Littlefield was a politically active individual but never sought office himself. Himself a teetotaler, he opposed prohibition. He gave and bequeathed some $3 million to UT — more than any other individual during the first fifty years of the existence of the university. Littlefield's gifts preceded the larger ones which came later from numerous oil philanthropists. By virtue of his philanthropy, Littlefield's name is visibly entwined with many aspects of UT life. He believed that the UT textbooks were too Northern-focused; so in 1914, he established the "Littlefield Fund for Southern History" to amass the archival sources which the historian Eugene C. Barker told him were needed to obtain a more accurate writing of history. Many Southern-themed books in circulation at university libraries today are stamped with Littlefield's name as a result. In 1917, when Governor James E. Ferguson vetoed appropriations for UT in the state budget, Littlefield offered to fund its operations for the biennial period from his personal funds.