3

Funding the Insurrection

Fog blanketed the bay as a steamship carrying Mary Ellen Pleasant coasted toward the San Francisco pier one spring afternoon. The harbor was crowded with hundreds of ships, forming a forest of masts and sailcloth, as well as dozens of abandoned vessels, rotting and sinking into the water. Late in the afternoon on April 7, 1852, the SS Oregon navigated the harbor traffic and docked after a two-month trip from the East.

When Pleasant planted her feet on California soil, rats scurried near her path on the landing, which was littered with trash and horse manure. The air was cool, and it had just begun to rain. The afternoon showers liquefied the pier’s landing and the streets, which were made of dirt and sand, turning them into mud.

Pleasant hailed a porter and a carriage to go into the city. As she recovered her land legs, she noticed the eyes of the people at the harbor peering in her direction. As she stared back, it began to settle on her that she was in a land that was simultaneously familiar and alien.

The faces of the crowd in San Francisco were overwhelmingly those of white men. They were a familiar class—Pleasant had grown up catering to their type as a young shop clerk in Nantucket—but as she moved through the harbor into the city, it became clear that the white men who filled the streets of San Francisco were different from the reserved Quakers of Nantucket. The city stretched out for three miles from a cluster of warehouses and fisheries at the pier on dirt roads that crisscrossed and ran up the town’s hills into a metropolis of fire-brick buildings and wood-frame houses that held rooming houses, saloons, banks, and shops. The gents at the pier and in the streets spoke loudly and profanely, with accents from the far corners of the world: New England, the South, Australia, and Central America. They had been lured to California by the promise of wealth in the gold rush. It was the same siren song that had called JJ away.

The men she saw in the streets were both rugged and ornate. They draped themselves in broadcloth suits with bowler hats, underneath which they wore shirts stained with dirt and tobacco spittle. The spoils of the gold rush were evident on their bodies: gold pocket watch chains, diamond-encrusted buttons on their shirts, and gold teeth dotting their smiles. Many of the men wandered the streets intoxicated, bellowing and catcalling as they bounced among gambling houses, saloons, and theaters until they finally retired to cramped, flea-infested boardinghouses, where they slept on hard cots in common rooms.

There was a handful of women in the streets near the harbor and clustered in the saloons in town. They were white, Hispanic, and Chinese, and they were dressed elegantly, with their necks and collarbones exposed in off-shoulder dresses and their hair pinned up. Pleasant would come to know these women as “entertainers,” managed by men called Macks who always lingered nigh. A woman walking down the street by herself was often such an event that men would call out, “Woman on the sidewalk!” emptying out buildings, drawing men to come and gawk at her.

Pleasant stayed in a boardinghouse operated by a friend from Massachusetts on Washington Street in an area called Sydney Town. The area was near the pier and was made up of boardinghouses constructed from converted warehouses and abandoned ships dragged from the pier. The alleys were patrolled by thieves and muggers. Sydney Town was the stomping ground for the Sydney Ducks, a gang made up of immigrants from the British penal colony in Australia. The area was also home to black and Irish workers, who, due to the surging housing prices during the gold rush, couldn’t afford to live anywhere else. Pleasant found lodging in the company of friends, which she hoped would help her avoid trouble in her new home.

In her first days after she settled in the city, she got a fix on her husband, JJ: he had gotten a job as a cook on a steamship that operated between California and Panama. Pleasant decided to try to find her own fortune in California. As a black woman in the gold rush, and one of means, she intuited that her best opportunity to make money would be as an investor.

So she became a moneylender. San Franciscans seemed always to need capital. Some were just getting started in the city after having spent their life savings to get to California; others were spendthrifts, blowing through their money almost as soon as they earned it, bingeing on prostitutes, gambling, and liquor. The cash-strapped nature of her fellow Californians provided an opportunity to Pleasant, who came to the city with plenty of money. She gave some of it to connected men and let them lend it out at 10 percent interest per month. Ten percent a month was a rate that, when collected upon, would more than double her capital every year.

Pleasant navigated the town’s streets on foot or by carriage, carrying thousands of dollars of currency with her at a time, moving between the Victorian homes of the north to the rough streets in the city’s south, making deposits and withdrawals. “I divided this money between Fred Longford, William West of West & Harper,” she began. After dropping off money and picking up her interest payments, she then continued to “Thomas Randolph who lived on Green Street, between Stockton and Dupont.” Randolph operated in North Beach, a wealthy enclave on the city’s northern shore known for its hills and a Russian cemetery, where the area’s children played among the grave markers. “I had known these gentlemen from home. We put our money out at ten percent interest per month,” she reminisced. “Those were the good times of ’49.”

In addition to lending money, Pleasant peddled silver. She had connections with silver buyers and sold large quantities at good margins. “I always had friends in places where a good deal of silver was required,” she recalled. One of her greatest strengths was making friends, from her days as a shop clerk in Nantucket when she had “let books alone” and “decided to study men and women.” She became a master of human connection. Her ability to bond with others took her from shop clerk to wife of a wealthy man. As a widow she found another man, Captain Edward Gardner, to liquidate her late husband’s estate. Pleasant had made friends everywhere she went, from Nantucket to Boston, and now she did the same in the international town of San Francisco. “When I have attached myself to one as a friend, I have remained to the end,” she later said. Her networking ability allowed her to set up businesses lending out money and selling silver, which above all else required knowing the right people who knew the right people.

One of the ways she got her hands on silver was to sell and ship gold to Panama, receiving silver in return. “I did an exchange business with Panama sending down $1000 of gold [$26,000] at different times and having it changed into silver,” she recalled. “Gold was then at a high premium,” she continued, and in San Francisco she could get her hands on large quantities of it.

Pleasant also got her hands on silver through California’s banks. She would routinely make her way to San Francisco’s financial district, a series of banks and shops near the pier, where she would enter the Wells Fargo & Co. bank. The bank was a rectangular fire-brick building with wood-shuttered windows. Men in top hats and jackets and the company’s stagecoach were frequently out front. Inside there was a large storeroom in the front, paneled with dark wood, and a counter in the back with a large scale on it. “My custom was to deposit gold and draw out silver, by which means I was able to turn my money over rapidly,” Pleasant remembered. Once Pleasant had acquired as much silver as she could get her hands on in San Francisco she found buyers to purchase the silver for an incrementally higher price than she paid for it. The difference in price accumulated over multiple transactions into tens of thousands of dollars of profit. In her early days in San Francisco Pleasant was making between $15,000 and $25,000 a year ($392,000 and $650,000, respectively). By 1858, she was worth more than $150,000 ($4.2 million).

Her success as an investor was a mystery. Some speculated that she had such good fortune through voodoo. Others speculated that she learned to invest by trading sex for financial advice with San Francisco’s rich bachelors. Another popular rumor said she eavesdropped on business conversations during the dinners she catered. “I have never been given to explaining away lies, and you can’t explain away the truth,” she would say. The truth is that the gold rush was an opportunity that the circumstances of Pleasant’s life up until that point had prepared her for. Having been reared in a boomtown that featured women and African Americans taking part in its prosperity, Pleasant had used her days in the whaling years of Nantucket to prepare her for gold rush San Francisco. In many ways, her success was not unusual; many of the most successful participants in the gold rush came from whaling towns such as Nantucket and New Bedford. Nonetheless, for decades going forward, the brilliant black gold rush investor would confound racial stereotypes and popular explanation.

MARY ELLEN PLEASANT’S MOVES WHEN SHE ARRIVED IN SAN FRANCISCO were shrewd but unspectacular. Those whom she made her money off likely did not even know she existed. As a woman and an African American, she had been discriminated against and overlooked most of her life. By the time she arrived in San Francisco, she had learned to work in the background. Moving out west allowed her to keep an eye on her new husband, grow her bequest, and make plans without drawing any more attention to herself than necessary. But what was she planning on for the long run?

Life in California was profitable, but she missed her home and the struggle back east. There had to be a purpose to it all, besides keeping tabs on JJ. Pleasant was disconnected from her old life, but she willed what pieces of home she could to her surroundings. She socialized with other Nantucketers and Bostonians. She made her favorite dishes, serving pineapple upside-down cake and honey-baked ham for friends at the private dinners and banquets she catered for extra income. She corresponded long distance with friends. She also made special efforts to procure abolitionist periodicals such as William Lloyd Garrison’s The Liberator and Frederick Douglass’ Paper from the East.

In the spring of 1852, as her wealth increased, Frederick Douglass’ Paper printed a series of essays on black wealth. The series, by James McCune Smith, a public intellectual and the first African American to earn a medical degree, pondered whether free blacks should use their liberty to pursue wealth, abolition, and civil rights. “Hundred thousand dollar black men would be no better than hundred thousand dollar white men,” he wrote. “Gold freezes up the humanities and all their surroundings. The wealthy are never a progressive class; they are by necessity conservatives.”

In one installment Smith compared Samuel Ringgold Ward, an abolitionist, and Jeremiah Hamilton, the richest black man in New York, asking who was the better man. Ward was an abolitionist whom Pleasant knew through his nephew Rev. Thomas Marcus Decatur Ward; he lived in San Francisco and presided over the African Methodist Episcopal Church where Pleasant worshipped. Hamilton was a free black man, and like Pleasant, he was an investor. He was worth at least half a million dollars and lived in a brownstone in lower Manhattan. Hamilton shunned abolitionist causes and, like Pleasant’s first husband, defined his race as Cuban.

Compare Sam Ward with the only black millionaire in New York, I mean Jerry Hamilton; and it is plain that manhood is a “nobler ideal” than money. The former has illustrated his people and his country, the other has fled from his identity (to use the elegant phraseology of Ethiop), like a dog with a tin kettle tied to his tail!

Wealth and activism were binary characteristics, Smith argued in the United States’ most distributed black newspaper of the antebellum period. One could either seek liberation or seek wealth, not both. As she often did when presented with two conflicting ideas, Pleasant harmonized them as only she could. She set her mind to pursue wealth but to the end of using the money she made to seek liberation for slaves, as she had promised her husband to do. Around the time that Smith printed his treatise on Hamilton and Ward, Pleasant began to become interested in a name she saw printed in the papers: John Brown.

John Brown was the most belligerent opponent of slavery since Nat Turner earlier in the century. He was a white shepherd and Calvinist preacher who believed that God wanted him to bring an end to slavery. He first made headlines when he founded an armed security force in Springfield, Massachusetts, called the League of Gileadites, the local branch of a national organization, to defend runaway slaves. William Wells Brown, an acquaintance of Pleasant, wrote on encountering the League of Gileadites on a visit to Springfield, “[W]e found there some ten or fifteen blacks, all armed to the teeth and swearing vengeance upon the heads of any who should attempt to take them.”

In 1854, President Franklin Pierce, an anti-abolitionist Democrat, signed the Kansas-Nebraska Act into law, sending slavery’s opponents into a fury. The law, authored by Illinois senator Stephen A. Douglas, created the territories of Kansas and Nebraska but also allowed for the expansion of slavery into the North, where it had been banned since 1819. Slavery would be permitted or banned in Kansas, a northern territory, based on a popular vote among white males in the territory. The law would potentially reintroduce slavery into the North, endangering freedmen and -women and reinforcing slavery’s grip on America. Frederick Douglass and William Lloyd Garrison published angry treatises against it in their papers. On the steps of the courthouse in Peoria, Illinois, a largely unknown politician named Abraham Lincoln gave a three-hour speech decrying the law. “I hate it because of the monstrous injustice of slavery itself. I hate it because it deprives our republican example of its just influence in the world,” he told hundreds of onlookers. Afterward, his Peoria speech became a thing of legend that catapulted him into national prominence.

Pleasant kept abreast of the developments. Proslavery and antislavery supporters rushed into the territory to try to influence the outcome, and the tug-of-war eventually became violent. Brown’s name reappeared in the papers when he and his sons went to Kansas to lead the fight during “Bleeding Kansas,” a battle between slave owners and abolitionists. After rumors circulated that he had been killed during Bleeding Kansas, he surfaced with an essay entitled “Parallels” that was published in several abolitionist papers:

On Sunday, the 19th of December, a negro called Jim came over to the Osage settlement from Missouri and stated that he together with his wife, two children, and another negro man were to be sold within a day or two and begged for help to get away. On Monday (the following) night, two small companies were made up to go to Missouri and forcibly liberate the five slaves together with other slaves. One of these companies I assumed to direct. We proceeded to the place, surrounded the buildings, liberated the slaves, and also took certain property supposed to belong to the estate.

We, however, learned before leaving that a portion of the articles we had taken belonged to a man living on the plantation as a tenant, and who was supposed to have no interest in the estate. We promptly returned to him all we had taken. We then went to another plantation where we freed five more slaves, took some property and two white men. We moved very slowly away into the Territory for some distance and then sent the white men back, telling them to follow as soon as they chose to do so. The other company freed one female slave, took some property, and as I am informed, killed one white man (the master), who fought against the liberation.

Now for a comparison. Eleven persons were forcibly restored to their natural and inalienable rights, with but one man killed, and all “Hell is stirred from beneath.” It is currently reported that the Governor of Missouri has made a requisition upon the Governor of Kansas for the delivery of such as were concerned in the last-named “dreadful outrage.” The marshal of Kansas is said to be collecting a posse of Missouri (not Kansas) men at West Point in Missouri, a little town about ten miles distant, to “enforce the laws.” All proslavery, conservative free-state, and dough-faced men, and administration tools, are filled with holy horror.

Brown took the slave he freed to Ontario and then disappeared into hiding. Shortly after Brown published “Parallels,” Pleasant considered leaving San Francisco for the free black settlements in Ontario. There she hoped she could learn how to find him. “I had no well-defined idea of just how I was to help John and concluded to see what could be done after I reached [Canada],” she recalled.

AS PLEASANT WAS MAKING PLANS TO HELP BROWN STRIKE A BLOW against slavery, the rights of minorities in California were eroding. The pull of California’s prosperity made it diverse, drawing people from all races, regions, and backgrounds to San Francisco. Many white men, however, saw the Hispanics, blacks, and Chinese immigrants who were present in large numbers in the city as stealers of white men’s jobs and opportunities. Minorities were blamed for the city’s crime and forced to live in ghettos, while taxes and legal restrictions on immigrants were made into law. In a landmark case in 1854, the California Supreme Court passed a law that banned blacks, Indians, and Chinese from testifying against white men in court. The ruling coincided with a high-profile lawsuit, Folsom v. Leidesdorff, in which the family of the deceased black millionaire industrialist William Leidesdorff was suing the prominent white Californian Joseph Folsom. Leidesdorff’s family claimed that Folsom had conned them into signing over the Leidesdorff estate to him. Leidesdorff’s black family members’ testimony in the suit was deemed inadmissible, making mounting a case difficult. Pleasant donated to the effort to overturn the laws that disenfranchised minorities but kept her focus on a bigger fight: the struggle to end slavery.

LATE IN MARCH 1858, THERE WAS A KNOCK AT PLEASANT’S DOOR AT her and her husband’s dwelling in San Francisco. On the other side was a portly young man named William Alvord. He gave her two steamship tickets for New York. She had learned that John Brown was going to address an African American expatriate community in Chatham, Ontario, in Canada and had decided to go there and try to meet him. She sent out a few letters and withdrew a large sum of money before she left. “I took with me in addition to the money needed for expenses, a thirty-thousand-dollar US Treasury draft, which I decided to give to John Brown,” she recalled.

On April 5, 1858, Pleasant and JJ went to the San Francisco pier and boarded a steamship for New York. The ship dropped anchor in the East River and docked at a crowded port on the east side of Manhattan. Pleasant’s old friend Captain Edward Gardner received the couple. Gardner had dark hair and a clean-shaven face and was dressed in a dark suit. He looked much older than when Pleasant had last seen him; the skin of his face drooped around his eyes, chin, and cheeks.

Gardner took Pleasant and JJ into town and helped get them set up at a colored boardinghouse. Pleasant did not want to spend too much time in New York before beginning the final leg of their trip. Her plan was to take the money she had brought for John Brown and convert it into a draft on a Canadian bank. After she did so, she and JJ caught a steamboat at New York Harbor that night for Chatham, a town just across the Detroit River on the Canadian side of the border, where she hoped to find John Brown.

CHATHAM WAS A TOWN OF FARMS AND SMALL SHOPS BUILT ALONG the Thames River, and the train tracks ran along it. When Pleasant arrived, the city already had a large population of blacks composed of runaway slaves and expatriate freedmen from America. In May 1858, John Brown came to town to meet with the black population for what he called a Provisional Constitutional Convention. More than forty Chatham residents met in a schoolhouse in secret, away from the gaze of the white residents. They told the townspeople they were meeting to discuss the formation of a new Masonic lodge. Their plan backfired as curious townspeople gathered around the schoolhouse, peering in the windows.

They convened just after 10 a.m. Dr. Martin Delany, a black man with thinning hair, dark skin, and downturned eyes, stood to address the attendees. They were there to discuss a plan to form a new free territory in West Virginia. After Delany, Brown stood to explain his scheme in detail. As he began to speak, he was interrupted by Delany, who insisted that everyone swear an oath of secrecy before Brown revealed anything. “I solemnly affirm that I will not in any way divulge any of the secrets of this convention, except to persons entitled to know the same, on the pain of forfeiting the respect and protection of this organization,” he stated. The attendees repeated the oath after him.

Brown told the gathering that he planned to form a militia in West Virginia, liberate several slave plantations, and establish a free territory and military stronghold in the Appalachian Mountains. It would be a place slaves could escape to, a permanently free, multiracial community. He assured his listeners that his plan would be successful because he had been studying insurrectionary warfare, particularly the history of the Haitian Revolution and the military strategy of Toussaint L’Ouverture. He planned to establish the territory by staging a slave insurrection in West Virginia after he sacked the US armory in Harpers Ferry for weapons. He also had a provisional constitution he had written for the new region read aloud. It was voted on and ratified. The men and women present hugged and thumped one another on the back in congratulations.

The next day the convention convened again at 6 p.m. for provisional elections for the new territory. John Brown was nominated and confirmed as commander in chief of the new region, and a freeman named J. H. Kagi was named secretary of war. The convention’s attendees could not agree on who would be president and argued until nine the next morning. After a recess they reconvened, and Brown suggested that they postpone selecting a president. The motion carried. They then elected members of Congress from the attendees and adjourned at 2 p.m.

Following the meeting, Mary Ellen Pleasant arranged to have a one-on-one with John Brown. At the meeting she gave him a bank draft for $45,000 ($1.3 million). “I turned the whole amount over to John Brown and his son one night in my room,” she later said. They then went over the details of Brown’s plan. “John Brown and I talked it over but we did not confide the details to our friends.” Pleasant knew many of slaves on the West Virginia plantations. She told Brown she would help spread the word of the planned slave revolt. “I told him that by the time he had organized for his fight I would have the blacks in a state of insurrection and near at hand to come in with reinforcements,” she recalled. “With this agreement, we parted.”

After the convention, Mary Ellen Pleasant and JJ began to put down roots in Canada. After meeting Brown, she traveled to Montreal for an abolitionist convention, where she met up with some of her and her husband’s old friends. “Wendell Phillips and Geo Green called on me in Montreal, but I did not tell them of my plans with Brown,” she recalled. “I know there was to be bloodshed and concluded not to talk it over with them.” She wanted to keep Brown’s insurrection and her role in it a secret.

Pleasant left Canada and traveled to West Virginia, where she went from plantation to plantation, talking with the slaves about Brown’s plan for a revolt. “They were very much taken with the idea of participating in the fight for their freedom,” she recalled.

The fall after the convention, she and JJ returned to Canada and purchased four connected lots of land overlooking the Thames River to build a homestead. She also purchased a silver revolver with a long barrel and joined the Chatham Vigilance Committee and Militia with the aim of protecting the black community in Chatham. There were fourteen members of the militia. Joining them were the organizers of the Brown meeting, Martin Delany, and the abolitionist publishers William Howard Day and Mary Ann Shadd Cary, all of whom had relocated to Chatham around the same time as the Pleasants.

In the fall of 1858, a slave catcher kidnapped a teenage black boy in London, Ontario, a few miles up the tracks from Chatham. The fourteen members of the vigilance committee were alerted and met at the train tracks carrying their weapons. When the train arrived, they boarded it and searched for the boy. They found him in the back of the train, seated next to his captor. At gunpoint, they removed him from the train and retreated back into Chatham.

AFTER THE TRAIN RESCUE, PLEASANT WAS INVIGORATED AND BEGAN writing to John Brown in anticipation of his revolt. “The ax is laid at the root of the tree. When the first blow is struck there will be more money and help,” she wrote.

John Brown began his raid the month after the train robbery, to the dismay of his collaborators, whom he had promised he would wait until he was better prepared. He was undersupplied and undermanned, with only eighteen men in his militia and a small supply of artillery. In the first hours, they were successful: he and his men captured hostages, including George Washington’s great-grandnephew Lewis Washington, and took control of the areas surrounding the armory by early the next morning. Brown had hoped that word of his effort would spread to local slaves, who would come to his aid to reinforce their ranks. They, however, were unaware of what was happening. By the afternoon, Brown and his men were surrounded by a local militia and holed up in a barn. A day later, they were captured.

Pleasant was devastated when she learned that his plan had been foiled. “I was astounded when I heard that he had started in and was beaten and captured and that the affair upon which I had staked my money and built so much hope was a fiasco,” she recalled. Her disbelief turned to worry when she realized that she was in danger if it were found out that she had helped Brown. “We began to look about for our own safety, for we read in the papers that all of Brown’s fellow conspirators were being sought for by the authorities. When they captured him they found among his papers a letter from me.”

A year after his failed raid, Brown was tried and executed by hanging. “I often wished that I went up on that scaffold with him,” she lamented. For the time being, she went into hiding and tried to figure out what she would do next.