This cover cartoon reflects the results of a recent meeting between Democratic presidential nominee Grover Cleveland and representatives of the New York political machines of Senator David B. Hill and Tammany Hall. Dressed as dangerous bandits, Hill (left) and Tammany “Boss” Richard Croker (right) wink at each other in anticipation of the political spoils they will reap with a Cleveland victory. The candidate himself is shown short of stature and registering alarm with bulging eyes, sweaty brow, and leaping hat.
Hill and Tammany Hall had been Cleveland’s political enemies since the 1880s, and Tammany had backed Hill for the 1892 presidential nomination. After the Democratic National Convention, Croker endorsed Cleveland, but made it clear that he expected political favors in return. The nominee was worried that the machine politicians’ opposition would cause him to lose New York and the national election, but he was firmly set against making political deals with them. His campaign manager, William Whitney, insisted that some gesture of harmony on Cleveland’s part was necessary. When Whitney presented Cleveland with a conciliatory letter to sign, the candidate responded angrily, “I’ll see the whole outfit to the devil before I’ll do it.”
Whitney finally convinced a reluctant Cleveland to meet with members of the Hill and Tammany machines at the Victoria Hotel in New York City on September 8. Senator Hill refused to attend, as he had previously been absent from Cleveland’s official nomination notification and declined Whitney’s request to serve on the national ticket’s advisory committee. However, Hill’s state political machine was represented at the hotel by Lieutenant Governor William Sheehan and Democratic State Party chairman Edward Murphy.
The atmosphere at the conclave was tense, with Whitney supplying most of the conversation at dinner. Afterward, negotiations proceeded with frank talk from all. Sheehan and Murphy demanded specific commitments from Cleveland, but the nominee replied, “No promises,” and at one point threatened to withdraw from the race and publicly blame the New York political machines. Croker placated the candidate that he need not violate his integrity, but the Tammany boss also sought some assurance of future cooperation.
Whitney smoothed ruffled feathers and turned Cleveland’s vague statements into enough of a general pledge of sincere consideration for the political machines’ needs that those present agreed to aid the national ticket in the city and state of New York. Even the absent Hill later made brief campaign appearances for the cause, though without endorsing Cleveland by name. Of course Republican Judge interpreted the public harmony to mean that Hill and Tammany were now in charge of Cleveland.