In this letter to Henry L. Sprague, a New York Republican ally, Theodore Roosevelt discusses an ongoing political contest over Louis F. Payn, the state’s Superintendent of Insurance. Roosevelt says he is encouraged by the apparent progress of the vote, although he remains cautious until the result is settled.

He explains that his approach has been to remain good-humoured and composed while refusing to compromise on his central demand: Payn, a Republican officeholder whose reappointment Roosevelt opposed, must leave, and any successor must be both upright and capable. Roosevelt contrasts this with the more aggressive tactics urged by some critics, arguing that bluster would have weakened his position. He illustrates his method with a West African proverb, “Speak softly and carry a big stick; you will go far.” In the letter, the phrase summarises a political strategy combining restraint, firmness and sufficient leverage to secure support.