This paper develops a model of cross-Strait relations in terms of a series of four paradoxes. The first is that China’s aggressiveness in initiating the Taiwan Strait Crisis of 1995-96 set off a series of contretemps between the two sides of the Strait that almost certainly made the achievement of Beijing’s objectives considerably harder. Second, the polarization in Taiwan over national identity and cross-Strait relations that erupted after the turn of the century was at least somewhat surprising, both because the partisan cleavage on these issues had noticeably de-escalated during the 1990s and because public opinion on them has always been decidedly unpolarized. Third, despite strident DPP criticism that Ma Ying-jeou, the current KMT President, has threatened Taiwan by increasing its economic dependency upon the PRC, the huge surge in Taiwan’s trade and investment with China this century actually occurred during the administration of his DPP predecessor, Chen Shui-bian. Fourth, the rapprochement between Taiwan and China after Ma’s election in 2008 is at least somewhat paradoxical because it may not presage long-term stability in cross-Strait relations. Ma’s reluctance to enter into political negotiations with the PRC indicates that he agrees with the DPP to some extent about the danger of falling into China’s clutches (even if this belies their charges about his motivations); and the PRC’s refusal to make any concessions about Taiwan’s sovereignty suggests that future conflict might be likely.