With the exception of the Philippines, America’s strategic interest in and engagement with Southeast Asia begins with World War II. Prior to that “Monsoon Asia” was remote and exotic—a place of fabled kingdoms, jungle headhunters, and tropical seas. By the end of the nineteenth century European powers had established colonial rule over the entire region except Thailand. Then, as the twentieth century dawned, the Spanish colonial holdings in the Philippines suddenly and unexpectedly became available to the United States as an outcome of the Spanish-American War and Admiral Dewey’s destruction of the decrepit Spanish fleet in Manila Bay. This chapter examines the strategic pivot in Southeast Asia and the role China plays in affecting the U.S. position in this region.