Sean was born in Ireland presumably Donegal [1] and spent his early childhood there. Sean's father was Darragh MacGuire , an infamous Fenian outlaw who fled to America with Sean, before being hunted down and killed.
The young Sean was sent to a reform school, but it did little for him. Sean first met Dutch and Hosea at a bar somewhere in North Elizabeth.
After seeing a fancy pocket watch that Dutch had, Sean followed the pair into the dark alleyway and threatened them at gunpoint. Much to Sean's surprise, both Dutch and Hosea simply laughed and dared Sean to shoot them, which he did. It turned out that the pair had spotted Sean first and silently taken the bullets out of Sean's gun. Instead of killing him, Dutch and Hosea decided to give Sean some food and inducted him into the Van der Linde gang. The protagonist can encounter Sean at Tanner's Reach , where he will initially hold them at gunpoint upon seeing them inside the cabin.
Quickly calming himself, Sean begins speaking of having become separated from his group before giving the protagonist a robbery tip on a nearby passing stagecoach. Afterward, Sean can be found again inside his cabin, and will offer paid killings, thefts, jailbreaks, and other coach holdup missions to the player. His missions give negative honor. Sean appears in the Blood Money update as a member of Guido Martelli 's criminal network, and offers new missions to the protagonist.
After the botched ferry robbery in Blackwater , Sean became separated from the others and was one of the few members who did not end up with the gang in their new hideout at Colter. He was subsequently captured by bounty hunters led by Ike Skelding and interrogated for information on the gang, but Sean told them nothing. After moving to Horseshoe Overlook , a new hideout close to the town of Valentine , the gang hears from Josiah Trelawny about Sean's aforementioned apprehension by bounty hunters.
