The richest of the old-money families of the Upper East Side had made the bulk of their fortunes during the industrial boom that began in the middle of the nineteenth century. Typically of Anglo-Saxon descent, many could trace their ancestry back to colonial times. Socially clannish, snobbish, and elitist, the ultrawealthy were also responsible for financing many of Manhattan's cultural landmarks, such as Rockefeller Center, Carnegie Hall, and Grand Central Terminal.

The Astors

The Astors built their billion-dollar fortune from the fur trade and real estate. The family patriarch, John Jacob Astor, was America's first recorded millionaire. His son, William Backhouse Astor, married Caroline Schermerhorn, and she reigned over New York high society for decades. In fact, she was the one who literally defined it as “The 400.” This was said to be the number of guests Mrs. Astor's ballroom could accommodate.

Although Caroline died in 1908, New York's high society remained, and the Astor family continued among them. Her nephew, William Vincent Astor, inherited $200 million in 1912 when his father, John Jacob Astor IV, died on the Titanic. Throughout the 1930s and 1940s, Vincent became known as a great philanthropist and was the chairman of Newsweek magazine, one of the Astor family holdings.

The Rockefellers

John D. Rockefeller revolutionized the oil industry. Through the Standard Oil Company, he became the world's first billionaire. But he also believed that great wealth demanded great philanthropy. He established foundations that were devoted to specific causes that included medical research and education. Over his lifetime, he donated more than $500 million to his pet causes. During the Depression, he personally financed the construction of a fourteen-building complex in the middle of Manhattan. Through the Rockefeller Center, John became one of New York's largest real estate moguls.

Although John never drank, he wrote a letter that was published on the front page of the New York Times urging the repeal of Prohibition. He argued that the banning of alcohol simply increased disrespect for law.

The Whitneys

William Collins Whitney was a financier and prominent attorney. He married Flora Payne, the daughter of a wealthy Cleveland businessman and sister of his college friend, Colonel Oliver Payne, who introduced them. Both William and Flora could trace their family tree back to the Mayflower.

The marriage produced five children. Their middle child, William Payne Whitney — who later changed his name to Payne Whitney — increased the family fortune with his investments in banking, real estate, oil, and railroads. He was also a generous philanthropist, donating $12 million to the New York Public Library. When he died in 1927, his estate was the largest ever probated up to that time in American history. His only son, John Hay “Jock” Whitney, was a very visible member of high society in the 1930s and 1940s. Charming and affable, he was also an astute businessman. He founded the country's first venture capital firm, J.H. Whitney & Co.

The Vanderbilts

William H. Vanderbilt was considered the richest man in the world. He had inherited $100 million from his father, Cornelius Vanderbilt, and within a decade had doubled the fortune through railroad investments. When he died his son, Frederick William, assumed that title. The Vanderbilts took wealth to a level never before seen in American society. Ironically, despite the family's vast wealth, they were initially regarded as high-society outcasts, considered crass and uncouth.

After William died in 1855, his sons William K. and Cornelius II took over the family empire and brought the family respectability. The Vanderbilts' inclusion in café society was complete when Cornelius's daughter Gertrude, who founded the Whitney Museum, married Harry Payne Whitney.

The Vanderbilts enjoyed their leisure pursuits and shamelessly spent money living the good life. All of William Henry's children lived in palatial Fifth Avenue mansions and owned summer cottages out of the city. Yachting, car racing, and horses were favorite family passions. But the Vanderbilt heirs also believed in giving back to society and became influential patrons of the arts and respected philanthropists.

Prominent Families

Both the Auchinclosses and Bouviers were among the first included on the New York Social Register, along with other prominent families such as the Astors and the Roosevelts. But even among the social elite there were levels of privilege. Old money WASPs were at the top of the pecking order. The Bouviers, on the other hand, were included in spite of being Catholic, a fact that colored their peers' perception of them.

Despite their wealth, the Lee's were hopelessly nouveau and classless in the eyes of the New York society matrons in charge of the all important invitation lists to the right dinners and parties. When Janet married Black Jack, his family name gave her new credibility. Her marriage to Hughdie furthered her inclusion — as did being the president's mother-in-law.