Our research examined the impact of contextual intergroup variables on the subjective well-being of ethnic Russians in Estonia (N = 190) who have experienced major social changes with the demise of the Soviet Union. A mediational model was tested where aspects of intergroup relations (i.e., relative deprivation, status legitimization, and temporal comparisons) acted as mediators of the influence of cultural identity and representations of history on subjective well-being. Preliminary analyses indicated polemical representations of history in which Estonian historical narratives are established around the struggle for independence, and Russian representations of history are consolidated around victory in World War II. Mediation analyses demonstrated that the importance of Russian history increased the perceptions of relative deprivation, status delegitimization, and the frequency of temporal comparisons, which negatively affected life satisfaction. At the same time, the importance of Estonian history led to positive perceptions of the intergroup situation and, in turn, to greater subjective well-being. The effect of Russian identity on well-being was mediated by delegitimizing beliefs, but not by relative deprivation and temporal comparisons. Estonian identity did not exert a significant effect on the proposed mediators. The research demonstrates the salience of the effects of contextual intergroup factors on subjective well-being, and the article discusses implications for the study of intergroup relations and subjective well-being.