This achievement can be attained easily through either Michael or Trevor. The Martin Madrazo mission "Caida Libre" will become available 3/4 of the way through the story mode. All you have to do from here is complete the mission and achievement will pop.
If you have already beaten the mission and did not get the achievement, you can pause the game and go to the missions tab. From there you can find the mission Caida Libre.