Emphasizing the intersection of policy and politics, this paper uses Theda Skocpol's polity-centered approach (1992) to analyze two key moments in the history of the 21st Century Community Learning Centers (CCLC) program: (1) 1998, when the program's budget grew from $40 million to $200 million; and (2) 2003, when President Bush attempted to cut the program's budget from $1 billion to $400 million. A thorough understanding of this history can help afterschool advocates successfully respond to President Obama's recent proposal to dramatically change the 21st CCLC program once again. This paper uses Skocpol's polity-centered approach to explain why efforts to change the 21st CCLC program were successful in 1998 and unsuccessful in 2003. It explores the way that changing work patterns and growing interest in positive youth development helped create broad support for afterschool during the 1990s. This paper pays particular attention to the congruence among the interests and abilities of philanthropists, U.S. Department of Education (US DOE) leaders, and the White House during the late 1990s, as well as between Congressional leaders and afterschool advocates during 2003. It discusses changes to the balance of power between the Democrats and Republicans during both time periods and explores the way that the expansion of the 21st CCLC program in 1998, and subsequent changes, worked to frustrate the President's efforts in 2003. This paper concludes by reviewing recent controversy surrounding President Obama's proposed changes to the 21st CCLC program, suggesting that afterschool advocates consider the President's efforts in light of history, and draw on the past to shape their response.