This book seeks to understand the politics of deservingness for future Social Security reforms through an interpretive policy analysis of the 2005 Social Security privatization debates. What does it mean for politics and policymaking that Social Security recipients are widely viewed as deserving of the benefits they receive? In the 2005 privatization debates, Congress framed Social Security in exclusively positive terms, often in opposition to welfare, and imagined their own beloved family members as recipients. Advocates for private accounts sought to navigate the politics of deservingness by dividing the “we” of social insurance to a “me” of private investment and a “them” of individual rate of return in order to justify the introduction of private accounts into Social Security. Fiscal stress on the program will likely bring Social Security to the policy agenda soon. Understanding the politics of deservingness will be central to navigating those debates.