Wait, so we've got three separate bets going on here?
No, apparently I was mistaken:
All the same, Based on the OP, I'd wager Pirate's going to end his deal, one way or the other, on August 14th. If the meetup is on the 13th (sorry, I can't remember), then that would indicate that Pirate wants out of his bet before then. The only reason I can think of is that he predicts that he will run out of money around that time.
Or, he could just be being nice, and offering a way for Van to save face.