Mafia III

This achievement can (and will naturally) be earned on any Racket mission; however, the earliest opportunity is during the first of these missions when you are tasked with tracking down Merle Jackson and taking over his nightclub.

After completing the first objective of the mission - freeing the strung-out girls - return to The Voice. You will then be tasked with taking down Merle's Enforcers, which opens up two secondary objectives marked with red skull icons on the world map. Complete these objectives however you see fit. The first involves eliminating a pimp in an enemy-controlled neighborhood, and the second involves eliminating a pimp at a motel strip.

Once both of these objectives have been completed, the achievement will unlock and you can carry on with the mission. Take note that this works on any Racket mission, but this solution assumes the first mission is where most players will get this done.