Was It Worth It?

A short while after completing Collectors Item, Jim will text you telling you to meet him at Ray's. When you get there, Ray has Jim tied up, during the cut scene the Johnny and Jim escape. You start going to Ashley's apartment, when you get near to your destination, Ashley will call you saying Ray has sent some men after you. You can fight them off on your own or call Clay for backup, they will say they have setup a trap, lure Ray's men to the trap and throw a few pipe bombs or grenades at their cars and most of them will have died or been injured, just finish off the rest of them. After killing Ray's men, you're told to meet up with Ashley at the clubhouse. She has some pieces of bad news. First, Jim was also attacked by an assassin, but he wasn't as fortunate as you - he was killed, in addition to another Lost member. Also, your old friend Billy has turned state's in the prison and is threatening to talk and give Johnny up. Johnny tells Ashley to go away and the mission ends successfully.

Note: The "assassin" that killed both Jim and an unnamed Lost member was Niko, during the Ray mission No Way on the Subway.