This study is set out to present a syntactic analysis of ambiguous structures the headlines of political news reports in selected newspapers in Nigeria. The analysis aims at presenting what could be described as linguistic features of the ambiguous structures and as well determining the causes of the ambiguities. A total number of ten ambiguous structures taken from selected newspapers were analysed syntactically using the theory and sub theories of X-Bar syntax. An attempt is also made to categorize and characterise the ambiguities into types as revealed by the theory of syntax used. It was found out that most of the ambiguous structures were made ambiguous through the deletion or omission of certain sentential elements. The study concludes that, ambiguity, though a linguistic phenomenon, could be used deliberately and creatively by a writer as an instrument of humour and aesthetics in language use.