At some point the Captain and his group acquired a helicopter by unknown means. Soon after he put it under heavy guard. In 2027, he made a deal with Boone of the MontroseResistance to use their helicopter. When Connor Morgan, Robert Jacobs, Rianna and Hopper Lee arrived at his camp to retrieve the helicopter, he remarked at Connor being alive, as he had falsely heard the KPA had hung him.
When he learns that Boone is dead, he decides the deal is off. When Rianna protest one of his guards grabs her and holds a knife to her throat. Connor tries to calm him down by reminding them that "they're fighting the same war" but The Captain changes the deal: Connor can take the helicopter if he gives them Rianna (whom he refers to as "the bitch") and Hopper (referring to him as "Scarface"). Connor violently refuses the deal in which Rianna kills the guard before she kills The Captain.