Some time prior to the year of 1899, Leon was arrested and transported to the island of Guarma to work on the sugar plantation. He eventually joined the uprising on the island and became a member of the rebel faction led by Hercule Fontaine.
Events of Red Dead Redemption 2
When Arthur Morgan and others are captured by soldiers on Guarma, Leon is seen with some rebels who were also captured on the island. When Dutch asks soldiers on who are they and what crime they committed, a soldier states that they are criminals and that their crime was "insurrection".
Leon sarcasticlly replies to the soldier's comment about rebels being arrested for insurrection, and so a soldier tells him to shut up. Soon afterwards, the soldiers are eventually ambushed by Hercule's men. Leon is seen bashing a soldier with a rifle and is later seen helping rebel free himself, before fleeing with the others from military reinforcements.
Arthur is sent by Hercule to rescue some workers who have been captured. Before reaching his destination, Arthur is knocked unconscious by a tranquiliser dart from the Guarman military, resulting in his capture.
Arthur wakes up tied to a chair in some ruins, and while his captor, Angel, is occupied with Baptiste. After Arthur is not forthcoming with answers in regard to his identity, Angel turns to Baptiste in the hope of extracting something from him instead, but Arthur manages to escape from the chair and beats Angel into unconsciousness. Arthur subsequently cuts both Baptiste and Leon free, who had also been captured. Arthur and Leon then venture to rescue some workers who are scheduled to be hanged, while Baptiste stays back due to his injuries. After saving the workers, Arthur and Leon meet up again with Baptiste, and Leon pays Arthur for his help.
- Red Dead Redemption 2