||The purpose of this thesis is to provide a comparative study of American public education strategies in two of its colonial possessions at the beginning of the 20th century. The United States defeated the Spanish in 1899 and took over the Philippines and Puerto Rico, both of which shared a long history of Spanish rule. Victory in the war with Spain propelled the United States into the ranks of the imperial club and posed challenges greater than any encountered in the conquest of the native Americans and the West. At the time of Spain's defeat Filipinos had already taken up arms against the Spanish while Puerto Ricans had won concessions through negotiation and both looked forward to independence; however, the U.S. intention to retain lands that they felt had been won fairly in battle dashed such hopes. Before President McKinley could apply American-style, liberal, republican governance to what he and most Anglo-Saxons viewed as the less civilized natives of these territories, the army had to quell an armed Filipino resistance and lay the groundwork for a colonial government. Offering free public education became a key component of a U.S. strategy to create compliant citizens and at the same time shrink the ranks of those willing to take up arms against American rule. American attempts to expand the availability of education in the Philippines, scene of some of the most ferocious fighting, have received a lot of praise mainly for its nobility and accomplishments. However, judging the effort based upon the original goal of creating an educated populace capable of taking its leaders to task reveals shortcomings. This thesis compares American public education in the Philippines with the system implemented in Puerto Rico. It has been over a century since Admiral Dewey entered Manila Bay, but a study of the strategies used in the American territories can still provide lessons today. Nations, including the U.S., continue to invade other countries for various reasons, stated and otherwise. Invariably, some form of rebuilding occurs after an invasion and are presented as concise steps leading to a preferred outcome. Looking back at early American imperialism in the Philippines and Puerto Rico provides evidence that plans, even those that are the centerpiece of a strategy, remain very malleable- pushed, pulled and sometimes broken due to the exertions of those who claim an interest or instead may be threatened. The influence of native leaders, colonial administrators, U.S. politicians, and corporations all played a part in determining the successes and failures of the imperial enterprise.