Abstract: Prior to the creation of the United Nations and even prior to Woodrow Wilson’s philosophy of intervention, members of Congress called for a humanitarian intervention to aid the people of Cuba as they fought against the violent oppression of the Spanish government. Spurred on by the first-hand accounts of horrifying atrocities, President William McKinley overcame his reluctance and called for the American military to aid the revolutionaries in Cuba. This initial decision marks the beginning of a very different path towards international dominance than the one created by European empires. Unlike their European counterparts, the United States would claim to use its military to protect those fighting for their freedom all over the world due to their longstanding commitment to the liberal ideal of self-determination. While it may appear benevolent, the United States struggled with questions about how a self-governing people could develop and use a large military to overthrow governments as well as whether these actions could be considered imperialism. Looking into this early effort to rid a country of violent oppression by offering military assistance provides a prism through which to view the ongoing struggles of liberalism that informs American foreign policy decision making.