Agent Andrew Milton

Milton is a high-ranked detective in the Pinkerton National Detective Agency. After Dutch robs his train, Leviticus Cornwall hires Milton and his protégé, Agent Ross, to track down the Van der Linde gang and bring Dutch van der Linde to justice. Milton and Ross approach Arthur Morgan whilst he teaches Jack Marston fishing, at a river near Horseshoe Overlook. Milton offers Arthur a chance to surrender and turn Dutch in, in exchange for amnesty. When Arthur refuses, Milton reveals that they captured Mac Callander after the Blackwater ferry robbery and killed him slowly, enraging Arthur. He then proceeds to leave with Ross. Milton and Ross approach Dutch and his gang at their camp in Clemens Point. Milton offers Dutch a chance to surrender in exchange for the other gang members being allowed to escape. Dutch mockingly feigns compliance and the gang all begin to draw their weapons; flustered, Milton warns Dutch that he will be back with fifty men and that the gang should leave quickly. During the bank robbery in Saint Denis, Milton captures Hosea Matthews while he orchestrates a distraction and holds him hostage outside the Lemoyne National Bank, which the Pinkertons have surrounded. Milton states that any reservations for making deals have been exhausted, and subsequently shoots Hosea in the chest, killing him almost instantly. A skirmish ensues, but the Van der Linde gang eventually manages to escape. Milton and his agents pick up Micah Bell after he, Dutch, Arthur, Bill, and Javier return from Guarma, and Micah becomes an informant for the agency. Subsequently, a large group of Pinkertons led by Milton attack the gang's hideout in Lakay, who orders a house that the gang has sought refuge in to be riddled by a Maxim Gun. Despite Milton's best efforts, the gang manages to repel the attack. Along with Ross, Milton meets with Leviticus Cornwall in Annesburg. Cornwall scolds him for his lack of progress and threatens to withdraw his funding. Milton insists that the Pinkertons are "very close" but Cornwall is dismissive; Milton then leaves with Ross, shortly before Dutch confronts Cornwall. While the Van der Linde gang are robbing a train, Milton captures Abigail and holds her hostage at the Van Horn Trading Post, prompting Arthur and Sadie Adler to rescue her. However, Sadie gets captured by Milton, and Arthur is forced to confront the Pinkerton agent himself. Milton sneaks up behind Arthur and holds him at gunpoint; he then reveals that Micah had betrayed the gang, feeding the Pinkertons with information ever since he and the gang came back from Guarma. In response, Arthur grabs Milton's gun, but is quickly overpowered due to his tuberculosis, with Milton pointing his gun at Arthur's head. Before Milton can pull the trigger, Abigail manages to break free of her confinements and shoots Milton in the temple using Sadie's revolver, killing him instantly and saving Arthur. Despite Milton's death, the Pinkertons, now led by Edgar Ross, continue their hunt for the remainder of the Van der Linde gang. Milton is shown to be a strong believer in the inevitable progress of civilization. His philosophy is best summed up by one of the first things he says to Arthur Morgan: "I enjoy society, flaws and all." He despises Dutch van der Linde, believing him to be a "savage" and a parasite that preys on the civilized and weak. He is ruthlessly determined to see Van der Linde suffer for his crimes, to the point where he is willing to allow some degree of clemency for his gang members if they turn him in. Despite his stature in a government backed organization, it can be said that Milton is just as ruthless as the outlaws he hunts. He outright executes Hosea Matthews after he surrendered and was captured, and opened fire with a Maxim gun on a wooden hut housing a child and numerous unarmed people. He even considered giving them a chance to surrender before shrugging and deciding to slaughter them regardless. He also chuckled at a terminally sick Arthur and taunted him in his attempt to kill him. In short, Milton is sadistic, obsessive, irascible, self-righteous, and ambitious. There is evidence that his subordinate agents dislike him, as in the mission “Dear Uncle Tacitus”, an agent quips contemplatively that he'd "like to find a poisonous snake for [Milton]". Adding to his disagreeable personality, Milton is explicitly racist. He is proud of the government's genocide of the Native Americans and calls Lenny "boy", while being disgusted by his touch. Just about Milton's only redeeming trait is that he's confined to the law, a standard that Cornwall - his employer, ironically - doesn't hold in comparison. Milton is a lean man with a pockmarked, clean shaven face, his dark brown hair is kept closely shaved at the sides and neatly slicked back on top, his modern haircut likely reflects his affinity for 'progress'. He dresses smartly and neatly - consistent with the other Pinkerton agents. Donning a dark grey lounge coat with black lapels, to which he pins his badge, along with a crisp white shirt with a navy silk tie, a pinstriped red waistcoat, black slacks, and a black bowler hat with a deep red silk band, as well as black leather gloves, and polished black leather shoes.