For his monopoly on shipping and the railroads, facilitated by political manipulation, Vanderbilt is often described as a "robber baron",[3] including in what may be one of first uses of the term, in The New York Times in 1859.

[4] Cornelius Vanderbilt's great-great-great-grandfather, Jan Aertson or Aertszoon ("Aert's son"), was a Dutch farmer from the village of De Bilt in Utrecht, Netherlands, who emigrated to New Amsterdam (later New York) as an indentured servant in 1650.

According to one version of events, he borrowed $100 (equivalent to $1,900 in 2023)[8] from his mother to purchase a periauger (a shallow draft, two-masted sailing vessel), which he christened the Swiftsure.

[14][15] In addition to running his ferry, Vanderbilt bought his brother-in-law John De Forest's schooner Charlotte and traded in food and merchandise in partnership with his father and others.

To accomplish this, he undercut prices and also brought a landmark legal case—Gibbons v. Ogden—to the United States Supreme Court to overturn the monopoly.

The Court never heard Vanderbilt's case, because on March 2, 1824, it ruled in Gibbons' favor, saying that states had no power to interfere with interstate commerce.

Using the name "The People's Line", he used the populist language associated with Democratic president Andrew Jackson to get popular support for his business.

At the end of the year, the monopoly paid him a large amount to stop competing, and he switched his operations to Long Island Sound.

Some of the first railroads in the United States were built from Boston to Long Island Sound, to connect with steamboats that ran to New York.

Many of the migrants to California, and almost all of the gold returning to the East Coast, went by steamship to Panama, where mule trains and canoes provided transportation across the isthmus.

While he was away, White conspired with Charles Morgan, Vanderbilt's erstwhile ally, to betray him, and deny him money he was owed by the Accessory Transit Company.

When Vanderbilt returned from Europe, he retaliated by developing a rival steamship line to California, cutting prices until he forced Morgan and White to pay him off.

[17] During the 1850s, Vanderbilt also bought control of a major shipyard and the Allaire Iron Works, a leading manufacturer of marine steam engines, in Manhattan.

Edmund Randolph, a close friend of Walker, coerced the Accessory Transit's San Francisco agent, Cornelius K. Garrison, into opposing Vanderbilt.

Vanderbilt sent a man to Costa Rica who led a raid that captured the steamboats on the San Juan River, cutting Walker off from his reinforcements from insurgent groups in the United States.

It helped bottle up the Virginia, after which Vanderbilt converted it into a cruiser to hunt for the Confederate commerce raider Alabama, captained by Raphael Semmes.

He suffered a grievous loss when George Washington Vanderbilt II, his youngest and favorite son, and heir apparent, a graduate of the United States Military Academy, fell ill and died without ever seeing combat.

In 1870, he consolidated two of his key lines into the New York Central and Hudson River Railroad, one of the first giant corporations in United States history.

This brought him into direct conflict with Jay Gould and financier James Fisk Jr., who had just joined Drew on the Erie board.

On August 21, 1869, in London, Ontario,[21] he married a cousin from Mobile, Alabama, with the name — unusual for a woman — of Frank Armstrong Crawford.

This left his only other living son, Cornelius Jeremiah Vanderbilt, and 9 daughters (Phebe Jane, Ethelinda, Eliza, Emily Almira, Sophia Johnson, Maria Louisa, Frances Lavinia, Mary Alicia, and Catherine Juliette), to receive comparatively little inheritance; far less than even their young nephews.

(Although his daughters and Cornelius received bequests much smaller than those of their brother William, these made them very wealthy by the standards of 1877 and were not subject to inheritance tax.)

Vanderbilt's biographer T. J. Stiles says, "He vastly improved and expanded the nation's transportation infrastructure, contributing to a transformation of the very geography of the United States.

He embraced new technologies and new forms of business organization, and used them to compete....He helped to create the corporate economy that would define the United States into the 21st century.

According to The Wealthy 100 by Michael Klepper and Robert Gunther, Vanderbilt would be worth $143 billion in 2007 United States dollars if his total wealth as a share of the nation's gross domestic product (GDP) in 1877 (the year of his death) were taken and applied in that same proportion in 2007.

In 1999, Cornelius Vanderbilt was inducted into the North America Railway Hall of Fame, recognizing his significant contributions to the railroad industry.

The 8+1⁄2-foot-tall (2.6-meter) bronze statue was sculpted by Ernst Plassmann[31] and was originally sited at the Hudson River Railroad depot at St. John's Park[32] before being moved to Grand Central Terminal in 1929.

The court battle lasted more than a year and was ultimately won outright by Billy, who increased the bequests to his siblings and paid their legal fees.

Cornelius' youngest grandson through William, George Washington Vanderbilt II, built the 250-room Biltmore Estate in the mountains of Asheville, North Carolina, as his main residence with part of his inheritance from his grandfather.

George's widow Edith Stuyvesant Vanderbilt Gerry also had to sell off additional land to pay for the estate's upkeep.