The cartoon shows Roosevelt as an octupus with his different involvements in national affairs as thetentacles. Under Roosevelt's administration, the U.S. became a major imperialistic power. This is shown in Rosevelt's big stick policy, in which he often threatened other countries with military intereference. Also showing Roosevelt's imperialism was the Roosevelt's corrolary, which modified the Monroe Doctrine to protect the U.S.'s new territorial holdings in Latin America and the Carribean. Roosevelt was also involved in the dispute between Russia and Japan, which he mediated with the Portsmouth Conference. The Root-Takahira agreement between Japan and the U.S. consisted of the promise of both countries to respect the other's territorial holdings.
The cartoon shows the eagerness of countries such as Russia, Germany, and America to become involved in the Chinese economy following it's defeat by Japan. The Open Door policy was established in 1899 by Secretary of State John Hay. It declared respect for Chinese rights and fair competition. This policy was not well received by patriotic Chinese. As a result, the Boxer rebellion broke out in 1900 and led to the deaths of two hundred foreigners and thousands of Chinese Christians. The Treaty of Wanghia allowed the U.S. to send American troops to quell the rebellion and to ensure keep the Open Door policy in tact.
The cartoon shows the situation between America and Puerto Rico after the Foraker Act was passed in 1900. The act gave Puerto Ricans a small amount of popular government. Though Congress gave Puerto Ricans U.S. citizenship, they were not given full American rights. This was shown in the Insular Cases, in which the Supreme Court denied Puerto Ricans full American rights.