how is the squires letter bad

I think the Squire shows himself to be resourceful but a little naive as well. He seems quite pleased with himself at securing the ship (HISPANIOLA.) as well as her crew. He boasts of the ease which he did it but really did not check who the crew might be. The squire is certainly eager but it could be bad in a sense that the Squire is a little too trusting and not cautious enough. The whole process seemed a little too easy to be above board.