Since its inception in 1986, Taiwan's main opposition party, the Democratic Progressive Party (DPP), has struggled to establish itself as a competitor for national political power. The victory of DPP candidate Chen Shui-bian in the 2000 presidential election marked a major breakthrough, not only for the DPP, but for Taiwan's young democracy as well. This article examines the party's history with an eye to explaining both its extended failure to win national office and its eventual success. The paper identifies two sets of factors: aspects of Taiwan's political system that worked to the advantage of the ruling KMT and historical errors committed by the DPP. It then shows how the KMT's advantages degraded in 2000, just as the DPP overcame its self-imposed liabilities, resulting in a DPP presidency.