Curse of Isiaso

It's stated that the holder of the chessboard can never lose when playing on the side of the demons, but can they ever really win at anything? I would just like to point out that the converse of "not losing" is "losing", and not "winning". Such actions intended for good (playing the saints side of the board) will always fail, and those involving the expense of another (playing the demons side) will never lose. This seems to be a classic tale of good and of evil with a moral to the story. While good may not always prevail, bad may not always win either. Even if it appears that evil will reign victorious, there are downfalls, consequences, curses.

However, I wonder if Bobby Lennin is cleared of the curse at the end. Assuming that the group of "rough-looking characters" would still work as a group, they probably would've come back together. BUT, the narrator says "I heard a gunshot" and closes. I wish we had more! If there was only one shot, did he have a knife, sword, or bludgeon that could draw blood? Blood must be spilled from all perpetrators in order for the curse to be lifted, yet there was only one shot. Did he just give in to an eternity of pain and torture? Did the aforementioned characters shoot him before he could enact his defense and damn him to a hellish existence? Does he ever make it back to the boat, or does he paddle back to the island?