Prowling the filthy streets of Deadwood in a pair of riding boots, an expensive cigar gripped firmly between his teeth, Cy Tolliver was a study in resilience and survival. He didn't become the proprietor of the Bella Union by not getting his hands dirty, and for three seasons on HBO's Deadwood he became further entrenched in the deplorable and the duplicitous. Every game of cards he fixed and every rival he straightened out was in pursuit of prestige, influence, and power.
Initially presented as a foil for Al Swearengen, as Al became more shades of heroic, Cy became more shades of green. Envious of his rival's relationship to other industrial figures in the camp, Cy doubled down on his worst traits. By Season 3, he had become one of the most despicable icons of the series, which had many fans believe the devil had come to Deadwood, and he wore a scarlet coat.
10 HE MADE JOANIE FEEL INFERIOR
Cy purchased Joanie from her father when she was 14, and from that initial callous exchange he made her feel disrespected and lowly. She struggled to build a foundation of acumen from the scraps independence he gave her so that one day she might open her own establishment.
He often dismissed her goals and aspirations as being the folly of a prostitute in Season 1, while also continuing to dangle the possibility of their achievement in front of her with the promise of funding. When Joanie did achieve financial independence in Season 3, Cy still mocked her pursuits, because her success ultimately meant leaving him behind.
9 HE SUCKED UP TO THOSE IN POWER
While the other merchants in Deadwood took up a communal counsel about the affairs of the camp, Cy always had one eye trained on the input of outsiders. He began a partnership with Al in Season 1 as the only other rival to his position, but was fine eschewing that camaraderie when it meant achieving a leg up against him by supporting the objectives of external forces in Season 2.
When George Hearst arrived in Deadwood, Cy truncated his mutually advantageous partnership with fellow entrepreneurs because the gold mogul offered what he perceived to be a status upgrade. He pandered to whomever offered him a larger piece of the pie.
8 HE TRIED TO UNDERMINE AL
Al Swearengen represented a rival that Cy would have to contend with for the purse strings of the camp, and for that he tried to undermine him at every turn, beginning in Season 1 with Wu and other Chinese immigrants from San Francisco.
In Season 2, Cy was the one to get on the good side of George Hearst before Al could broker a partnership, who got his finger chopped off for his blatant disrespect of the titan of industry. Cy also turned a blind eye to his lieutenant Leon stealing from Al's dope supply.
7 HE GOT INCREASINGLY BRAZEN
Cy might have appeared the suave sophisticate beyond reproach because he was never shown to get his hands dirty, but as the series continued, he wasn't afraid to be perceived as the villain he was.
When he killed Flora and Miles, he allowed the information to be leaked to the citizens of Deadwood to highlight his brutality once crossed, but by Season 2, he openly took accountability for having Merrick's newspaper office ransacked without thought of reproach, and did nothing to quell the camp from wanting to string up the government official from Yankton.
6 HE TRIED TO MOLD JOANIE INTO BEING LIKE HIM
Cy was always one to suggest patrons of the Bella Union try their hand at his games of chance, and as a betting man himself, he went all in on Joanie Stubbs. He trained her at a young age to indoctrinate others, give them what they thought they needed, and then cut them loose.
He tried to mold a monster in Season 1 when he wanted Joanie to get rid of their friend Andy Cramed and she refused. Cy had hope he found someone as morally bankrupt as himself, but Joanie refused to be controlled. Even after she started her own establishment he tried to lure her back to the Bella Union, and she was forced to inform him that she'd kill him eventually.
5 HE KEPT LYING
Sometimes Cy lied outright, and sometimes he merely omitted information. In Season 1, viewers came to know him as a rakish entrepreneur who fixed his card and dice games, but he also lied about Andy Cramed being responsible for bringing smallpox into the camp.
By Season 2, he lied about having a letter containing sensitive information about Hearst's right-hand man Mr. Wolcott, and by Season 3, he continued to lie to Doc Cochran about the real reason he kept picking at the stitches from his knife wound.
4 HE BECAME MORE AND MORE PARANOID
Like Al, Cy had a need to know everything that was taking place in Deadwood. Unlike Al, Cy kept being put on the perimeter of information circulation due to his initial reticence to be included and his unlikable qualities.
In Season 2, he became paranoid about Al's relationship with Wu, and in Season 3, he grew worried that Hearst wasn't being as candid with him as he should. It culminated in Cy being notably absent from the gathering in the hardware store in Season 3 when the camp leaders decided to seal Hearst's fate.
3 HE TOOK OUT HIS ANGER ON OTHER PEOPLE
Cy gave the impression of a ticking time bomb, imbuing the quietude of any moment with the potential to erupt. He took out his anger on his subordinates and his enemies alike, with a brutality that indicated unbridled sociopathy.
Not only did he weaponize his rage against Flora and Miles in Season 1 because he felt taken advantage of, but in Season 3, he would verbally berate his newest employee Janeane ("Stupid") because he felt abandoned by Joanie, and shanked Leon because he felt increasingly irrelevant.
2 HE USED JOANIE FOR VALIDATION
Beneath Cy's velvet frock coat, polished riding boots, and expensive cigar was a man who often fought feelings of inadequacy. He circulated in certain groups that offered him political and socio-economic advantages because he felt it would augment his social status.
The only person who knew of his insecurities was Joanie, whom he used for validation off and on throughout the series. When she had a room in the Bella Union, and even when she left it to start her own enterprise, he darkened her doorway to seek her approval even while insulting her for it.
1 HE RAMBLED INCOHERENTLY
Fans have criticized the fact that Cy Tolliver seemed to have a far better character narrative built up behind the scenes than was ever followed through within the series. Much of his dialogue seemed to not make sense in the moment, indicating that it would culminate in a logical and meaningful payoff.
However, whatever nonsensical monologues he had in Season 1 only got worse by Season 3, when a near-death experience made him ramble and rave like a man having a nervous breakdown. Cy spiraled out of control with no rock bottom to hit, leaving fans confounded as to his motivations.
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