Cornelius Vanderbilt, aka “The Commodore,” was the business magnate who started it all. His investments in the Dispatch Line – the shipping route between New York and Philadelphia – drove the competition (the Union Line) out of business. In 1830, the Union Line was forced to sell to Vanderbilt.

Vanderbilt continued to buy out competitors, eventually expanding his shipping routes by the late 1850s and then getting into the railway business.

At 50, he was a millionaire. But he was also a ruthless businessman known for his “toughness and use of profanity.”

Vanderbilt took advantage of new economic opportunities on the West Coast by investing in railroads.

At first, he purchased smaller railroad companies but soon controlled all railroad travel in and out of New York City. Vanderbilt’s massive wealth helped standardize railroad procedures, timetables, and overall efficiency.

One epic moment of family drama involved custody of young future fashion icon Gloria Vanderbilt and not shipping or railways.

The granddaughter of The Commodore had a $4 million trust fund (an enormous amount of money in the 1930s) and when her father died, her mother and aunt both fought for custody of the child and her money.

Eventually, it was decided that Gloria would stay with her aunt during the school year and spend summers with her mother. You probably recognize her name because she was a renowned fashion designer in the 1970s, and many credit her with the rise of blue jeans.

William Henry Vanderbilt was the eldest son of The Commodore, and when he died his fortune was split among his children in 1885. The boys received such huge sums that they went and built massive homes.

In 1885, his son Cornelius II bought The Breakers in Newport, Rhode Island, and transformed the place into a villa. Architect Richard Morris Hunt worked to “create a 70 room Italian Renaissance-style palazzo inspired by the 16th-century palaces of Genoa and Turin.”

Hunt also handled George Washington Vanderbilt II’s home the Biltmore and remodeled the family’s “Triple Palaces” townhomes on Fifth Avenue.

Frederick William Vanderbilt was The Commodore’s grandson. And despite receiving “only” $10 million as an inheritance, he invested his money into coal, tobacco, oil, and steel and made out like a bandit.

The third son of eight children out-earned all of his older brothers. He was the director of 22 railroads all while maintaining multiple luxury homes in New York.

Frederick William Vanderbilt was worth $78 million by the time of his death in 1938. He left his fortune to schools and charity institutions.

The Commodore’s eldest son William Henry Vanderbilt also followed in his dad’s footsteps by expanding railroad operations to cities like Chicago, Cleveland, and Indianapolis.

He passed away in 1885, but at that point, the family’s fortune had increased to over $200 million – far more money than the US treasury even held!

Commodore Vanderbilt’s shipping business grew so fast that in two years, he had a contract with the US government to supply outposts during the War of 1812. Vanderbilt transported people and goods from Boston to Delaware Bay, earning $10,000 in revenue after learning about open water sailing.

But there were other shipping magnates to contend with – Robert Fulton, Robert Livingston, and Aaron Ogden had a monopoly over the route and tried to sue The Commodore.

In the end, it was ruled that interstate commerce was subject to federal regulations, and this allowed the Union Line to continue operating, raking in more than $40,000 a year in 1827. That would come out to $924,000 today.

The Vanderbilts had been Dutch immigrants who lived in obscurity in the US until Commodore Vanderbilt arrived in the early 19th century. Born in 1794, Vanderbilt borrowed $100 from his parents at the age of 16 so he could buy a flat-bottomed sailing barge called a periauger.

Vanderbilt shipped goods from Staten Island to Manhattan, working with his father. Together, they shipped cargo in the New York harbor while splitting the profit.

The young “Commodore” Vanderbilt made around $1,000 during his first year.

Cornelius Vanderbilt II’s sons, Reginald and Cornelius III (aka Neily), did not increase the family’s fortunes but instead spent their inheritance with great abandon.

Neily spent huge sums of money before falling out with his family while Reginald spent on women, gambling, and drinking.

When Reginald turned 21 years old, “he celebrated coming into his $15.5 million inheritance by losing $70,000 at the gambling table.”

Reginald married Gloria Mercedes Morgan in 1923 and she gave birth to the famous Gloria Vanderbilt in 1924.

However, Reginald’s drinking caused him to die of cirrhosis of the liver in 1925. He was broke and in debt thanks to his gambling, so he left his family with only a $5 million trust. And as we saw, that put them at each other’s throats when it came to trying to control the younger Gloria and her trust money.

Commodore Vanderbilt and Sophia Johnson had 3 sons out of a total of 13 children. One boy named George died, leaving William and Cornelius, who didn’t really get their father’s affections.

The Commodore even told William, “Any fool can make a fortune; it takes a man of brains to hold onto it.”

That’s when William Henry decided to work with one of his father’s business rivals. But, eventually, he suffered a mental breakdown and spent most of his time at the family farm in Staten Island.

However, he did recover and increased his earnings, slowly making his way into his father’s business.

Did you know Anderson Cooper is the son of Gloria Vanderbilt (and Wyatt Cooper)? Despite his pedigree, he has no trust fund in his own name.

He’s perfectly fine without having access to the family wealth though. He once told Howard Stern, “My mom’s made clear to me that there’s no trust fund… [and] I don’t believe in inheriting money.”

He even went on to say that inherited money is an “initiative sucker” and “a curse.”

The 1930s saw the shipping industry suffer amidst the new modes of transportation like cars, barges, and buses. Competitors made their way into the business, forcing the Vanderbilt family to sell shares of their railroad holdings.

Thirty years after the Commodore’s death, the Vanderbilt family was no longer among the wealthiest in the country.

The many massive homes of the Vanderbilts were filled with works of art. The family also spent money on cars, yachts, and other luxuries like lavish parties.

For example, in 1883, The Vanderbilt Ball, hosted by William Kissam Vanderbilt’s wife Alva was meant to boost the family’s status in New York society. Alva threw a costume party, inviting 1,000 people with the hopes of cementing the family name into the upper echelons of society.

The New York Times described the event as a “fairyland.” Pageantry, ornamentation, and excess dominated the event with people dressed in stunning dresses and expensive jewels.

The total cost of the ball was around $250,000 – or about $6 million in today’s money.

The Vanderbilts, along with other wealthy families, owned massive properties on Fifth Avenue. For example, the Cornelius Vanderbilt II House had a small and a large salon, a two-story ballroom, a gallery, and separate dressing rooms, bedrooms, and bathrooms all for Cornelius II and his wife.

But in 1926, the house was torn down as New York slowly changed into a city of towering buildings. The Vanderbilts did not have the money to maintain their properties so many of the houses were sold and demolished in 1926.