Objective: To assess the role of unhealthy behaviors in the relationship between chronic stress and significant depressive symptoms by race/ethnicity among older adults. Method: Participant data from the 2006 to 2008 Health and Retirement Study were analyzed. Unhealthy behaviors included current smoking, excessive/binge drinking, and obesity. Chronic stress was defined by nine previously used factors. The eight-item Center for Epidemiologic Studies Depression (CES-D) Scale measured depressive symptoms, where ≥4 symptoms defined significant. Multivariable logistic regression assessed the effects of chronic stress and unhealthy behaviors in 2006 on depressive symptoms in 2008. Results: A higher chronic stress index score predicted depressive symptoms in 2008 among African Americans, Latinos, and Whites (adjusted odds ratio [aOR] = 1.78, 95% confidence interval [CI] = [1.48, 2.15]; aOR = 1.54, 95% CI = [1.15, 2.05]; and aOR = 1.40, 95% CI = [1.26, 1.56], respectively). Unhealthy behaviors moderated this relationship among Latinos (aOR = 1.54, 95% CI = [1.02, 2.33]). Discussion: Unhealthy behaviors were not effective coping mechanisms for chronic stress in terms of preventing significant depressive symptoms. Instead, they strengthened the relationship between chronic stress and significant depressive symptoms among Latinos.