This achievement requires you to complete "Caida Libre".
There is a video guide underneath the text guide if you prefer it instead.
You can start the mission as either Michael or Trevor. Once you start the mission, you will have a cutscene. After it, you will have to go to the observatory. When you arrive, enter the van and aim at the plane into the red square and shoot, do this three times. You will then be switched to Trevor to follow the plane. Try at all costs to be as safe as you can, as if you accidentally fall off your dirt bike, you will probably fail the mission and have to retry from the last checkpoint. When the plane has finally crashed down, approach it and take out a weapon as Javier and someone else will still be alive. Once they are dead, you will get a cutscene and when over, will switch over to Michael. You will now be tasked to destroy the car, don't go in a public area, and also you should probably use explosives than weapons, you shouldn't get a wanted level if you follow these. When you destroy the car, you will be told to meet Trevor at the cement works, once you do, you will get a cutscene. After it, the mission ends.NOTE:
IF YOU DIDN'T GET THE ACHIEVEMENT AFTER COMPLETING THIS MISSION, THEN REPLAY THE MISSION VIA THE "GAME" TAB.
Here is the video guide.
Credit for the video to GAMING BOTTENE ( https://www.youtube.com/channel/UCXxARCrM7MQft6ztaOqiU7g