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Help Rancher Bob take over the Oil Tycoon's Mansion. After completing the quest he will ask you to go check on Richard (Rancher who stayed behind and Bob's Ranch).
Heading back to the Ranch after the Takeover, you will see that Richard is dying/dead. Go back to Bob and give him the news.
To unlock this, you need to have two interactions with him through a select choice of dialogue.
-Give Bob the news that Richard is dead, ask if he is ok with this. Bob will say his death was not in vain and will slowly become more like the Oil Tycoon.
Reload your save, and do the same steps as earlier, but this time, pull him back from the power. You should say something along the lines of "Do you even remember his name?" and eventually he will see that he is no better than the Tycoon.
This achievement is bugged and you may not get it at first (I had to restart my game and it unlocked after startup).
In any case, my story is similar to Soop-Om's. The achievement didn't pop until I restarted the game. It unlocked immediately on startup. Good luck!
All you really need to do is finish a conversation with Bob after witnessing Richard die in two separate ways: one approving and one disapproving, then restart the game, which is when the achievement should trigger. You can savescum or do separate runs for it.
By the way, the disapproving talk nets better mechanical benefits.