Andrew Milton

Andrew Milton is a senior Pinkerton detective who works with Edgar Ross, a younger agent under his guidance. Before the main events of 1899, the pair capture Mac Callander after the Blackwater Massacre. Milton later says that he killed the badly wounded outlaw himself. When Leviticus Cornwall's train is robbed near Granite Pass, Cornwall employs Milton and Ross to find Dutch van der Linde and his gang.

At Horseshoe Overlook, Milton and Ross ride up while Arthur Morgan is fishing with Jack Marston on the Dakota River. Milton offers Arthur protection from the gallows if he gives Dutch up. Arthur refuses, and Milton tells him that Mac Callander died by his hand. The detective predicts the gang's destruction before leaving with Ross.

After the fighting in Rhodes and the destruction of Braithwaite Manor, Milton finds the gang at Clemens Point. He addresses Dutch and his people with Ross at his side, condemning them as outlaws with no place in the country he believes is being built. Milton gives Dutch three days to disappear in exchange for being left alone. Dutch pretends to accept, while the gang reaches for its weapons. Milton threatens to return with fifty men, then withdraws after Lenny Summers confronts him.

Milton next appears outside the Lemoyne National Bank in Saint Denis, where the gang's robbery has been surrounded by Pinkertons. He holds Hosea Matthews prisoner and rejects Dutch's attempt to bargain. Milton releases Hosea into the street, then shoots him dead in front of Dutch and the gang. He leaves his agents to storm the bank as the survivors fight their way out of Saint Denis and escape by boat.

After Arthur, Dutch, Bill Williamson and Javier Escuella return from Guarma, Milton makes an arrangement with Micah Bell, who begins informing on the gang. At Lakay, Milton brings a large Pinkerton force to the camp and claims to offer an arrest. He gives his men five seconds before ordering them to fire. During the attack, Sadie Adler and Arthur move from the house to strike back, but Milton escapes after the gang drives off his men.

Milton and Ross accompany Cornwall to Annesburg, where Milton thanks the industrialist for his hospitality. Cornwall berates both detectives for failing to catch Dutch and dismisses them. Dutch soon kills Cornwall, and the Pinkertons press their pursuit harder. While much of the gang robs a train, Milton captures Abigail Roberts outside Beaver Hollow and takes her to Van Horn, intending to send her away on a murder charge.

Arthur and Sadie go to Van Horn to recover Abigail, but Milton's men seize Sadie and force Arthur into a confrontation. Milton gets behind Arthur with a gun and tells him that Micah has supplied the Pinkertons with information since the gang returned from Guarma. Arthur tries to take the weapon, but tuberculosis leaves him too weak to overcome Milton. As Milton prepares to shoot him, Abigail frees herself and shoots Milton in the temple.