While Teddy Roosevelt was progressive domestically and didn't have many personal failings (he was a dedicated family man), it can be argued that his imperialist policies hurt other countries and set a poor precedent for American foreign policy. For example, when he was Assistant Secretary of the Navy, he agitated for the U.S. to become involved in the conflict between Cuba and Spain as Cuba was fighting for independence from Spain. When the Secretary of...
While Teddy Roosevelt was progressive domestically and didn't have many personal failings (he was a dedicated family man), it can be argued that his imperialist policies hurt other countries and set a poor precedent for American foreign policy. For example, when he was Assistant Secretary of the Navy, he agitated for the U.S. to become involved in the conflict between Cuba and Spain as Cuba was fighting for independence from Spain. When the Secretary of the Navy was away, the U.S. battleship the Maine exploded in Havana harbor, and Roosevelt informed the navy that they should prepare for war. He was clearly itching for a fight, and he played a critical role in dragging the U.S. into the Spanish-American War. In the war, he fought at San Juan Hill in Cuba as part of the Rough Riders. He asked the Rough Riders to charge up San Juan Hill, without any orders from superiors, and 200 soldiers were killed and 1,000 soldiers were injured as a result. In addition, as a fervent imperialist, he also pushed for American control of the Philippines, which were subdued with a great deal of American military aggression and subjugation of the Filipino people.
As President, he continued his imperialist policies. For example, he wanted an isthmus canal to be built in Central American to reduce the time it took for ships to travel from the Atlantic to the Pacific Coast (or to make the reverse journey). When Columbia refused to allow a canal to be built in their country, he supported a revolt in Panama that enabled an American-controlled canal to be built there.
One other thing you can use against Teddy Roosevelt is his behavior during the Panic of 1907. He allowed J.P. Morgan's U.S. Steel to inject money into a failing railroad, coal, and iron company to prop it up, and this action went against his position as an anti-monopolist.
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