This paper compares mortality between Gold and Silver medalists in Olympic Track and Field to study how achievement influences health. Contrary to conventional wisdom, winners die over one year earlier than losers. I find strong evidence of differences in earnings and occupational choices as a mechanism. Losers pursued higher-paying occupations than winners according to individual Census records. I find no evidence consistent with selection or risk-taking. How people respond to success or failure in pivotal life events may produce long-lasting consequences for health.