"…I'll buy you the hat. A really big one. Commodore," Jack finished with a flourish, a wicked half smile on his face Barbossa thought he knew well.
Barbossa allowed his own smirk to replace his skeptical expression. "We have an accord."
…"Me, I'm dishonest. And a dishonest man you can always trust to be dishonest. Honestly, it's the honest ones you have to watch out for, because you can never predict…when they're going to do something incredibly…stupid…"
Oh how easy it would have been to have not been stupid. That would've been the smart thing to do. Pretty straightforward: sail off into the sunset on your ship, captain once more…
…except that you would be partners with the man who mutinied you; except you would have betrayed a young whelp so naïve and stupid but rather charming, really, so he grew on to you. It helped that said whelp's father stood up for you after you were marooned.
Jack maybe one day could have lived with that. Or not. Not without just desserts being served first. He didn't have the will. He would've had to kill Will, actually, and then Lizzie would be heartbroken and would hate him, and Bootstrap would've haunted him.
So no, for once in his life, Jack could not have done the smart thing.
Maybe, if he could somehow get his revenge and then Barbossa came back from the dead, then they could have been partners.
But what's the chances of that happening, right?
