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Anti-imperialism has transformed throughout several phases, each with distinct social, economic, and political motivations and objectives. Attempts to annex countries like Santo Domingo and Cuba failed in the U.S. Congress from the 1850s through the 1870s, largely due to very conservative politics. It was not until the aftermath of the Spanish-American War, when the Anti-Imperialist League became part of the progressive movement, that anti-imperialism became a social cause. Finally, later in the 20th century, antiimperialists objected to U.S. expansion and military involvement in places such as Vietnam, Central America, and the Middle East.

In its first phase, which is ideologically and tactically very different from the second and third, antiimperialist sentiment in the United States consisted mainly of congressional representatives who opposed the annexation of territories in the Caribbean, South Pacific, and Mexico. In large part, the slavery debate influenced the congressional refusal to annex overseas territories; annexation would not only alter the balance of free and slave states but also usher thousands to millions of new citizens into the body politic. The racial background of these potential citizens, who were overwhelmingly non-European, proved a deterrent against the annexation of their homelands because racist ideology and political rhetoric claimed they were not capable of self-government and not civilized. Ulysses S. Grant's 1870 plan to annex Santo Domingo and make it a refuge for former slaves illustrates some of the complicated racial politics of imperialism. While, prior to 1900, many political anti-imperialists believed that islands like Santo Domingo, Cuba, and Hawai'i were inhabited by “primitive” cultures and thus unappealing and possibly a contaminant to the Anglo-American polity, an equally racist mix of missionary impulses and the desire to remove former slaves from the U.S. mainland informed imperial ventures.

By 1900, anti-imperialism was associated with the progressive movement and informed by an anti-racist agenda. This second phase of anti-imperialism, that turned anti-imperialism into a social movement, began after the Spanish-American War. When Cuba, Puerto Rico, and the Philippines came under U.S. control, numerous factions continued to debate the status of these new territories, and their subjects, within the body politic. President William McKinley engaged the United States in a war with Philippine nationalists after the United States defeated Spanish forces in the Philippines. In November 1898, a group of prominent Boston citizens organized the Anti-Imperialist League. Within a year, their ranks had soared to more than 30,000 members. The highly controversial war with the Philippines, which McKinley insisted was the only alternative to even more bloodshed among Philippine nationals, the Spanish, and Japanese, brought McKinley much criticism and centered the Philippines on the Anti-Imperialist League's agenda.

The Anti-Imperialist League's leaders included Chicago reformer Jane Addams, the steel magnate Andrew Carnegie, Samuel Gompers of the American Federation of Labor, and Moorfield Storey, a prominent Boston lawyer who later became the first president of the National Association for the Advancement of Colored People (NAACP). Other members included W. E. B. Du Bois and James Weldon Johnson, who would become prominent figures in the NAACP. The ranks of the Anti-Imperialist League also included suffragists and former abolitionists such as Mary Livermore and Oswald Garrison Villard.

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