Last night I was pirated by an Outcast in California and paid him. There was another Outcast "with him". I paid his request. Then the Outcast "with him" chased me down and tried to tax me in NY. I said I just paid you guys and he said that they weren't working together. If you're "with" other pirates then are you allowed to double dip like that?
I'd say if they were competing with each other for the same trade ship, and each wanting their own profits they should have fought each other for who gets the ship.
At least that's what some of my characters would do, If I helped pirate a ship and didn't get anything from it...I would deal with that 'ally' of mine, not chase down the trader.
Two people, same spot, same side, working together, best split the profits I'd say.