The Colorful Life of Wall Street’s First Female Stockbroker

On a February morning in 1870, two striking sisters wearing matching outfits turned from downtown New York City’s Wall Street to Broad Street in a horse-drawn carriage to meet a crowd of thousands. Victoria Woodhull and Tennie C. Claflin were opening the world’s first female-led brokerage firm, Woodhull, Claflin, & Co., and bankers, brokers, journalists, and errand boys had turned out to see their debut.

Wearing silk bow ties over their navy jackets and solid gold pens behind their ears, and sporting daringly short skirts and hair, the sisters were dressed to impress. It was, it turned out, the opening act of a Gilded Age feminist drama that would see Woodhull run for President, embroiled in the “trial of the century,” and imprisoned in one of New York’s toughest jails.


The moment felt like a turning point for women’s rights. The Civil War had opened up employment and social mobility. Married women across the US were increasingly able to manage their own property, independent of their husbands. The 15th Amendment had just been ratified, allowing African-American men the right to vote, and Woodhull would argue before the House that this and the 14th Amendment, which addresses citizens’ rights, meant women should be able to vote. 


 A Feminist Pioneer

Born in Homer, Ohio, in 1838, to a picaresque family, Woodhull opened her brokerage for two sincerely feminist reasons: to create a place for women to invest their own money, and to demonstrate that women could thrive in perhaps the most masculine non-manual working environment of the era, Wall Street.


In 1870, there were five female lawyers among America’s 40,000-odd legal brains, and more than 500 female doctors among more than 60,000 male medics, but women had yet to make any mark on the rough-and-tumble world of finance. Or, as the Wall Street Journal reported Woodhull saying: “When I first came to Wall Street, not 100 women in the whole of the United States owned stocks or dared to show independence in property ownership. Highest-positioned men scowled at any thought of a woman’s investment. For a woman to consider a financial question was shuddered over as a profanity.”


Behind the crowds that greeted her that February day, however, lay more than curiosity about gender. The word on the Street was that none other than America’s richest man, railroad tycoon Cornelius Vanderbilt, had bankrolled the sisters. Woodhull implausibly claimed the sisters had made the then-vast sum of $700,000 trading through agents before starting their brokerage. But it seems almost certain not only that their starting capital was much smaller but that Claflin, then in her 20s, had been having an affair with the septuagenarian Vanderbilt since the sisters first worked for him, Woodhull as a clairvoyant and Claflin as a healer. 


Throughout the day, despite a sign on the door insisting “Gentlemen will state their business and then retire at once,” denizens of Wall Street came and went, one testing to see if the sisters could read their ticker tape machine (they could). Almost a century before Muriel Siebert became the first woman to purchase a seat on the New York Stock Exchange, the sisters began speculating in gold on margin and trading for female clients.


Yet Woodhull, a woman whose politics still seem radical to some in the twenty-first century, had aspirations beyond trading. For her, Woodhull, Claflin, & Co. was the means to a greater good: the furtherance of women’s rights, including not only the right to vote but free love, a concept that included the freedom to divorce, financial independence from one’s husband, and bodily autonomy. Within months of opening their brokerage, the sisters had launched a radical newspaper, Woodhull & Claflin’s Weekly.


The Road to Ruin

Just a couple of years after entering the market, however, Woodhull, Claflin, & Co. began to fail. Their gold trades proved a high-risk strategy in a volatile market, and they lost Vanderbilt’s support after Claflin admitted during a high-profile trial to having “humbugged” him. A nuisance lawsuit over a lost investment gained heavy coverage in the press, as did Woodhull’s scandalous but hall-filling speeches on free love. 


The sisters were forced to abandon their four-story Murray Hill mansion for more straitened circumstances. However, Victoria Woodhull continued to play in the gallery. In 1872, at the head of the Equal Rights Party, she ran for President, even though at 34, she was constitutionally too young to serve. The renowned abolitionist Frederick Douglass was acclaimed as her prospective vice president, although it is unclear if he ever accepted the honor.


In the early years of the decade, Woodhull had alienated the Street by adopting increasingly radical positions including publishing The Communist Manifesto, marching on the streets in support of the Paris Communards, and preaching against capitalism. Yet it was a less political edition of her Weekly in November 1872 that saw both sisters imprisoned in The Tombs, then New York’s most notorious prison.


The issue carried two problematic pieces of scandal. The first involved financier Luther Challis and a story about two underage girls. The second was that the fashionable abolitionist clergyman Henry Ward Beecher had had an affair with the wife of a protégé, Theodore Tilton. 


The first would lead to charges of libel and sending obscene material through the mail; the second exploded into a court case that many considered the scandal of the century. Woodhull would spend the election day of her presidential campaign in prison.


Within five years of opening her brokerage in a blaze of glory, a range of feuds, scandals, and allegations spanning the gamut from prostitution to spiritualist fakery, and Woodhull’s own rabble-rousing oratorical style left her on the verge of ruin. She claimed, according to the biography The Scarlet Sisters, that she’d never wanted to work the markets anyway: “We went unto Wall Street, not particularly because I wanted to be a broker… But because I wanted to plant the Flag of women’s rebellion in the very center of the continent.”


A Dramatic Third Act

In January 1877, Cornelius Vanderbilt died, leaving an estate of almost $100 million, or the approximate worth of the entire U.S. Treasury. Although he left nothing to either Woodhull or Claflin, he became their savior from beyond the grave. 


Vanderbilt bequeathed almost his entire fortune to his favorite son, William, and William’s children, sparking a lawsuit from William’s siblings claiming their father had been of unsound mind. William was said to have paid Woodhull and Claflin the fantastical sum of more than $100,000 – the equivalent of almost $3 million today – so they would be unavailable to testify.


Wealthy again, the sisters departed for England in first-class staterooms, where both would embark on impressive final acts that saw them return to the financial world. Woodhull, then approaching 40, met and married one John Martin, scion of a banking dynasty; Claflin, seven years younger, married Francis Cook, once considered one of the three richest men in Britain, and started a short-lived bank after his death.


 An early adopter of all things modern, from bicycling to automobiles to electricity, Woodhull adjusted her notorious name to Woodhall, founded a publication that campaigned, among other things, against cigarette smoking as injurious to health, and acquired an interest in eugenics. She ended her extraordinary life reigning over a quiet English country village, where the locals called her simply “Lady Bountiful.” A note found in her papers after her 1927 death read: “My life has been a long struggle to do right to the best of my ability, and God knows, if I have failed in many things, no one regrets it more than I do.”


Feuds with fellow suffragists led to her being written out of most feminist chronicles; and her colorful personal life overshadowed her short time on Wall Street. But one cannot look at women’s history in the United States without acknowledging her role as a trailblazer, even if the fires burned slowly and the trails remained difficult to navigate.