Nineteenth century America was in social and political transition. Urban centers on the East Coast overflowed with European immigrants and rural transplants, and political systems readjusted to address the issues raised by this new population. At the same time, clubs and fraternal organization offered a social infrastructure within the cities. Baseball emerged as an important pastime in these times of change, and the urban political machine, exemplified by Boss Tweed of New York Tammany Hall, used the new game as way to control the teeming masses. In fact, to make sure he could maintain his influence with regard to this new social phenomenon, Tweed placed all the members of the New York Mutuals amateur baseball club on the City’s payroll in the sanitation department in violation of all existing rules for regulating the game in the 1860s. This article, a chapter from the forthcoming book, THE WORLD OF SPORTS AND POLITICS, demonstrates the synergistic relationship between American urban government and the business of sports.