Chisholm is a practical man. He hunts down outlaws for the bounty money. He does his job well, and expects to get paid for it (unless it’s personal, or a “mercy” job). Once hired to clear a town of bad guys, he finds all the best sharpshooters, gunslingers, and potential allies he can and organizes them in town. He offers them money in exchange for their time and effort. He has them train the townspeople to fortify and shoot. He expresses himself with frankness and sincerity. Even though he is intent on torturing the man whose family murdered his family a little bit before he dies, Chisholm sees the rationality in Emma shooting him (to save his life) and thanks her (with a nod). He’s a man of few emotions that come to the surface. Even when men he respects die, he doesn’t cry in front of others, he just asks that they be buried with the respect they deserved. He doesn’t make emotional appeals or talk about how he feels. He just tells the bad guy, to his face, what happened to his family, and wants him to suffer a little. His meticulous attention to details is what keeps them all safe. He’s present and aware of his environment, but also tends to take fewer risks than some of his friends. Chisholm reveals toward the end of the film that much of his motivation for what he does is tied to his past, to what happened to his own family, in another small town. He knows the men he hires, well enough to know they are right for the job. Chisholm thinks in different directions, but for a purpose; he figures out many ways to fortify the town, make it dangerous to those coming in, and protect it from assault, but does not show much intuitive inclination beyond that, except in sensing something is a bit amiss with Goodnight. He sees the bigger picture in crushing bullies in order to make a statement.

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Chisholm is a strong-willed man of confidence and a total lack of fear. He’s smart in how he chooses his men, refuses to let anyone intimidate him (and more often than not, intimidates them), and does not back down from a fight. He respects those who stand up to him, but does not allow their opinions to influence his own. He seeks revenge, as much as justice, and sometimes takes unorthodox methods to obtain it. He has a quiet, side, with his 9 wing not liking conflict for its own sake, and seeing a great many arguments as ultimately pointless. He manages to numb himself to unpleasant things and remains largely unemotional.