The quantifier viel changes from exhibiting properties of a head in Old High German to exhibiting properties of a modifier in Modern German. This is accompanied by changes in word order vis-à-vis its quantified constituent and the loss of the ability to assign genitive case to some of the quantified constituents. Assuming that quantifying expressions may have various syntactic representations, we argue that viel develops from a quantifying noun to a particle in Card0 to an adjectival quantifier in Spec, CardP, and that this structural change in the position of viel can account in part for the morphosyntactic properties of the quantified element. The development of viel from a quantifying noun to a quantifying particle—a case of head-to-head reanalysis—is typical of grammaticalization. However, the change from a particle to an adjectival quantifier represents head-to-specifier reanalysis, which we relate to degrammaticalization due to analogy with other inflected elements of the DP. The change in word order and case properties of the quantified constituent represents a third type of reanalysis, whereby an embedded nominal undergoes downward reanalysis. Depending on the structural size—that is, whether a DP-layer is present or not—the dependent nominal either integrates into the matrix nominal agreeing with viel or, if too large, it takes up a new embedded position as a complement of the matrix head noun, retaining genitive. We demonstrate that in each case, the morphological change lags behind the syntactic reanalysis.