After a botched ferry heist in 1899 results in the deaths of several members, the Van der Linde gang flees Blackwater, forced to leave behind their substantial money stash. Realizing that the progress of civilization is ending the time of outlaws, the gang decides to gain enough money to escape the law and retire. They rob a train owned by Leviticus Cornwall, who responds by hiring Pinkertons led by Andrew Milton to apprehend them. The gang perform numerous jobs and heists, as Dutch continually promises that the next heist will be their last.
Following a deadly shootout in Valentine, the gang relocate to Lemoyne. They meet the Grays and Braithwaites, two warring families potentially hoarding Civil War gold. Dutch pits the families against each other, but his actions are uncovered, resulting in an ambush by the Grays which kills gang member Sean and leads to the Braithwaites kidnapping John’s son, Jack. The gang retaliates against both families and learn that Jack is with crime lord Angelo Bronte, who returns Jack and embraces the gang, but then lures them into a trap. Seeking vengeance, Dutch kidnaps Bronte with the gang and feeds him to an alligator.