During the late 19th and early 20th centuries, Fifth Avenue in New York City became synonymous with wealth and luxury. Among the affluent families who owned grand mansions along this iconic street were the Vanderbilts, including Cornelius II’s opulent 130-room residence. However, in 1926, the Vanderbilts’ legacy on Fifth Avenue came to an end. As real estate developers clamored to build skyscrapers, the Vanderbilts were forced to sell their properties, including the Cornelius Vanderbilt II House and William Kissam Vanderbilt’s Fifth Avenue home, both of which were subsequently demolished.

By the time Cornelius “Commodore” Vanderbilt’s grandchildren inherited the family’s wealth, the Vanderbilts’ economic supremacy was waning. By the 1930s, advancements in transportation, such as cars, barges, and buses, were diminishing the shipping industry’s significance. Additionally, the family divested shares of its railroad holdings, allowing competitors to gain majority control. For instance, the Chesapeake and Ohio Railroad acquired a substantial amount of New York Central stock and assumed leadership, leading the company into bankruptcy in the 1950s and 1960s.

Within three decades of Commodore’s passing, no Vanderbilt family member ranked among the wealthiest individuals in the United States. By 1973, not a single attendee of the Vanderbilt family reunion, which comprised 120 individuals, possessed millionaire status.

Cornelius “Commodore” Vanderbilt, though not renowned for philanthropy, notably donated $1,000,000 to what later became Vanderbilt University. However, it was during the Gilded Age that his grandchildren established the family as significant philanthropists.

Louise Holmes, wife of Frederick Vanderbilt, was generous in the Hyde Park area, aiding education and establishing a Red Cross chapter. The Vanderbilts organized community events and Frederick left a portion of his wealth to employees upon his death.

William Kissam Vanderbilt supported Columbia University, the YMCA, and invested in New York tenement housing. George Washington Vanderbilt II funded libraries, arts activities, and education. Gertrude Vanderbilt Whitney, an artist, supported female artists using family wealth.

This philanthropic era marked the beginning of the Vanderbilt family’s financial decline.

CNN news anchor Anderson Cooper, son of Gloria Vanderbilt and Wyatt Cooper, has long been aware that he won’t inherit any of the family fortune, and he’s comfortable with that. He openly shared with Howard Stern that his mother made it clear there’s no trust fund for him, and he personally doesn’t believe in inheriting money. In fact, he views inherited wealth as a deterrent to initiative, even calling it a “curse.”

Despite his mother’s wealth, Cooper had a job growing up and relates more to his father, who came from humble beginnings in Mississippi. Cooper, who earns millions annually from his CNN career, values the idea of making his own way in the world rather than relying on inherited wealth.

Commodore Vanderbilt married his first cousin Sophia Johnson in 1813, and the couple had 13 children together, 11 of whom survived into adulthood. Among their offspring were three sons, but tragically, George passed away in 1864. The two surviving sons, William and Cornelius, did not earn their father’s admiration. Commodore often disparaged William as a “blatherskite,” or a fool, and had Cornelius confined to an asylum on two occasions. Despite this, Commodore chose to leave the bulk of his wealth to William, advising him that “any fool can make a fortune; it takes a man of brains to hold onto it.”

William Henry Vanderbilt experienced a mental breakdown in his youth after collaborating with one of his father’s business rivals. Subsequently, he spent much of his time at the family farm in Staten Island, where he successfully increased its profitability. Over time, William became more involved in his father’s railroad enterprises, eventually assuming control after Commodore’s passing.

Cornelius Vanderbilt II’s youngest son, Reginald, inherited a small sum, while the bulk of the family fortune went to his older brother, Alfred. The eldest son, Cornelius III, struggled financially, feeling left out of the family’s wealth growth.

Reginald, known as a playboy, indulged in gambling and drinking. Upon inheriting $15.5 million at 21, he lost $70,000 in one night. His excessive lifestyle led to his death from alcohol-related illness. He married Gloria Morgan in 1922, and their daughter, Gloria, was born in 1924. Reginald died a year later, leaving his family in debt and relying on his daughter’s trust fund interest.

The Vanderbilt family, originally from the Netherlands, immigrated to the United States in the late 17th century. Initially farmers, they lived modestly until Commodore Vanderbilt emerged in the early 19th century.

Born in 1794, Commodore Vanderbilt displayed entrepreneurial spirit from a young age. At 16, he borrowed $100—equivalent to about $2,000 today—from his parents to purchase a periauger, a flat-bottomed sailing barge. Breaking away from his father’s ferry business, Vanderbilt began transporting cargo independently in the New York harbor. With astute advertising and competitive pricing, he quickly outperformed his rivals, earning approximately $1,000—around $21,000 today—in his first year. Soon, he expanded his operations, building a small fleet of ships.

Commodore Vanderbilt wasted no time in leveraging his $100 investment to rapidly expand his shipping enterprise. Within just two years, he secured a contract with the US government to supply outposts during the War of 1812. Vanderbilt’s fleet grew, and he immersed himself in ship design and open-water sailing. By the war’s end, his revenue from transporting people and goods from Boston to Delaware Bay had soared to $10,000.

In 1817, Vanderbilt partnered with Thomas Gibbons to operate steamships ferrying passengers between New York and New Jersey. Despite challenges posed by the state shipping monopoly held by Robert Fulton, Robert Livingston, and Aaron Ogden, their Union Line flourished. The landmark Supreme Court case Gibbons v. Ogden in 1824 affirmed federal authority over interstate commerce, allowing the Union Line to operate freely. By 1827, the Union Line’s annual earnings exceeded $40,000, equivalent to approximately $924,000 today.

William Henry Vanderbilt, born in 1821, continued his father’s business legacy by expanding railroad operations from New York to cities like Chicago, Cleveland, and Indianapolis. Between 1877, when his father passed away, and William Henry’s own death in 1885, the Vanderbilt fortune surged from $100 million—more than that of the U.S. Treasury—to over $200 million, largely due to William Henry’s business acumen.

Upon William Henry’s death, his wealth was divided among his eight children—four daughters and four sons. The family’s share in the company was bequeathed to the two eldest sons, Cornelius Vanderbilt II and William Kissam Vanderbilt, who assumed control of the enterprise after their father’s retirement in 1883.

After William Henry Vanderbilt’s death in 1885, his fortune was divided among his children. Cornelius II received $80 million, William Kissam got $60 million, and the two younger sons got $10 million each. They made significant investments with their wealth.

Cornelius II bought The Breakers in Newport, Rhode Island, in 1885, turning it into a lavish villa with architect Richard Morris Hunt’s assistance. Hunt also designed George Washington Vanderbilt II’s Biltmore estate in North Carolina and William Kissam’s “Petit Chateau” in New York City. The Vanderbilts owned multiple properties on Fifth Avenue, including the “Triple Palaces” and Cornelius II’s townhouse, the largest residence ever built on Manhattan Island.

Despite receiving less inheritance, Frederick William invested wisely in coal, tobacco, oil, and steel, amassing a fortune of $78 million by his death in 1938. He owned properties like Rough Point in Newport and lived in Hyde Park, New York.

Gloria Vanderbilt’s upbringing was marked by absence and instability. Raised mostly by a nurse due to her mother’s neglect, she found stability and care with her aunt, Gertrude Vanderbilt Whitney. A legal battle ensued over custody, with Gertrude refusing to yield, citing her sister-in-law’s unfitness. Eventually, a compromise was reached: Gloria spent school years with her aunt and summers with her mother.

As a teenager, Gloria embraced a socialite lifestyle and briefly dabbled in Hollywood before returning to New York for art and acting pursuits. Later, she found success in fashion, initially with jeans in the 1970s. Gloria built her own financial success, leveraging her family’s legacy.

Commodore Vanderbilt, after failing to buy out Thomas Gibbons’s son, launched his own steamship venture, the Dispatch Line. By 1830, he acquired the Union Line and expanded his influence along the East Coast, eventually reaching the Atlantic.

Transitioning to railroads, he consolidated small companies, creating a monopoly in New York City and standardizing operations. Despite his immense wealth, he was known for his toughness and lack of philanthropy. When he died in 1877, his descendants inherited his $105 million estate.

Watch to see how this family went from American royalty to flat out broke.