It is broadly acknowledged that semantic bleaching is a prominent concomitant of grammaticalization. The reductive process may remove the core semantic element and lead to an appearance of a marker of seemingly incongruous notions. This article handles one such type of semantic reduction in Korean, the case of the multi-functional connective -cani. Historically, -cani originated from a hortative sentential ending -ca and a connective -ni through morpho-syntactic coalescence eliminating intervening forms. The resultant form -cani was initially employed to signal hortative and causal, but later to mark hypotheticality, contingency and incidentality. The development of the hortative-based connective cani- occurred via two channels: (i) the direct quotation channel and (ii) the complementizer channel. One prominent aspect of the development is semantic change, i.e., a progressive reduction of volitionality. At the outset, its semantics had strong volitive element, i.e., imposition of the speaker's volition on the addressee and the speaker together, the defining characteristic of hortative. In its later development into a marker of hypotheticality, the hortative meaning is significantly bleached and the use becomes highly rhetorical. The speaker is strategically invoking a hypothetical hortative pseudo-quotation in order to make his/her statement more dynamic or vivid. As the form acquires the rhetorical and discursive functions, its volitional semantics becomes further bleached, and it is entirely lost when the form reaches the contingency- and incidentality-marking stages. This paper shows how the speaker's discursive strategy has given rise to the emergence of diverse grammatical functions.