German case syncretism is often assumed to be the accidental by-product of historical development. This paper contradicts this claim and argues that the evolution of German case is driven by the need to optimize the cognitive effort and memory required for processing and interpretation. This hypothesis is supported by a novel kind of computational experiments that reconstruct and compare attested variations of the German definite article paradigm. The experiments show how the intricate interaction between those variations and the rest of the German ?linguistic landscape? may direct language change.