Weird West: Definitive Edition

Missable if you kill Leila, Shelby or Galen before they become bounty targets.
In this example I'm going to be using Shelby Cross as he's the first potential target you can put a bounty on. During "Copper Mountain Quarry" as the Bounty Hunter you can choose to avoid Shelby by not opening his secret door. Doing this will allow Shelby to get away and a Bounty will be placed on his head by the Marshal. As you move into Chapter 2 as the Pigman you can return to Grackle, access the bounty board and hunt down Shelby at the quest location. Shelby is quite a difficult kill, I recommend knocking him unconscious and finishing him off on the floor. The Pigman's charge ability works well here to stun them for 5 seconds where you can do a takedown on him. Shelby can't be captured, only killed - once killed return to Grackle to claim the bounty and the achievement will pop.