This article has investigated and contrasted the democratic values of two generations of university students in Taiwan separated by a decade (1991 and 2001). While the older generation began its political journey when Taiwan was at the critical turning point of making its change from authoritarianism to democracy, the younger generation came of political age when Taiwan was in the phase of habituating to democracy. The methodological issue addressed here is how we can properly assess and compare the two generations' democratic values in these dissimilar political contexts. In order to achieve equivalent measurement across the two generations, item response theory (IRT) was used to measure democratic values of the two generations. Contrary to what existing literature would predict, the results show that the older generation's democratic values are higher than those of the younger generation. This unexpected lowered level of democratic values was then accounted for by examining the varied political contexts in which the two generations grew up.