In the late 1890s, the United States was determining whether to annex Hawaii and other territories including Cuba, Puerto Rico, and the Philippines. American political cartoons often illustrated the concept of manifest destiny, or America's geopolitical expansion through colonization. Some cartoons would draw the United States as Uncle Sam and the territories considered for annexation as children, as if the United States was their warden. The children would often be drawn with dark skin and sometimes with grass skirts, nappy hair, or bare feet.

Historically, political cartoons expressed, shaped, reinforced, and reflected social, political, and racial attitudes and the sociopolitical structure of society. Therefore, some newspapers used cartoons as propaganda to shape public opinion. As mirrors to public knowledge, cartoons showed what the public did or did not know about events and scandals.