During the Gilded Age, the Vanderbilts became one of the wealthiest families in the world. Yet within New York City society, simply having a fortune wasn’t enough to be accepted by the fellow wealthy families of the upper echelon.

The Vanderbilts had money, billions of it by today’s standards, but it was new money — and that wasn’t enough to impress the old guard or its leading doyenne, Caroline Schermerhorn Astor . Together with fellow society arbiter Ward McAllister , she developed the notorious 400 List, an exclusive index of New York City’s social elite several Vanderbilts yearned to be a part of.

Social acceptance, then, required not just…

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