[Tormus]

I promise I'm not trying to pick on you... 

Could you clarify that plotline question a bit?  It's better than the first go, but it still comes across as him setting out specifically to mess with other people's plans - to work *against* the storyline instead of take part *with* the story.

Generally he is trying to rob people for his own advantage. In theory preying upon the weak for his own profit. But in practice, he is going to keep hitting a moral threshold that he is unwilling to go beneath.

Robbing Merchants is fine.
But if it turns out the merchant ship is carrying slaves, he might just free the slaves instead, and then spend his own money to help them survive.

And so much of his life is a frustration of trying to be the villain, but continually running into and losing a battle against his conscience.
To put it in alignment terms. He really wants to be Chaotic Evil, but in extreme situations acts Chaotic Good instead.

As far as it goes into the system, he is generally going to support those who agree to work with him / pay him / flatter him the most.
But if the person he is working for does something too morally reprehensible, he will betray them.
The whole time trying to justify to himself that he isn't just a big softie.