Instead of rum and Caribbean beaches the U.S. purchased what territory from the Russian Empire in 1867? It was known as “Seward's Folly” until gold and oil were found.

Coal stations in the Pacific were important because in 1854 the U.S. opened what country via a flotilla of ships led by Matthew Perry?

Which collection of Islands were annexed by the U.S. in 1898 due to economic / military reasons as it was home to many U.S. sugar plantations and the U.S. Pacific fleet?

What conflict lead to the U.S. gaining many overseas territories in the late 19th century?

What event was the catalyst for the U.S. entry in to the Spanish American War?

This individual gave up his government post to participate in the Spanish American War, famously charging up San Juan Hill with his rough riders.

What new territories did the U.S. gain from Spain after the Spanish American War?

The Spanish American War / Platt Amendment gave the U.S. a permanent lease on what in Cuba?

As part of a growing international presence the U.S. participated in what international affair in China?

Inhabitants of which newly annexed territory fought a bloody war for independence against the Americans over four years?

Which set of Supreme Court cases between 1901-1904 largely determined the legal status of annexed territories which were possessions of the U.S.?

Which progressive American President is known for the following phrase which was about projecting power, “Speak Softly, but carry a big stick.”?

Which progressive American President is known for Dollar Diplomacy?

Which progressive American President came from the world academia having been the President of Princeton and is known for “Moral Diplomacy” and later his involvement in the peace negotiations following WWI?