|“||I enjoy society, flaws and all. You people venerate savagery, and you will die savagely! All of you!||„|
|— Andrew Milton regarding the Van der Linde gang|
Milton is a detective in the Pinkerton National Detective Agency. After Dutch robs his train, Leviticus Cornwall hires Milton and his subordinate, Agent Ross, to track down the Van der Linde gang and bring Dutch van der Linde to justice.
Events of Red Dead Redemption 2
Horseshoe Overlook chapter
Milton and Edgar Ross approach Arthur Morgan as he was fishing with Jack Marston at a river near Horseshoe Overlook. He 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.
Clemens Point chapter
Milton and Ross approached Dutch and his gang at their camp in Clemens Point. He offers Dutch a chance to surrender in exchange for a head start for the other gang members to leave. Dutch pretends to comply, but the gang all draw their weapons. Flustered, Milton warns Dutch that he will be back with fifty men and that the gang should leave quickly.
Saint Denis chapter
During the bank robbery, Milton captures Hosea Matthews and holds him hostage outside the Lemoyne National Bank, which Milton had surrounded as the Van der Linde Gang were robbing it. Milton states that any reservations for making deals have been exhausted, and subsequently shoots Hosea in the chest, killing him. A gunfight ensues and the Van der Linde gang eventually manages to escape.
Milton and his agents pick up Micah Bell after he, Dutch, Arthur, Bill, and Javier come back from Guarma. Micah becomes an informant for the agency. Later, almost certainly thanks to Micah’s information, Milton attacks the gang's hideout in Lakay, ordering the house the gang was holed up in to be riddled by a Maxim gun. Despite his best efforts, the gang manages to repel the attack.
Beaver Hollow chapter
Milton meets with Leviticus Cornwall in Annesburg. Cornwall scolds him for his lack of progress and also threatens to pull his funding. Milton leaves with Ross, shortly before Dutch confronts Cornwall.
Milton later 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 Milton himself. Milton sneaks up behind Arthur and holds him at gunpoint. He reveals that Micah was the rat all along, having started talking after they picked him up shorty after the gang came back from Guarma. Arthur grabs Milton's gun, but is unable to overpower him due to his Tuberculosis. Fortunately, Abigail manages to break free of her confinements and shoots Milton in the temple using Sadie’s revolver, killing him before he can execute 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 and desirable progress of civilization. His philosophy is best summed up by one of the first things he says to Arthur: "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 Dutch suffer for his crimes, to the point where he is willing to allow some degree of clemency for 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 gangs 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 women. He was even thinking about giving them a chance to surrender before shrugging and deciding to slaughter them regardless. In short he is sadistic, obsessive, irascible, self-righteous, and ambitious. It could be speculated as well that his fellow Pinkerton agents dislike him (and vice-versa), as in the mission “Dear Uncle Tacitus”, an agent quips contemplatively that he'd "like to find a poisonous snake for him." He's also extremely smug up until his death and mockingly cordial with his enemies, in a weak attempt to seem professional. Just about Milton's only redeeming trait is that he's confined to the law, a standard Cornwall doesn't hold in comparison.
Milton is explicitly racist, a given for the setting. He's proud of the government's genocide of the Native Americans and calls Lenny "boy", as well as being disgusted just by his touch.
Milton is clean-shaven, revealing a face full of scars and other deformities, likely from his violent line of work within the Pinkertons. His cheeks are also deeply pockmarked, suggesting that at one point he contracted smallpox or a similar disease. He has a slim build and a "high and tight" haircut, with the sides of his head completely shaved and the top left intact (a very unusual hair cut for a western man at the time). He's never seen outside his Pinkerton uniform; a black business suit and bowler hat, but with distinct red trimmings to help him stand out as a high ranking officer.
- "A Fisher of Men"
- "The Battle of Shady Belle"
- "Banking, The Old American Art"
- "Fleeting Joy"
- "Just a Social Call"
- "Red Dead Redemption"
- Milton's first name is only mentioned in the final issue of The Blackwater Ledger and in the ending credits of the game.
- It is implied that he is disliked among the Pinkerton agents that work under him, as various Pinkertons can be heard making negative comments about him.