The Gilded Age is not known for its presidents. The chief executives from 1876 to 1896 saw themselves not as active leaders but as checks against, or in some cases enablers of, a corrupt Congress; this “light touch” leadership condemned most of them to obscurity beyond political history nerds. One exception is Grover Cleveland, America’s first nonconsecutive president. Gilded Age Democrats loved Cleveland during his first term for his fiscal responsibility; they also turned against him during his second term for the same reason. This culminated in the Democrats backing a presidential candidate who was the opposite of Cleveland. If we are to understand the party’s turning on Cleveland, we must examine his life.