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The central aim of this study is to examine and highlight the role of local government in community development. Drawing evidence from Iwo Local Government Area of Osun State, Nigeria, this study brings the Nigerian political arrangement to the fore by establishing its negation of the undergrowth of community development which underscores true federalism. Relying on the General Systems theory further, this study established a linkage between local government and community development in Nigeria. Challenges such as lack of true federalism, local government autonomy, lack of funds, and under-staffing were discovered as root causes of local governments' inability and failure to initiate and consolidate community development in Nigeria. A multi-pronged approach adequately founded on true federalism should be adopted by the government to addressing these identified challenges with a view to re-positioning local governments in Nigeria on the path of community development, and national development.