Few individuals loom larger in the story of Cornelius Vanderbilt than Daniel Drew.
If people know the name of Drew, it's probably in connection with the notorious Erie War of 1868, an episode of epic corruption and intrigue on Wall Street that was the subject of a fine book by John Steele Gordon twenty years ago. Drew battled Vanderbilt for control of the Erie Railway, short-selling the company's stock to undercut Vanderbilt's attempted corner. The Erie War created a lasting impression that the two men were enemies, that they were polar opposites.
In fact, they were only enemies for a brief, four-year period in the mid-1860s. The two men were close friends, and had been secret partners for much of their long lives.
In personality, the two men were indeed strikingly different. Drew was about the same age as Vanderbilt, but where the Commodore was tall, athletic, and fastidious about his appearance, Drew was a sly, silent, stoop-shouldered man. One observer thought he looked like "a cross between a cartman and small trader." Vanderbilt rarely poked his head into a church, but Drew was an avid Methodist who raised money for church charities and endowed a seminary (today's Drew University).
Drew began his working life as a cattle drover, and moved into New York's livestock market. He began to lend money, diversify his humble operations, and gradually became a financier. He moved into steamboats in 1831, which led him into a battle with Vanderbilt on the Hudson River. He forced Vanderbilt to buy him out, earning the Commodore's respect. But Drew remained a major force in transportation, running steamboat and railroad lines. He and Vanderbilt invested in each other's businesses, thus insuring against competition.
But it was as a player in the stock market that Drew won the most fame, and the most money. As treasurer of the Erie Railway, Drew engaged in insider trading on a massive scale, usually short-selling his own company's stock. He developed a reputation as Wall Street as the ultimate bear, the opposite of the bull Vanderbilt.
It didn't last. Drew tangled repeatedly with Jay Gould, and came off much the worse for it. He finally lost all his money shortly before Vanderbilt died (in 1877). Drew only lasted a year longer, then followed his friend to the grave.