The smart city concept is widely accepted as the model for future cities to address the increasing challenges being caused by the growing population and limited city resources. Such a concept advocates the leveraging of existing infrastructure and developing technologies to push for authorities’ interconnectivity & coordinated efforts, and transparency & accessibility, with the intent of achieving city operational efficiency, which consequently, serves and enhances the quality of lives of the people. This paper looks at examining a variety of smart mobility initiatives undertaken by some of the leading smart cities of the world, analyze their resulting benefits, issues, and challenges encountered, and propose a mitigated-risk framework for such pursuit. A proposed framework is presented to illustrate the necessary short-term and longer-term deployment targets such as a series of minor infrastructure modifications followed by road network expansion. Association mining with CN2 Rule Induction Algorithm is applied to investigate the relationship of services especially mobility among lead smart cities and finding discussed. Also, expanding the internet coverage and reducing subscription costs from the technology side, followed by the adoption of emerging technologies to strengthen the smart mobility initiatives.