My thesis examines annexation disputes from the mid-1800s to the present in Pittsburgh. My particular focus is on the clashes between the cities of Pittsburgh and Allegheny. I look at why Pittsburgh’s annexation of Allegheny in 1906 succeeded while previous attempts to annex Allegheny failed. A combination of better lawyering and a unified elite class enabled Pittsburgh to finally annex Allegheny. The U.S. Supreme Court made this annexation official through the 1907 case of Hunter v. City of Pittsburgh. This case has a rich history and legacy. Much can be gleaned about the broader Progressive Era by examining this case in conjunction with the annexation. I conclude that the case and the annexation reflected a drive for efficiency then sweeping the elites of the nation. In addition, I assert that both the annexation and the Hunter decision highlighted the power of elites at this time to accomplish their goals.