This study used the 2012 and 2014 panels of the Health and Retirement Study, a nationally representative dataset, to examine the associations between personality traits, generational cohorts, and bequest expectations among elderly households in the United States. The results indicated that neuroticism was associated with a lower subjective probability of leaving a bequest, and extroversion was associated with a higher subjective probability of leaving a bequest. Income, assets, and educational attainment were also positively associated with self‐reported bequest expectations. Generational differences were observed in the subjective probabilities of leaving bequests. The results of this study help in understanding the psychosocial factors associated with leaving bequests in an aging society, and provide implications for financial planners, practitioners, and policy makers.