This chapter discusses the demise of dative case and its replacement observed in three types of construction in the history of English from a generative point of view. The constructions to be discussed are the Experiencer construction, dative verb construction, and ditransitive construction. In the Experiencer construction, Experiencer arguments were assigned dative case. After the loss of case morphology, the dative-marked argument was superseded by the prepositional argument, and the preposition is now obligatorily required. In the dative verb construction, objects were assigned dative case, but with the case syncretism, dative objects were replaced with accusative objects. Verbs of this type do not require prepositions. In the ditransitive construction, indirect and direct objects were assigned dative and accusative case, respectively. Indirect objects came to be accompanied with prepositions regardless of their syntactic positions. In Present-day English, however, indirect objects require prepositions only when they are not adjacent to their governing verbs; they do not when they are adjacent to the main verbs. The chapter proposes that these three syntactic changes and the requirement of prepositions can be attributed to the difference in intrinsic properties of the two- or three-layered VP-shell structures assumed for verbs in each construction.