Levi Simon

Before 1899, Levi Simon becomes Alberto Fussar's right hand and enforcer on Guarma. He oversees the island's sugar plantations alongside the Cuban military and carries out Fussar's orders without restraint. Armed with a Schofield Revolver, Simon helps maintain Fussar's control over the workers and the island. His belt also holds a whip, an emblem of the violence used to protect the plantation regime.

After Arthur Morgan, Dutch van der Linde, Micah Bell, Bill Williamson and Javier Escuella are shipwrecked on Guarma, Simon leads soldiers who arrest them. He accompanies the prisoners in chains and identifies himself while explaining that Fussar faces troubles on the island. Dutch tries to bargain for their freedom, but Simon insists that the strangers must be checked. He rides away after ordering his men to shoot the captives if they cause trouble.

Simon later joins Fussar and his soldiers as they question Javier. Javier is injured and unarmed, but Simon beats him and threatens further violence to force him to identify the men who arrived with him. Javier gives them nothing. Simon and Fussar leave before the Van der Linde gang attacks the soldiers and rescues Javier from their custody.

During the assault on Aguasdulces, Arthur enters the workers' cabin where Fussar holds the ship captain hostage. Simon attacks Arthur from behind, knocks him down and holds him at gunpoint. Dutch enters and aims his weapon at Simon, only for Fussar to cover Dutch. As the standoff continues, Arthur kicks a rifle to the captain, who shoots Simon in the chest. Simon dies in the cabin.