Mafia III

While you play through the main storyline of the DLC, Roxy will eventually mention something about the re-election billboards all around town. For the purposes of this achievement, you must destroy at least ten of them at any time during your playthrough. Fortunately, you can destroy the same sign over and over again (they respawn if you drive ~500m away and return).

The only way to destroy the billboards, however, as you will soon realize they are nowhere near ground level, is to drive right through them. During the "Kickin' Up Dust" mission, you should also come to realize that most of these billboards are positioned near ramps, be it within the town, at the fair, or on the outskirts of town. Thus, driving up the ramp and accelerating right through the billboard will ensure its destruction.

Once you have destroyed ten billboards (even if it's the same one ten times), this achievement will unlock.