Though City Hall and the County Courthouse remained down, during the late 19th and early 20th centuries, much of New York City’s political power, vested in its wealthiest individuals, moved uptown. From the first waves of famine-fleeing Irish in the 1840s, to the flocks of Italians, Eastern Europeans, Germans, Jews, and more that would immigrate during the next 75 years, Manhattan’s Lower East Side became one of the most robust (and populous) immigrant communities in the entire world. However, as streams of often-poor immigrants settled in the very place where New York City was born–Dutch New Amsterdam–the city’s established elite, led by Gilded Age nouveau riche, began to clamor for new abodes. As the 19th century rolled into the 20th, well-to-do families, including the Vanderbilts, Roosevelts, Carnegies, Fricks, Beeckmans, and Davisons, climbed 5th Avenue, with many of them eventually settling in the neighborhood known as Lenox Hill. The Lenox Hill neighborhood can be considered as the streets between 59th and 77th, bounded by 5th Ave. and Lexington. While during the Gilded Age (roughly 1865 to 1914) New Yorkers could utilize street numbers to delineate neighborhoods, the initiative that led to this method of organization also foreshadowed some of the economic and political force that would later be found in uptown enclaves like Lenox Hill. The 1811 Commissioner’s Plan for Manhattan’s rectilinear grid established both the logistical layout of the city’s streets and predicted the economic value those streets would create. Though planners Gouverneur Morris, Simeon De Witt, and John Rutherfurd proposed that uptown streets would provide river-to-river trade corridors and that centralized markets would become an essential facet of Manhattan’s economic design, their most significant judgment on the island was of its land’s value being “uncommonly great.” Recognizing the Commissioners’ evaluation of Manhattan as a project in wealth-building, historians can see how uptown neighborhoods with concentrations of capital, such as Lenox Hill, later fit so naturally into the city’s Gilded-Age growth. To understand Gilded-Age Lenox Hill as a community of wealth and political power, historians may consider the mansions of affluent families like the Livingstons, Beeckmans, Roosevelts, Fricks, and Davisons. Additionally, they may analyze the history of how those families came to Lenox Hill, the sites where these families convened to take advantage of their shared political influence, and their connections to the political establishment of the modern day. Due to its high economic barrier to entry, the Lenox Hill nouveau riche community of the Gilded Age provided members a site to concentrate political power and further social ties.