|“||They weren't Christians... so I sent 'em to hell!||„|
|—Jon ranting about the Indians|
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, and claims to have massacred bison as well.
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. If the protagonist wears the hat in subsequent encounters with Jon, he will attack them instantly.
- He looks similar to the Sasquatch Hunter from the first Red Dead Redemption. As such, he also has a similar appearance to the Sasquatch Hunter from Grand Theft Auto V.
- The hat he wears during the epilogue appears to differ from the one he wears during the previous chapters of the game, since it won't glow on the ground and it cannot be saved in the wardrobe if picked up.
- He is much harder to take down compared to other NPCs.
- In addition to disliking Natives, he also holds a grudge against the inhabitants of Valentine, as well as the drinks in the saloon. It would appear he dislikes many more demographics.
- Attacking him first will trigger a wanted level, although during the fight, the lawmen will simply wait and watch until the fight is over, before asking the player to move along. Alternatively, the player can also fight him by bumping into him when he leaves the saloon.
- After exiting the saloon he will simply pass out on the ground between the Saloon and the General Store. If bumped into, he will wake up and ride away on a horse if one is available, or simply walk away.
- If the fight with Jon goes outside the saloon, he may pull out a hunting knife. This can also happen if the player draws a weapon of their own or tries to evade him.
- Sometimes, a glitch may occur when Jon's attack on the player may trigger too late. During this time, if the protagonist sits at the poker table, Jon will stand next to the player in a fighting pose until the player leaves the poker table.
- Jon looks considerably older in 1907 than he does in 1899, with greyer complexion and more aged skin, as well as being blind in his left eye. This can be attributed to a supposedly rough lifestyle and heavy drinking.
- "You ain't worth two shits, the whole damn lot of ya! Ain't worth one tree... not one buffalo... one redskin. I shot nineteen of them, once. Buffalo, not redskins. Dunno how many redskins I killed... but... they deserved it." – Jon when encountered for the first time.
- "Ain't no 'wild west' no more around here... ain't nothing! Nothing nice. Just more goddamn America... more goddamn shops. More goddamn prissy women, in men's clothing... and women in women's clothing, thinking they must be men! My old Bessy, she could skin a bear with her teeth, so help me God! Look at you... you all make a feller sick!" – Jon insulting the inhabitants of Valentine during the first encounter with him.
- "Quick! Before I shit right here in the bar... 'cause that's how it was back in the day, you know? Wouldn't merely piss indoors... we'd shit and everything... and we didn't care... you know why? Because real men don’t care where other men turd! And that's just a fact. The other side of it is... if you do care, you ain't no man at all!" – Jon when encountered again.
- "Hey, you been watering down the whiskey again? It's a goddamn disgrace!" – Jon to the bartender.
- "Goddamn annoying ladies... all of ya! You ain't men.. now, I fought fifty injuns... you lot whine if a bear comes in your yard. Hell, bear comes in my yard... I eat 'em! I ate an injun once... once I ate a priest as well... said I was heathen so I showed him how much heathen I was. Grilled the old bastard right where the stockyards are now!" – Jon ranting next to the bartender when encountered again.
- "What kind of men are you? Hmm? Momma's boys! Whiners! Complainers! I had a complainer once... heading out west, on the trail to Lanahasse in '68... we sold his liver to the injuns. And then, we ate him when it got cold and I'll tell you what, he tasted like shit. Which was only about right because he was a turd of a man. A goddamn turd." – Jon's drunken monologue during the following encounters.
- "Valentine? No, they should have called this dump "Turd Town"! I mean, I remember when this place was so wild, even the wolves was scared... and the only thing to drink was fresh blood. Now? It's all about churches and shops and all this other bullshit." – Jon lambasting the state of Valentine.