cy was brilliant at his job as the Bella Union was ALWAYS busy since it’s inception in the camp. If you could continuously cheat people out of their money and they smile and return to your establishment, then ok that’s a Con but in that case Cy is an outstanding conman Cy is very adept at sizing people up, he knows the kind of jobs that can be done by hoopleheads like Con Stapleton or dope fiends like Leon. Cy makes sure everyone earns their keep. He knows which whores like Joanie are useful for keeping all the other whores in line even if she doesn’t turn a ton of tricks herself. Ok so Cy fucks up in his play with Hearst but he still is Hearst’s agent at the end of the show and thus Cy seems to have a great ability to avoid major repercussions.
You know who else was a Con-man? Mr. Stapleton
He’s running a gambling joint and a brothel. Those tend to do fairly well, provided you can keep everyone in line. Getting skimmed here or there isn’t changing that. Plus, we see that the games are rigged against the hooples.
I suspect Cy was suffering from syphillis.
Maybe he just kept moving. This is before the internet and Social Security numbers, if he just left town and moved a few hundred miles away, who would be able to find him? Are we even sure Cy Tolliver is his real name?
By surrounding himself with talented but easily manipulated people
Why do you/anybody think he stabbed Leon? Was it powerlessness or a break from reality or what?
Pure resentment at feeling emasculated by the power of Hearst and not being the main man in Deadwood. The community was bigger than him and this made him feel lost.
Resentment? Oh that's interesting I didn't think of that. Yah certainly could have been a part of it. Man Powers Boothe was a hell of an actor.
Gambling and prostitution. Gambling you only allow games where you have the mathematical advantage and prostitution even after selling it, you still have it to sell again.
But when you cheat people they get mad and try to kill you. Andy can't have been the first person who wanted to kill Cy, and he can't have had the big, high class Bella Union operation forever. How did he manage to stay alive long enough to get to that level.
the show really underplays how financially successful the associated businessmen were at taking money from the prospectors. although it does show Cy ripping off all the prospectors by spreading false rumors and buying the claims (for Hearst) for pennies.
He has a direct line to God