This profusely ornamented loving cup perfectly captures both the bravado and the political power of New York's Tammany Hall, a Democratic political machine that controlled party nominations and patronage from the mid-nineteenth century until 1932. The cup was presented to Tammany leader and state senator Thomas F. Grady (1853-1912) at a lavish banquet held on April 4, 1898, at the Hoffman House, a noted Broadway hotel. The cup is decorated with a profuse and eccentric array of Tammany symbols, not the least of which are the seventeen die-stamped portraits of Tammany "braves." The precise reason for Senator Grady's award is not recorded, but press coverage of the election of November 1897, in which Tammany Hall engineered a sweeping Democratic victory, suggests that the cup acknowledged Grady's efforts in securing municipal jobs for Tammany men-the "braves" depicted on the cup.