In this paper, we investigate the interaction of phonological and syntactic constraints on the realization of Information Structure in Greek, a free word order language. We use magnitude estimation as our experimental paradigm, which allows us to quantify the influence of a given linguistic constraint on the acceptability of a sentence. We present results from two experiments. In the first experiment, we focus on the interaction of word order and context. In the second experiment, we investigate the additional effect of accent placement and clitic doubling. The results show that word order, in contrast to standard assumptions in the theoretical literature, plays only a secondary role in marking the Information Structure of a sentence. Order preferences are relatively weak and can be overridden by constraints on accent placement and clitic doubling. Our experiments also demonstrate that a null context shows the same preference pattern as an all focus context, indicating that 'default' word order and accent placement (in the absence of context) can be explained in terms of Information Structure. In the theoretical part of this paper, we formalize the interaction of syntactic and phonological constraints on Information Structure. We argue that this interaction is best captured using a notion of grammatical competition, such as the one developed by Optimality Theory (Prince & Smolensky, 1993. In particular, we exploit the optimality theoretic concept of constraint ranking to account for the fact that some constraint violations are more serious than others. We extend standard Optimality Theory to obtain a grammar model that predicts not only the optimal (i.e., grammatical) realization of a given input, but also makes predictions about the relative grammaticality of suboptimal structures. This allows us to derive a constraint hierarchy that accounts for the interaction of phonological and syntactic constraints on Information Structure and models the acceptability patterns found in the experimental data.PHONOLOGY COMPETES WITH SYNTAX 2