Jon hunted Indians at some point in his past. He massacred those he encountered, and even claims to have eaten the heart of one. He can be heard audibly expressing his hatred towards the Native Americans.
From Chapter 2 onward, he loiters around Smithfield's Saloon in Valentine. Jon only appears here between the times of 12 PM and 6 AM. He can be seen sitting at one of the tables, drinking and ranting about the Indians, among other ethnic groups.
As he loudly rants about the Indians, the player is eventually given the option to antagonize him. If the player stares directly at him after this, he becomes irritated and will attack the player with his fists.
If he is knocked down during the fight, his raccoon hat will be knocked off his head, which can be picked up by the player and kept.