This study examines the relationship between wealth and the quality of life after age 65. Our results show that wealthier individuals use longer, healthier lives to work longer while retaining the longest work-free lives. Comparing cohorts turning 65 in 1996 and 2006, we show this inequality exacerbated over time. We then compare individuals’ subjective expectations of mortality, morbidity, and working after age 65 to our findings. Subjective views appear misaligned, especially for changes in the chances of death and work after age 65. In highlighting the growing disparity in longevity experiences, our findings challenge assumptions about Social Security program progressivity.