Wasteland 2: Director's Cut

To get both trophies you must restore the current Mayor of Rodia back to office, then install Chris Van Graas Jr. as the new Mayor. Rodia is a place where the Mayor is caged up by the group of mercenaries he hired for protection, the Leather Jerks led by Lt. Dengler. To start the quest, avoid combat in Rodia and go speak to the Mayor (hug the outer wall of the compound guarded by Jerks) then speak to his son Chris in the distillery. Now simply kill off all the Jerks or better yet, complete all the side quests in Rodia to poison the Jerk leaders first which will help in the fight to defeat the Jerks. Once defeated and after speaking to the Mayor back in his office, Under Old Management will pop.

By speaking to Chris before things went down, you activate his quest to become Mayor. After completing Under Old Management, his quest to become the new Mayor is still active. Simply gun the old Mayor down and you'll get Hell Bent For Leather. Note that if you do not speak to Chris after speaking to the Mayor and then go kill the Jerks, the quest to make Chris the mayor becomes inaccessible and therefore you won't be able to get the trophy.