This is an easy one, and there are two ways to do this. The first is that you give Jack the bribe money as you progress through the game, and the second is that you give Jack the bribe money after you beat the game by means of chapter replay.
Whichever way you choose, there are some certain things you'll have to keep in mind:
- Jack is not always the one who comes out. In fact, usually it's Gina, who of course yuo can't bribe. In order to get Jack to come out so you can bribe him, just keep pulling in to the gas station and exiting if it's Gina, then keep going back in until Jack shows up.
- You will not have to bribe Jack ten times. The price of the bribe goes up every time you do it.
- You cannot bribe Jack more than once per chapter.
- The chapters you can complete the quest on are 2, 3, 4, 6, 7, 8, 9, 11, 12, 13, 14, 15, 16, 18, and 26.
Basically, the first method is self-explanatory. As you move through the game, don't forget to go by the gas station when possible and bring Jack out so you can bribe him. This will be the option for people who have not played through the game yet.
The second method is how I got this trophy, and it's probably how many others will get it when they start hunting for the platinum. If you've already beaten the game, simply replay any chapter where you can go the gas station, bribe him at some point during that chapter, and then complete the chapter to save your progress in the mission. Repeat this until you've gotten the trophy. You'll know that you're doing it right when you notice the price of the bribes going up.
For the second method, I recommend using Chapter 26, the last one. It's a very short chapter, allowing you to complete it quickly after you bribe Jack.
The trophy will pop after you complete the sidequest.