Taiwan's purchase of weaponry from the United States has been an intriguing question to scholars and practitioners in Taiwan as well as the United States. To date, despite the growing threat put forth by mainland China's military strength, the question of why Taiwan is somehow short of actions as revealed in its delay in defense procurement is still under contestation. This paper employs the neoclassical realist approach to explain why there seems to be a gap in practice between the U.S. "goodwill" to sell and Taiwan's seemingly delayed response under the Chen administration. In addition, the author further investigates Taiwan's considerations under the Ma administration. The author argues that this gap can be attributed to the thinking of political elites in Taiwan, such as their perceptions of China's resolve and capabilities to unify Taiwan and of U.S. determination to protect Taiwan, their political considerations that aim to prevent the rivals from gaining domestic and international support, and their views about the most cost-effective ways to allocate national financial resources. With the review of relevant debates in Taiwan between 2000 and 2012, the preliminary findings of this paper indicate that political elites have become more pragmatic in terms of perceptions of mainland China and of the U.S., and yet partisanship and resource allocation seem to dominate, if not determine, their views on U.S. arms sales to Taiwan.