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On dead doornails, first some literary history to date expressions.

Shakespeare uses a version of expression in word play between Falstaff and his sidekick Pistol, in Henry IV part 2 "F - what, the old king is dead? P - As nail in door..." So it was already a common expression, or the reference would have sailed over everyone's heads. Not that Shakespeare never aimed high, but here he clearly was aiming as low as possible. The effect he wants is the lowest classes joking over the mortality of kings.

In Piers Plowman in the 1300s, it is dead as a door *tree*, not door nail. "James the gentle, faith without fact, as dead as a door tree, faith without works is dead". Door tree meaning the jamb or post against which the hinges are screwed, and thus this reference is a version of the older phrase "as dead as a post". The fact being exploited is that the term for the jamb used the word for a living tree within it, and that brought out the contrast between living wood and dead wood.

The historical progress is from a piece of wood used as a post no longer being a live tree, to a piece of wood used as a post as the side of a door as a particularly artificial and used, inanimate bit of wood (despite its living-like "tree" name), and from post to doorpost.

The doorpost became a doornail in the expression sometimes between the 1350 and 1600. The iron of the nail is clearly even less alive than the wood of the post, that is the main motivation for the continued direction. This transition undoubtedly benefited from a second sense of "dead" applied to nails in carpentry. Which is the term used for a nail that has been driven through a board and then bent over on the far side of it to create a permanent fastening; the bent nail is said to be "dead" because it cannot be removed to be reused.

So posts are dead because they are no longer living trees; posts that aren't living trees get connected to doors by the term door-tree for the jamb; nails bent over are dead nails because they cannot be reused.

FWIW.

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