James Schoolcraft Sherman was an American politician who served as the 27th Vice President of United States under William Howard Taft’s administration. A member of the United States House of Representatives, Sherman was recognized as a powerful leader and skilled parliamentarian. His calm demeanour, sunny disposition, genial personality, and jovial spirit helped him sail through his political career with ease so much so that he earned the nickname, Sunny Jim. However, his congenial nature was not to be mistaken for his ineptness as he was a man with strong sense of character, firm beliefs and outright judgments. Sherman possessed a sense of stubbornness as well which kept him close to his principles, ideals and goals. During the Taft administration, Sherman’s old-guard conservativeness provided just the right amount of balance for Taft’s progressiveness in the Republican Party. He was lauded for his skilled approach and resilient tact. It was for this that Sherman became the only sitting Vice President to win re-nomination, after John C. Calhoun. However, his failing health did not allow him to contest as days before the parliamentary elections, he breathed his last.