Depression, stress, and poor sleep have been associated with increased pain among older adults; positive resources, such as resilience and social networks, may help to buffer the impacts of these negative attributes on pain outcomes. The primary objective was to determine the relative effects of positive resources and negative attributes on pain outcomes among older adults with diagnosed back pain, osteoarthritis, and rheumatoid arthritis. The stratified study sample was identified from older adults ages ≥65 years. Members received a survey assessing positive resources (resilience, social networks), negative attributes (depression, stress, poor sleep), and pain outcomes (severity, interference). Opioid and other medication use was determined from pharmaceutical claims. After weighting to representative distributions of pain conditions and adjusting for survey response bias, multinomial logistic regressions were used to determine the relative associations of positive and negative attributes on pain outcomes. Among survey respondents (N = 4161), prevalence of self-reported pain severity and interference for no/mild, moderate, and severe categories was 61%, 21%, and 18%, and 67%, 16%, and 17%, respectively. In bivariate models, negative attributes of depression, stress, and poor sleep had stronger associations with pain severity and interference than the moderating effects of positive resources of high resilience and diverse social networks. In fully adjusted multivariate models, the strongest associations with moderate and severe pain severity and interference remained depression, stress, and poor sleep. Based on these results, multidimensional pain management strategies should include management of negative attributes along with enhancement of positive resources for effective management of chronic pain.