Inside high society's most brutal rules: how the Astor family dictated America's Gilded Age elite

The Gilded Age, which arose between the American Civil War (1861-1865) and the turn of the 20th century, is a period defined by a stratospheric explosion of wealth that introduced the world to America's very first multi-millionaire: John Jacob Astor.

The era was defined by the unique society that lived it — and commandeered it. They were completely bound to stringent rules that dictated not only their place in society (whether they were part of this exclusive upper echelon or not) but also how to behave in it.

Such rules and who made up the group itself, the famous 400 index, were largely decreed by John Jacob's granddaughter-in-law, society doyenne Caroline Schermerhorn Astor, a descendant of New York City's original Dutch settlers, ergo definitionally "old money."

Who was Caroline Astor?

Caroline was born on September 22, 1830, into a wealthy family who were part of New York City's Dutch aristocracy and made their money in shipping. In 1853, one day after her 23rd birthday, she married William Backhouse Astor Jr. (1829-1892), son of real estate businessman William Backhouse Astor Sr. and grandson of world's first millionaire John Jacob.

Though today the Astors are known as one of the quintessential old money families of the Gilded Age, and they certainly were, Caroline's pedigree was superior. She was a member of a true Knickerbocker family, the name given to New York residents with close, direct lineage to the Dutch settlers of the 1600s.

The penchant for societal gatekeeping Caroline has become known for today didn't always define her; she became a champion of old money, proper etiquette and tradition in the years after the Civil War, when New York City's population grew exponentially, between immigrants, arrivistes and "Swells," as the nouveau riche of the Gilded Age were referred to.

These groups began challenging the dominance of the old New York Establishment, and together with fellow social arbiter Ward McAllister, Caroline set about establishing just who truly belonged in Fashionable Society — and how they ought to behave.

Who was Ward McAllister?

McAllister was born in 1827 to a prominent judicial family in Savannah, Georgia. In the years before becoming the ultimate tastemaker of New York City society, he traveled throughout European cities and spa towns, where he picked up on the mannerisms of other wealthy Americans and titled nobility, and forged his desire to be a member and potentate of Gilded Age society.

He was the one to coin the phrase The Four Hundred (he allegedly arrived on the number because it was the amount of people that fit in Mrs. Astor's ballroom at her Beechwood estate in Newport, Rhode Island), claiming that there were only 400 people worthy for New York Society. McAllister published an official list of "the Only Four Hundred" in the New York Times on February 16, 1892.

In 1890, McAllister had memorialized The 400, along with more of his and Mrs. Astor's rules, in his memoir Society as I Have Found It; however, the book also brought on his downfall. High society — the old guard, who valued discretion, specifically — were turned off by the tell-all, and he was eventually ostracized from the society he famously gatekept. He died while dining alone at New York's Union Club in 1895.

The Rules

The three-generation rule

Money alone was far from sufficient to qualify as a member of the upper echelon, who absolutely scoffed and turned their backs on the nouveau riche (until they themselves had their backs up against the wall). Old lineage was essential, and for a family to be considered part of the high society index, their money had to be separated from its current earner by at least three generations.

A certain liquid threshold

But lineage alone wasn't enough either. McAllister famously noted that families needed at least $1 million (roughly $30 million today) in liquid capital to properly partake in Gilded Age society by entertaining and maintaining a social presence. "A fortune of a million dollars is only respectable poverty," he is said to have said.

The calling card system

Mrs. Astor was effectively a bouncer for high society, and to further cement her role, her peers strictly followed the calling card system, especially amid the influx of "Swells," who had all the money in their world to make themselves the upper class' neighbors. Polite society did not recognize a family's existence, and newcomers couldn't interact with or invite them, if the reigning matriarch of the household had not personally dropped off a calling card at their residence. 

The system came to a head after the Vanderbilts moved up to Fifth Avenue. In 1883, Alva Vanderbilt and her husband William Kissam Vanderbilt had just moved into their new French-château-style mansion at 660 Fifth Avenue, where Alva was planning on hosting her Fancy Dress Ball, inviting 1,200 for it (and spending millions in today's currency on it).

Mrs. Astor's youngest daughter Carrie was part of youth rehearsals for the choreographed dances that would take place at the ball, but when invitations were sent out, neither she nor her mother received one. Alva, in a brilliantly clever tactical maneuver, outsmarting "The Rules," claimed she could not invite Carrie, as her mother had never dropped off a calling card for the family.

Mrs. Astor was left with two options: enforce the society rules and devastate her daughter, or surrender to the new (money) guard. She ultimately accepted the invitation, officially sanctioning the Vanderbilt family into the highest tier of New York society.

New money's ultimate coup

The stand-off between Mrs. Astor and Alva was merely a pre-game for the ultimate stand-off between old and new money as a whole: The "Opera War" of 1883. Another notable event for the "ton" was outings to the opera, held at The Academy of Music. However, the city's premier opera venue had only 18 private boxes, of course all owned by old money, who effectively shut out new money from the best seats in the house. 

The excluded families, with their new, soaring fortunes and led by the Vanderbilts, instead funded and built the Metropolitan Opera House, which dwarfed the Academy. Both opera houses launched their season on the same night in October, forcing society to pick a side, with the Metropolitan Opera ultimately prevailing. The old guard migrated to the newer opera house, and the Academy stopped hosting opera in 1886.

The end of the social war

The new money party may have been excluded for years, but they were unrelenting; they had the money to render old money traditions and institutions obsolete, like the Academy of Music, and make new ones that both new and old money were a part of, like the Metropolitan Opera.

By the late 1890s and turn of the century, after the slow but steady acquiescence of the old guard, the two camps eventually dissolved into a unified ruling class through institutional consolidation as well as strategic marriages. They also had a new common enemy: The Progressive Era, which kicked off in the 1890s and boomed in the early 1900s, amid economic panics. Rising labor strikes and income tax proposals forced the ultra-wealthy to stop fighting each other, and focus on protecting their collective corporate and class interests.

The Astors remained a prominent, wealthy family until 1959, when Vincent Astor died, though his widow Brooke Astor also continued living lavishly and as a New York City socialite until her death in 2007, when she was 105. The Vanderbilts meanwhile lost much of their fortune four generations after Cornelius "The Commodore" Vanderbilt first earned it, though their legacy is carried on through Gloria Vanderbilt's son, renowned CNN journalist Anderson Cooper.

It was New York City itself, in a way, that was the ultimate winner however, solidifying itself as a global cultural capital. The old and new money clash and their competitive philanthropy endowed some of the city's most iconic institutions: The Metropolitan Opera of course, as well as The Metropolitan Museum of Art, The Whitney Museum of American Art, The New York Public Library, Trinity Church, and Temple Emanu-El.