Roosevelt, throughout his political life, felt that being prepared for conflict was the best recourse the United States had to prevent war. He believed that if the U.S. made a show of force to the rest of the world, other nations might be more hesitant to challenge the American military. As a corollary to this, he also understood that the threat of force rather than force itself was often sufficient to deter military conflict. He summarized this belief with an old African proverb, "Speak softly and carry a big stick, and you will go far." The press instantly latched onto this saying and used it to describe Roosevelt's style of foreign policy as Big Stick Diplomacy. Indeed, many of the political cartoons of the era depict the president swinging a large club to make others do as he wished.

Roosevelt brandished the Big Stick several times during his terms as president, most notably in Latin America. Various revolutions in the latter half of the 1800s had established many inefficient governments throughout Central America. In Venezuela, the newly self-proclaimed dictator, Castro, had conducted bad economic policies that drove the nation into poverty, leaving it unable to pay its European creditors. After a year of attempted negotiation, Germany attempted to force Venezuela into paying in 1902, blockading five ports on the coast of Venezuela and bombarding one of its coastal bases. Outraged, President Roosevelt threatened to attack the German ships if the siege on Venezuela continued. The Germans ceased fire and both Venezuela and Germany conducted successful negotiations. A year later in 1903, Roosevelt feared a similar situation and stepped in with a plan to help the impoverished government of Santo Domingo invest its money in order to pay its debts to Europe. Although the U.S. Senate rejected the plan, Roosevelt sidestepped the Senate with a temporary executive order to establish the investment funds. The plan worked, as the European nations were paid off and war was prevented in Santo Domingo.

Originally, President Roosevelt understood the grievances of the European powers who wished to collect on the debts owed to them in South America. He felt that the European nations could admonish the Latin American countries with any necessary means except occupation. Occupying a Latin American country would be a direct violation of the Monroe Doctrine issued almost a century earlier by U.S. President James Monroe. The Monroe Doctrine stipulated that all European powers should remain out of the Western Hemisphere. The Venezuela and Santo Domingo affairs changed Roosevelt's mind, however. To prevent the European powers from attempting any similar military actions and from gaining territory in Latin America, the president declared that only the United States had the right to correct the "wrong-doings" of the weaker states in the Western Hemisphere. This declaration came to be known as Roosevelt's Corollary to the Monroe Doctrine.

Roosevelt chose to prevent war in other ways as well. Twice during his Presidency he mediated disputes between aggressive foreign powers–in the name of promoting peace, but also secretly out of a desire to protect American interests in jeopardy. In 1905, Roosevelt offered to mediate the conflict between Russia and Japan, two nations that had been embroiled in a yearlong war over commercial rights in northern China and Korea. Roosevelt favored the Japanese but feared that American commercial interests in China would be jeopardized no matter which country won the war. Japanese and Russian delegates met with the president on board an U.S. Naval ship in Oyster Bay and later in Portsmouth, New Hampshire. Negotiations lasted three weeks. For his mediation efforts, President Roosevelt became the first American to receive the Nobel Peace Prize.

The Japanese were not entirely satisfied, however. Although the peace settlement had given Japan the southern half of Russia's Sakhalin Island, many Japanese felt this was insufficient tribute from Russia, who had technically lost the war. Anti-American sentiment began brewing in Japan and climaxed when rioters burned four churches in Tokyo. Many Americans, for their part, were not pleased with the Japanese either, somewhat resentful of the tide of Japanese immigrants that had been pouring into the country during the last decade. In 1906, the San Francisco Board of Education initiated a segregation policy and refused to admit Japanese students in the public school system. Japan was infuriated and the situation became more heated. President Roosevelt received several reports from other foreign intelligence agencies warning him that Japan was preparing for war. One report even mentioned that ten thousand Japanese troops disguised as laborers were waiting in Mexico to invade should war break out. Roosevelt understood the Japanese anger over the segregation policy in San Francisco and he had no desire for a conflict with Japan. Eventually an agreement was reached: San Francisco public schools readmitted the Japanese students, and Japan placed restrictions on the number of immigrants to the United States.

Within days of resolving the Russian-Japanese dispute, Roosevelt also mediated a conflict over the North African country of Morocco. In 1904 France and Great Britain signed a public treaty that granted France sole commercial rights in Morocco and Britain sole rights in Egypt, and that stipulated that Morocco would eventually be divided between the two. The German leader, Kaiser Wilhelm II, took this to be a threat to thwart German interests in Africa. War seemed likely to erupt. Having heard of Roosevelt's hand in designing the Open Door Policy in China, the Kaiser asked Roosevelt to mediate the dispute in Morocco, hoping the President would side with Germany. Fearing a war between the European powers and the disruption it would cause to American trade, Roosevelt agreed to mediate at the Algeciras Conference, but not in person. He sent a delegate, Henry White, to preside for him. Contrary to the Kaiser's hopes, Roosevelt upheld the treaty between England and France, leaving Germany with nothing. Years later, several historians interpreted Roosevelt's decision as the first step in aligning the United States with England and France against Germany in World War I.

Ironically, although Roosevelt acted as mediator in East Asia and in North Africa, he had trouble doing so in North America when Great Britain challenged the United States' claim to part of Alaska. Although many had previously considered Alaska a barren wasteland, the discovery of gold in the Klondike region in the late 1800s suddenly made Alaska a very popular and profitable territory, and many Americans rushed to the region during the Klondike Gold Rush. Great Britain, however, challenged the boundary line between Alaska and the British-owned Canadian province of British Columbia. This challenge outraged Roosevelt, who initially refused to negotiate the boundary line. He did eventually consent to arbitration by six impartial judges, three from the United States and three from Canada and Great Britain. Instead, however, Roosevelt sent three judges who were very partial to his interests: his Secretary of War Elihu Root, a former supportive Senator named George Turner, and Senator Henry Cabot Lodge who was arguably Roosevelt's closest and most trusted friend. These three convinced a judge from England to side with their pro-American viewpoint, and the United States won the dispute.

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