This is missable, but you can easily avoid that if you follow my tip to retry mission until you get it. You can get it in Chapter 11.
At a point in the story, you will head to a bar with Joe to take out the Irish. If you can, take a fast car. Joe will try to go to his car, but if you get in your own, he will join you.
When you go into the bar, you will have to kill all the people in there. I would recommend going out the back door, when I went out the front, my car had disappeared (could be a general bug, rather than the door though). Go outside, and a car will drive off. Quickly jump in your car and drive after them. I found if I pushed them when they went to turn, they would overshoot it and crash. I then jumped out and shot the driver to unlock this trophy.
SolaceCreed also points out: "The trophy will also unlock if you manage to follow him to his destination and you kill all of his bodyguards with him."
If you lose the car and Joe suggests going back to his place, you should pause and select Retry Mission. This will restart you in the bar so you can try again. If the car is missing when you go outside, Retry Mission. By the time you hot wire a car, you will have lost them.