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Since the courts avoid the entire issue, it's one that'll probably never be properly addressed. It's a political, not a legal, issue.
I'd argue that it should carry over, for two reasons.
First, if the goal is to ensure that a president gets unfettered, uninhibited advice, which often includes insane scenarios that are rejected but which have to be considered, or which might mean people offer suggestions that would be embarrassing in many ways if it were known who suggested them, there's little difference in having that information come out weeks or years later. Assuming the person's still alive and engaged in similar kinds of professional activities.
Second, while executive privilege isn't in the Constitution, it seems to be modelled in some ways on the Constitutional provision granting legislative papers (etc.) privilege from search and seizure. Does the privilege expire when a bill is finalized, and the papers no longer "strategic" but merely historical? How about when the Congressional session is over? Or perhaps when the Congressperson's out of office? No, s/he can make the papers public, but they stay confidential for a while.
This is a different argument from saying that everything squeezed under the mantle of "executive privilege" properly belongs there. While this is an absurdly obvious--even a ridiculously trite--point, for some reason I thought it necessary to point it out.
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