It is well established that the United States lags behind peer nations in life expectancy, but it is less established that there is heterogeneity in life expectancy trends. We compared mortality trends from 2004 to 2014 for the United States with 17 high-income countries for persons under and over 65. The United States ranked last in survival gains for the young but ranked near the middle for persons over 65, the group with universal access to public insurance. To explore the over-65 mortality trend, we estimated Cox proportional hazards models for individuals soon after entering Medicare. These were estimated separately by race and sex, controlling for 26 chronic conditions and condition-specific time trends. The separate regressions enabled survival comparisons for the 2004 and 2014 cohorts by race and sex, conditional on baseline health. We predicted 5-year survival for all combinations of diabetes, hyperlipidemia, hypertension, and ischemic heart disease (IHD). All 16 combinations of these conditions showed survival gains, with diabetes as a key driver. Notably, survival improved and racial disparities narrowed for individuals with diabetes, hypertension, and IHD. White females, black females, white males, and black males gained 3.61, 3.90, 3.57, and 5.89 percentage points in 5-year survival, respectively.