Parse-tree paths are commonly used to incorporate information from syntactic parses into NLP systems. These systems typically treat the paths as atomic (or nearly atomic) features; these features are quite sparse due to the immense variety of syntactic expression. In this paper, we propose a general method for learning how to iteratively simplify a sentence, thus decomposing complicated syntax into small, easy-to-process pieces. Our method applies a series of hand-written transformation rules corresponding to basic syntactic patterns -for example, one rule "depassivizes" a sentence. The model is parameterized by learned weights specifying preferences for some rules over others. After applying all possible transformations to a sentence, we are left with a set of candidate simplified sentences. We apply our simplification system to semantic role labeling (SRL). As we do not have labeled examples of correct simplifications, we use labeled training data for the SRL task to joint...