 A Tammany Hall Democrat, he began his political career as a city alderman from 1883–1884, where he was one of only two aldermen not caught up in a financial scandal related to the Broadway Surface Railroad.For the remainder of his public career, however, he was a compliant member of Tammany under the patronage and control of its leader Richard Croker.Grant lost the race for mayor as Tammany's candidate in 1885, but won the office of sheriff in 1886.