Returning home, Stephens entered the Central National Bank of Boonville, managed by his father, and became director, assistant cashier and vice president. During his connection with this institution he and his brother, W. Speed Stephens, funded the debts of various counties in central Missouri. Stephens was also involved in politics, acting as an aide-de-camp on the staff of Governor John Marmaduke. In 1887, at the age of twenty-nine, he was appointed by the comptroller of the currency as receiver of the Fifth National Bank, of St. Louis. Its affairs were convoluted, and experienced financiers doubted the ability of so young a man to master so difficult a task. He succeeded in closing up the affairs of the bank in a brief time, the depositors receiving 96 per cent upon their accounts, when only 33 1–3 per cent was expected, and the achievement at once gave him high standing in financial circles.