Eliminating disparities in health and health care is a long-standing objective of the US government. Racial and ethnic differences in insurance coverage pose a major obstacle to achieving this objective. With important coverage provisions of the Affordable Care Act beginning to take effect, we propose a new way of conceptualizing and quantifying the racial and ethnic disadvantages of uninsurance over the course of a lifetime. Using a life expectancy approach, we estimate the number of years whites, blacks, and Hispanics can expect to live in insurance “double jeopardy”: being uninsured while also in lesser health and, therefore, at higher risk of needing medical care. Our measures indicate that compared to whites, Hispanics and blacks are more likely not only to be uninsured at any point throughout most of their lives, but also to spend more years uninsured and spend more of these uninsured years at high risk of needing medical care. These life expectancy measures—designed for ease of use by policy makers, researchers, and the general public—have the potential to reframe the discussion of disparities and monitor progress toward their elimination.