Abstract: There is an increasing interest in the question as to which aspects in speech are tightly coupled with co-speech gesture. A general consensus now exists that gestural representation is influenced by event structure, but it is less clear to what extent gesture interacts with syntactic encoding. The present study thus investigates the issue, taking the double object construction and its prepositional paraphrase (both expressing transfer events) in relation to gesture as the starting point. Based on data from American English talk show programs, it is found that the rate of gesture production is closely linked with the event structure, whereas gestural Modes of Representation and the dynamicity of Acting gestures are clearly sensitive to the subjective online conceptualization of events or syntactic constructions in encoding events in addition to the event structure. The current findings constitute further evidence in supporting the hypothesis which predicts that gestural representation is determined by the online choice of the syntactic encoding/the online construal of events as well as non-linguistic motor-spatial properties of events, but they are at odds with the Free Imagery Hypothesis, which predicts that gestural representation simply derives from pre-linguistic imagery.