In 1868, he formed J.S. Kennedy & Company, a banking firm, and spent the next fifteen years devoting himself to "financial affairs of magnitude and importance." He aided in the reorganization of various financial concerns, notably in 1888, when he acted with J. S. Harris as receiver of the New Jersey Central Railroad, and served as president of the International & Great Northern Railroad Company of Texas as well as a director, and vice-president, of the Indianapolis, Cincinnati and Lafayette Railroad Company of which he helped reorganize after its 1870 bankruptcy.