In English, there are a couple of words whose categorial status is murky, the most notable of which is near. It is sometimes referred to as a preposition (Svenonius (2010)), as a transitive adjective (Maling (1983)), or as an intransitive adjective whose PP complement happens to be filled by an empty P (Kayne (2005)). The first aim of this article is to show that the three analyses are all correct synchronically in that they represent a different stage of grammaticalization on the cline from transitive adjective to intransitive adjective to preposition, on the basis of the newly discovered fact (i) that the semantic gradability of near began a sharp declination from the late 19th century, (ii) that its morphological compatibility with the preposition to also began a sharp declination from the same period, and (iii) that its collocation with the adverb right became possible around the same period, among others. The second aim of this article is to provide a syntactic analysis of the grammaticalization of near, with recourse to the insights put forth by Waters (2009) as to the grammaticalization of inside from N to Axial Part to P.