One type of construction that has always bugged me is the distinction between should (past tense of shall), and its past perfect form. Assume a character, let's call him John:
He lost the poker game. He should have quit while he was ahead, but he didn't listen.
So far, so good. However, moving to past perfect, do I still use the same construction? And if so, are these forms solely distinguished from context?
He had lost the poker game. He should have quit while he was ahead, but he hadn't listened.
This sounds weird to me and I am not sure if it's even correct. My knowledge of English grammar is very intuitive, rather than rule-based, so I was hoping somebody here knew the answer.