What Elizabeth Key Grinstead, Mary Richards (Mary Bowser), and Mary Touvestre can Teach Us About Being Wily!
In this era of backsliding rights, voter suppression, book bans, and open descent into authoritarian rule in the U.S. and around the world, resistance requires being slick and sly. This edition of #SistoryLessons honors three women who outfoxed slavery.
Using their smart brains, crafty instincts, and ability to disappear into other identities (or sometimes disappear altogether), Elizabeth Key Grinstead, Mary Richards (aka Mary Bowser, among other names), and Mary Touvestre demonstrate a lineage of Black women who subverted and survived. I find their stories very inspiring, especially in times like these!
These three women, possessing no rights under the law, nevertheless used convention, subterfuge, and collective courage to destabilize a regime built on slavery. When we think of them, what do we feel encouraged to try?
Take note: There are no photographs nor verified quotes from these three Brave Foremothers in the public record, so we can only imagine what they might have said, based on the valiant lives they led and the convictions they held.
And with no photos or portraits to draw from, we will just adorn them with flowers this edition. (The photo generally attributed to being of Mary Bowser is of a different Mary Bowser!)
Elizabeth Key Grinstead: Forging a Legal Precedent - The First Woman to Successfully Sue for Her Freedom (1630 – January 20, 1665)
Elizabeth Key Grinstead’s astonishing 17th-century freedom lawsuit exposes the twisted logic of early colonial enslavement and the irrational “mathematics” of racial purity.
Born the illegitimate daughter of Thomas Key, a white English landowner, and an enslaved Black woman (whose name the historical record does not seem to have preserved), Elizabeth was six when her father returned to England. When he left, he entrusted her to a wealthy Virginia tobacco planter under a promise that she be treated as part of the household and freed at age fifteen.
But after Key’s death, that agreement was ignored. The planter sold Elizabeth to another owner who moved her to a more remote part of Virginia, and her servitude deepened.
Among the new farmer’s indentured servants was William Grinstead, an Englishman who had sold himself into labor hoping to make his fortune in the New World. Elizabeth and William fell in love and had a son together. By then, William’s term had ended, and, no longer indentured, he had begun studying law. When Elizabeth’s second enslaver died in 1655, his heirs—seeking to retain ownership—classified her as a “Negro” and claimed her and her child as inherited property.
Refusing to accept that fate, Elizabeth sued for her freedom, with William serving as her legal counsel. They argued that because her father had been a free Englishman and she a Christian, Elizabeth herself should also be free. After multiple appeals and reversals, the Virginia General Assembly ruled in her favor on July 21, 1656—a stunning victory in an era of rigid racial hierarchy. Elizabeth and William then formally married and had another child, settling in Virginia’s Northumberland County, where they raised two sons before William’s early death.
She lived out her life as a free woman of mixed heritage in a society that was rapidly codifying racial bondage—a precarious position that demanded resilience and discretion. The Grinstead family’s descendants—some of whom moved west and blended into white or mixed communities—carried on her legacy of perseverance.
As you can imagine, her groundbreaking case terrified Virginia’s slaveholding elite. In 1662, the colony enacted a new law declaring that a child’s legal status—and condition of freedom or enslavement—would follow that of the mother, not the father, closing the brief legal opening her case had created and setting the stage for the “one drop” rule that would relegate so many children of enslaved Black women and their white enslavers (rapists) to a life of enslavement as well. This statute ensured that for the next two centuries, white men could exploit and enslave the children born from their assaults on Black women without legal accountability—and in this way, many enslaved Black women became, as you are likely aware, little more than breeders.
As horrific as this reality is, I want to give Elizabeth some flowers for the courageous way she used the courts. Elizabeth Key Grinstead’s victory was both monumental and bittersweet: a rare moment when a Black woman prevailed within the colonial legal system, even as her triumph provoked laws designed to prevent such justice from ever occurring again. Her legal victory stands as one of the earliest documented successful freedom suits in colonial America and foreshadowed future generations of Americans who would turn to legal strategies in the struggle for liberty and justice.
I can imagine Elizabeth saying this if she were alive today ... “I learned early that the law could be a wship—or a key—and I chose to make it unlock the door for my child and me.”
Reflection: What argument for your (or others') humanity do you refuse to stop making?
Mary Richards (Bowser): Many Names, One Great Cause - The Spy of Many Names (ca. 1846 – unknown)
When I was writing my book, I watched a fascinating documentary about Mary Richards. Because she was a spy and had over half a dozen pseudonyms, hers was one of the most difficult profiles to assemble. Since then I've seen a lot more interest and short videos about her life. Maybe my book and revelation inspired others to dig into her past! (I'd like to think so, at least!)
Mary Richards, later known as Mary Bowser, used intelligence, a photographic memory, and the very invisibility imposed by enslavement to become a Union spy associated with Elizabeth Van Lew’s Richmond network. Virginia abolitionist Van Lew could not legally emancipate the people she inherited, but she quietly singled out young Mary—baptized in May 1846—for opportunity, sponsoring her education in the North and arranging for her to sail to Liberia in 1855 as part of a missionary project to the West African nation founded by formerly enslaved people from the United States.
Mary hated life there and petitioned to come home. When she returned via Baltimore in 1860 and made her way back to Richmond, state law barring educated or emancipated Black people from resettling in Virginia meant she was arrested as an illegal free Black person. By paying the ten-dollar fee and claiming Mary as “hers,” Van Lew turned a racist statute into cover, perpetrating the front that Mary remained her property while all the while working with her as an anti-Confederacy co-conspirator.
This was not her last spy move, not by a long shot. When Richmond became the Confederate capital, Van Lew and Mary began moving through the city as if they were simply a pious lady with her harmless servants. Sometimes feigning eccentricity or feeble-mindedness, they visited makeshift prisons—including Richmond’s Libby Prison—to bring food, clothing, and medicine to Union captives, slip in coded messages, and help orchestrate daring escapes from the disease-ridden former tobacco warehouse. By late in the war, Union commanders formally recognized the value of this underground network; by 1864, Van Lew and key members of her household, including Mary, were on the U.S. government payroll as spies.
During these years Mary married Wilson Bowser, another enslaved man connected to the Van Lew household, and the name “Mary Bowser” entered the story. Some historians say her most famous exploit—reportedly infiltrating the household of Confederate president Jefferson Davis, often called the Confederate White House, under the guise of a seemingly uneducated domestic worker—may include some embellishment, but what is clear is that she used her education and keen intelligence, along with white assumptions about Black “ignorance,” to move through elite Confederate spaces without being seen as a threat, listening in on conversations, reading documents left on desks, and passing military and political intelligence out through Van Lew’s network. Van Lew later praised the Black operatives in her ring as the sources of her “most reliable” information, singling out Mary’s discretion and courage as indispensable to the Richmond underground.
After the war, Mary stepped briefly into public view under yet another alias. In September 1865, New York papers announced a lecture by “Richmonia Richards,” a “colored woman” recently from Richmond who had served in the Secret Service and was now organizing schools for Freedpeople. In her talks she described her espionage work, the brutal conditions in Confederate prisons, and her new vocation as a teacher, insisting that emancipation without political rights and real justice was not enough.
Mary went on to teach in freedmen’s schools in Virginia, Georgia, and Florida, signing letters as Mary J. Richards or Mary J. R. Garvin and challenging even the Freedmen’s Bureau when she saw racial inequities. She declined Van Lew’s postwar invitation to return and live quietly in Richmond, preferring an independent life on her own terms—and then, like many great spies, she vanished from the archival record, leaving behind only aliases, fragments, and a legacy of audacious resistance.
What an ingenious and daring operative Mary Bowser (etc.) was! I love how she went from enslaved to emigre to emissary for stratagem! And I especially love how she said “no, thank you” to Van Lew’s offer to return to Richmond and instead elected to live out her life on her own accord.
I can imagine Mary saying this if she were alive today: "They thought I was 'just' a servant, too dim to imagine I would be the witness who remembered every word and helped end their war.”
Reflection: When does invisibility protect your mission or cause?
Mary Touvestre: Super-Spy -The Spy Who We Love (ca. 1812 – 1883)
Mary Touvestre (also known as Mary Louvestre or Louveste) was a formerly enslaved Black woman whose quiet act of espionage helped alter the course of the Civil War at sea. Working in the home of a Confederate engineer in Norfolk, Virginia, she risked her life to spirit stolen ironclad ship plans to Washington, D.C., giving the Union Navy critical intelligence at a pivotal moment.
Born enslaved in Virginia around 1812, likely in or near Norfolk, she was living by the 1860s as a free Black woman in a slaveholding city under Confederate control, supporting herself as a housekeeper and seamstress in the household of an engineer tied to the Gosport (Norfolk) Navy Yard—a Confederate engineer involved in converting the scuttled, burned USS Merrimack into the ironclad CSS Virginia.
From inside this home, she overheard conversations and saw drawings and technical documents that revealed the ship’s destructive potential against the Union fleet in Hampton Roads. When she realized the significance of the secret plans being discussed and drawn in the home, she took or copied a set of them and set out for Washington, D.C., traveling roughly 200 miles through contested territory in the dead of winter as a Black woman carrying incriminating military documents and facing constant danger of exposure, arrest, or execution as a spy.
In the capital she obtained a private audience at the Navy Department, was brought before Secretary of the Navy Gideon Welles, and delivered both the plans and her account of the ironclad’s near completion and intended use against the blockading fleet. Welles’s records and later accounts suggest that Mary’s intelligence confirmed and sharpened existing reports about the Virginia, underscoring the urgency of finishing the Union ironclad USS Monitor and helping spur the Navy to rush it into service.
When the Virginia attacked in Hampton Roads in March 1862, it destroyed several Union wooden ships, but the Monitor arrived the next day for the famous ironclad duel, preventing the Confederacy from seizing uncontested control of the harbor and limiting the damage the Virginia could inflict on the blockade.
After the war, Touvestre continued to live and work in Norfolk’s Black community, drawing on the same drafting and sewing skills that had once enabled her daring act of espionage. The rest of her life remains fragmentary, with local histories disagreeing on her precise origins and path to freedom, but scattered references suggest she remained a respected craftswoman and property owner, quietly supporting her family and neighbors in a city still scarred by conflict and Reconstruction.
Though her name rarely appears in standard Civil War narratives, Touvestre’s quiet act of espionage stands as a powerful example of how an enslaved woman’s courage and technical savvy could shift the balance of a global-scale conflict, even as historical memory has struggled to fully recognize her role. Her single documented act shows how a woman whom the Confederate system sought to render invisible could influence high-level military strategy, and her recovered story stands as a testament to Black women’s strategic brilliance and moral clarity in a nation at war with itself.
If she were alive today, I can imagine Mary saying this: “I was just a seamstress on a long road north, but every step I took with those stolen plans was a step away from the world that tried to own us."
Reflection: What silent resistance have you practiced made a difference—but no one saw it?
Reflection and Action: Journal Prompts for Everyone
Inspired by Elizabeth Key Grinstead? How do you advocate for your rights? Describe a time you stood up for yourself or someone else.
Excited by Mary Richards? How can intelligence and observation be tools for liberation? Write about a time you used your skills to help others.
Loving the story of Mary Touvestre? What would you want Mary to know about our struggles today?
HerStory / OurStory: Journal Prompts for Women of Color
Thinking about Elizabeth Key Grinstead? - When have you taken your fight to court — literally or figuratively? Research a legal case that advanced rights for your community.
Considering the legacy of Mary Richards - How have you operated in disguise? Honor someone you know or know of who used their talents for justice.
Reflecting on the story of Mary Touvestre - How have you used your position, job, or community role as a form of resistance?
Activated Allies: Prompts and Actions for White Friends
For Elizabeth Key Grinstead - Study early colonial Black legal history. Share it when discussing the roots of American law. Learn about early legal battles for freedom in U.S. history.
In honor of Mary Richards - Refuse to let Black women be left out of the stories of heroism. Read about BIPOC spies or intelligence agents in history.
In deference to Mary Touvestre - Center Black women’s roles in wartime resistance. Share their strategic genius, not just their trauma.
What These Women Knew, and What We Must Remember
What links these three Foremothers to each other and to our times is not just bravery, but strategy: they knew how to read the system around them like a codebook and exploited its blind spots—whether that meant turning English common law against colonial slaveholders, performing “invisibility” inside the Confederate president’s home, or carrying stolen naval plans north under the noses of Confederate authorities.
Their lives remind us that even under the worst constraints, human beings can always be thinking, plotting, and imagining their way toward liberation. I love their stories because they were Black women whom history could easily choose to erase (no photos, no portrait, no preserved words) but yet they delivered some consequential blows against slavery and racism. Whether in the courtroom, the parlor, the sewing room, or wherever—we can be supremely spy-tastic.
Thanks for reading this edition of #SistoryLessons, a biweekly newsletter that uses the lessons from Foremothers who led the way as encouragement and guide for these times of resilience. The series is based on stories from my award-winning book, Our Brave Foremothers: Celebrating 100 Black, Brown, Asian, and Indigenous Women Who Changed the Course of History, and other, ongoing research.