After the conclusion of the War of 1898, there was uncertainty as to how Puerto Rico, the Philippines, Hawai‘i, and Guam would be incorporated in the United States. While some politicians were eager to establish trade routes through the new territories, others feared annexing lands inhabited by peoples of various races, languages, and cultures. Expansionists argued that the United States should carry the “white man’s burden” of educating others in “the art of self-government.” 

These prejudiced views are revealed in this cover issue of Harper’s Weekly. In this caricature, Uncle Sam is the only adult in a classroom, while the new territories are personified as children.