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The purpose of this issue brief is to enhance understanding of the politics of health insurance coverage expansion efforts, thereby increasing the probabilities that such expansions may be achieved. This study looks at recent coverage expansion efforts in five large, demographically diverse states — California, New York, Pennsylvania, Massachusetts and Illinois. It examines a number of elements crucial to health reform, including: policy options; stakeholder analysis; electoral and partisan considerations; leadership; policymaking processes; and public opinion and involvement. Highly relevant, too, are environmental, systemic or governance rules that define the boundaries within which a policy initiative occurs and over which policymakers may have little or no control. Support for this project was provided by a grant from the Commonwealth Fund.