The health of the people of Kentucky is of high concern for policymakers and citizens alike. Individuals want to live healthy, productive lives, while policymakers recognize that chronic illnesses cost the state in myriad ways. In this brief, we examine the link between educational attainment and health outcomes. We focus on two groups of health outcomes. The first are behavioral and include choices: tobacco use, alcohol use, obesity, and exercise. The second group are outcomes highly associated with these behaviors: heart attack, angina, stroke, and diabetes. The Center for Disease Control (CDC) estimates that these four diseases may cost Kentuckians over $5 billion annually in lost days at work and medical bills. Our simulations suggest that if Kentucky were to achieve education levels comparable to the U.S., we could reduce those costs by nearly $200 million per year.