As you arrive at the Thomas Day House and Union Tavern in Milton, North Carolina, population 156, a sign instructs you to call “Twinkle.” 

On a Friday morning in June, Twinkle—also known as Vanessa Richmond-Graves—arrives in a 1991 Honda Accord. “Six hundred and four thousand miles, all original parts,” she said proudly. 

A barely contained ball of enthusiasm, Richmond-Graves leads a nonprofit committed to restoring the site and running a community museum. She regales visitors with stories of the town’s most famous resident: acclaimed furniture maker Thomas Day.

The Union Tavern, a simple two-story brick rectangle in the Federal style, once held Day’s workshop on the first floor and his family home on the second. Today, the second floor is off-limits, still unrestored after a fire consumed the building in 1989. A large conference table dominates the main room of the first floor; the nonprofit has been renting the building to the town government, so the museum doubles as town hall. 

Day’s furniture lines the edges of the room. The bureaus that tower over visitors with their dark woods and stately solidity are imposing, but it’s the delicate details—ornate claw feet, sweeping ogee curves—that capture your attention.

The building may be a small, communally run effort now, but it was the height of North Carolina industry and fashion in the mid-19th century thanks to Day’s work. The Union Tavern shop single-handedly produced almost an eighth of the state’s furniture in 1850. When former North Carolina governor and then U.S. Senator David Settle Reid was looking to furnish his plantation on the Dan River, Day was the only man to turn to—47 pieces in 1855 and another 37 three years later. 

A plaque dedicated to Thomas Day stands outside of his old home and tavern in Milton. (Cornell Watson for The Assembly)
Furniture made by Thomas Day inside his former home and tavern. (Cornell Watson for The Assembly)
Vanessa Richmond-Graves, also known as Twinkle. (Cornell Watson for The Assembly)

Day is renowned for his “exuberant style,” as decorative arts historian Patricia Phillips Marshall and architectural historian Jo Ramsay Leimenstoll described in their 2010 book, Thomas Day: Master Craftsman and Free Man of Color.

The pieces he made for Reid, many of which are now part of the North Carolina Museum of History’s collection, are indicative. The scholars praised Day’s work as a “playful interaction of positives and negatives” in which “the viewer’s eye is drawn to the fanciful woodcarvings” before it “quickly fixes on the negative spaces.” A pedestal bureau with carved foliage and sweeping mirror supports is “instilled with motion” that is harnessed “with carefully measured symmetry and balance.”

The descriptions of Day’s work double as metaphors for his life: captivating and elusive.

He has been depicted in turns as a political radical, a boisterous figure of Black pride, a conservative entrepreneur, and a sellout. A free man of color, Day became a wealthy, accomplished businessman and artist in a society that went to war to prove its belief that its Black citizens weren’t worthy of freedom.

But Day didn’t only survive the slave economy—he used it. The 1850 census lists 14 enslaved people working in Day’s shop, home, and farm. At the same time, evidence suggests Day had ties to abolitionists, and many believe his slave owning was nothing more than cover to survive a world that targeted men of his race. That evidence, however, is contested, and neglect of African American history in archives and academia leaves the accounting of Day’s life incomplete.

An example of Thomas Day’s woodwork. (Cornell Watson for The Assembly)

For decades, it fell to women like Richmond-Graves to nurture instead. A lifelong Milton resident, Richmond-Graves grew up back when the town had a general store and a mercantile selling hoop cheese and penny candies. She was a curious child who used to spend afternoons with the town’s unofficial historian, a white teacher named Mary Satterfield.

“She would just tell my dad, ‘Earl, leave Twinkle with me for a little bit. I want to tell her more about Thomas Day,’” Richmond-Graves remembered. “About 11 or 12, she told me, ‘One day, you’re going to be talking to people from all over the United States, and maybe abroad, about Thomas Day.’ Of course, at 12, I’m going, ‘Yeah, right.’ But she prophesied that, and it’s true.”

As Day’s reputation grew to include collectors and museums, it attracted more scrutiny from the professionals. While Richmond-Graves is an avid believer in Day the abolitionist, Marshall and Leimenstoll downplayed those ties in their book. They present him as a profit-maximizing businessman, through and through.

Inside Day’s home and tavern in Milton. (Cornell Watson for The Assembly)

Released in conjunction with a 2010 exhibit at Raleigh’s North Carolina Museum of History that Marshall curated, the book was the high-water mark in Day scholarship. It also demanded proof that volunteer community historians couldn’t readily provide. Perhaps no one could. 

Many Day devotees are still harshly critical of the book and exhibit, both because of the interpretive disagreements and because of what they see as other inaccuracies. Even a statue of Day at the Museum of History is an invention: There aren’t any known photographs of him, so the likeness is merely an artist’s interpretation.

In July 2022, the General Assembly provided $800,000 for the state of North Carolina to turn Day’s workshop into a state historic site, and Gov. Roy Cooper’s 2023-25 budget proposal included another $4.8 million. But the sale of the property is not yet final. Once it is, the story of Thomas Day will be told by state employees and bureaucrats rather than devoted community volunteers.

As the teaching of Black history has become a hot-button issue within and beyond North Carolina, so too has the effort to tell the complicated story of Day’s unique life. Whether we see Day as a hero, villain, or something in between becomes a test of whether we can confront the complexities of American racism. 

The Man and the Town

When the first retrospectives about Day were published in the early 20th century, his story was still largely myth and legend wrapped up in Jim Crow racism.

In a 1928 issue of Antiquarian, journalist Caroline Pell Gunter wrote that Day “possessed a fine physique and had the manners of a Chesterfield,” that he was a believer in slavery, and that he reinvigorated a lagging workshop by singing Thomas Carlyle lines with a “melody that belongs peculiarly to the Negro race.”

Church pews made by Thomas Day are still installed inside of a church downtown Milton. (Cornell Watson for The Assembly)

“An earlier article on that unusual character, Tom Day, once of Milton, brought to light a great deal of new material which clarifies some of the dark points,” another journalist, Paul Ader, wrote in a 1941 issue of the Greensboro Daily News. “In families all over North Carolina, we learned, there is still furniture which was carved by the brown hands of this native West Indian. Still shrouded in mystery is the origin of Tom Day.”

Day was in fact a tri-racial man and not West Indian at all. He was born in Virginia in 1801. 

His father, John, had been born to a white South Carolina woman who had an affair with her Black coach driver. He was sent to live with a Rowan County family of Quakers—a religion with a storied history of anti-slavery activism in North Carolina—and trained as a cabinetmaker. As an adult, John Day settled in southern Virginia and married Mourning Stewart, daughter of a prominent doctor of white, Black, and Native American ancestry who owned nearly 900 acres of land and at least 16 slaves.

His knowledge of a skilled trade was a rarity for free Black men at the time and allowed John to provide a decent life for his children—though his older son, John Jr., described his father’s “intemperate” nature as a cause of family turmoil. Both John Jr. and Thomas trained in their father’s shop, and the younger son set off on his own in the early 1820s, first to Hillsborough, then to Milton, in Caswell County. Thomas settled there, marrying Aquilla Wilson, a free Black woman from Virginia, in 1830. Together they raised three children: Mary Ann, Devereaux, and Thomas Jr.

Milton was something of a boomtown. Positioned near the Dan River at the Virginia border, it was a crossroads for transporting agricultural goods—particularly tobacco. As their wealth grew, Miltonites wanted to furnish their homes in the newest styles, and Thomas was there to provide it. He offered goods made from exotic hardwoods, like imported mahogany, as well as cheaper pine, attracting a diverse group of customers. He even sold coffins. 

Another example of Day’s work. (Cornell Watson for The Assembly)

Much of Day’s surviving furniture adapted Federal and Greek Revival styles, but he made his mark by adding his own twist to the scrolls and detailing. As his clients became more successful, they offered him more design freedom. He added architectural details to new plantation estates that included mantels, built-in shelves, and banisters.

Day’s interpretations became a unique style. It was a kind of folk art featuring curving, organic shapes that Phillips and Leimenstoll deemed “a precursor to the sensual designs of the Art Nouveau style almost forty years later.”

Economic success followed stylistic innovation. Day’s customers included prominent businessmen like Reid and the University of North Carolina. The latter chose Day to build library shelving in Old East and Old West, two recently renovated, prominent buildings in the center of campus, even though his $293.25 bid was $100 more than the others the university received. 

“For my justification to him and to the Trustees, I must rely upon the superior manner in which I expect you to execute the work,” university president David Swain wrote to Day in 1847. “For the present you must not mention to anyone the amount you are to receive.”

As his success grew, Day accumulated land—270 acres, more than half of which was used to cultivate “tobacco, wheat, Indian corn, oats, and sweet potatoes,” according to Marshall and Leimenstoll. In 1848, Day was able to purchase the Union Tavern in the middle of downtown Milton, turning the former watering hole into his home and workshop. A few years later he added a steam engine, mechanizing his production lines. By 1855, Day’s net worth was estimated at $40,000, the equivalent of roughly $1.5 million today.

But within a few years, Day was bankrupt.

Financial panic swept the country in 1857, and the planters who made up the bulk of Day’s customers couldn’t pay what they owed him. He in turn couldn’t pay his own debts. 

Day could have used his immense wealth to move his family out of the South and to a free state long before the boomtown went bust. But segregation was the norm in the North’s urban cities, and he would face discrimination and increased competition. “For such skilled free Negroes, migration often meant a sure loss of economic status,” historian Ira Berlin wrote in his seminal 1974 study of free Blacks, Slaves Without Masters.

Why they remained is an open question. Day’s obituary gives no hints, because none has ever been found. All that is known is that he died sometime in 1861.

A Dangerous Time

While Day’s business still flourished, the number of free Blacks in North Carolina was small—roughly 3 percent of the state and only 10 percent of the Black population. 

But they played an outsized role in the imagination of slavery’s proponents. Their population had grown nearly 300 percent between 1800 and 1850. Slaveholders were terrified of the psychological impact this would have on those they kept in bondage.

A series of high-profile national events also led North Carolina’s plantation elite to come after free Blacks: Denmark Vesey’s attempt to launch a slave revolt in Charleston in 1822; Vermont’s passage of a resolution calling for the national abolition of slavery in 1825; and the publication of David Walker’s Appeal, a famous and incendiary abolitionist tract, in 1829. Walker was a North Carolina-born free Black man, to boot.

The North Carolina General Assembly passed new laws making it harder for slaves to be freed and limiting the freedoms of Black residents who were already free: requiring some of their children to be bound out as apprentices, forcing every able-bodied adult to work, prohibiting them from playing games of chance with slaves, requiring them to obtain a license to travel outside of their counties, and outlawing marriage between whites and free Blacks.

In 1826, the General Assembly passed a law making it illegal for free Blacks to move to North Carolina, which became a central act in Day’s life story.

A plaque highlight’s the site’s significance as a National Historic Landmark. (Cornell Watson for The Assembly)

When Day married Wilson in 1830, the law barred her from joining him in Milton. Faced with the prospect of losing a skilled artisan, 61 of Day’s white neighbors—including State Senator James Kerr, both Caswell County state representatives, and a number of well-to-do businessmen—signed a petition requesting that the General Assembly grant Day’s new wife an exception to the law. Day, they wrote, was “a first rate workman, a remarkably sober, steady and industrious man, a highminded, good and valuable citizen.”

On New Year’s Eve 1830, the legislature passed “an act to authorize Aquilla Day, otherwise known as Aquilla Wilson, a free person of colour, to reside in this state.”

Aquilla was not the only person granted an exception. Many defenders of Black bondage were loyal and supportive when it came to Black people they knew, even going so far as to free their own slaves while making it harder for others to do so. 

“The way I’ve tried to explain it in my own work,” historian Warren Milteer Jr. told The Assembly, “is that there are other things that white people, or at least some white people, cared about in addition to or besides race.” For some, this opened up opportunities. For others, it created more oppression, he said: “Like if you’re a free person of color and you’re poor versus being Thomas Day.”

The antebellum South was not a simple Black/white binary, Milteer says, but a complicated web defined by race, class, gender, family, and other factors. There wasn’t a single Black experience.

“A South with white people on top and people of color at the bottom is much less complicated than a social landscape in which various forms of hierarchy intersect,” Milteer wrote in Beyond Slavery’s Shadow. “However, we must abandon this simplified version of the South in order to comprehend more fully the historical experiences of the southern population in all its diversity.”

The vast majority of free Blacks were destitute and propertyless. Day’s wealth placed him among the richest men of any race in Caswell County and made him an anomaly within an anomaly.

But growing closer to the white elite often meant wealthy free Blacks grew away from others of their race. Even poor free Blacks were generally more conservative than the enslaved, as they had more to lose, Berlin wrote. That was even more true for the rich: “Status differences continually eroded the bonds of racial unity and turned free Negroes and slaves against each other.” 

Day was skilled, intelligent, wealthy, and educated, and the white elite identified with that. Leveraging that trust, Day was able to carve out an unusual amount of freedom.

The Days also belonged to a white church just a few doors down from their home in the Union Tavern. Thomas built the pews, and the accepted story is that he did so in exchange for the right to sit among the white parishioners. Their slaves remained in the balcony.

When Thomas and Aquilla were formally accepted as full church members in 1841, “no notation of race was placed beside their names” in church rolls, Marshall and Leimenstoll noted.

Historian John Hope Franklin, who helped popularize Day’s story with his 1943 book The Free Negro in North Carolina, 1790–1860, wrote that he was one of the “capitalistic-minded free Negro owners of slaves.” 

Day, he wrote, was among the “individuals who were not only satisfied with their own position but with the general structure of North Carolina society as well.”

Opposing Views

Milton locals have long rumored that Day had a secret life. Some even claimed his workshop was a stop on the Underground Railroad. But without any corroborating evidence, historians ignored the claims. 

Filmmaker turned Day aficionado Laurel Sneed helped change that.

As a young white woman in segregated Goldsboro, race was a mystery to Sneed. She couldn’t fathom why she would wait in line at the white water fountain when the colored one was open, she says. In Day, she found a person and a story that seemed to ask many of the same questions.

In 1995, Sneed and her husband launched the Thomas Day Education Project, aiming to create materials about Day and others for public schools. Now in her 70s, Sneed hasn’t stopped. 

Laurel Sneed, a Thomas Day researcher, in her home library in Goldsboro. (Cornell Watson for The Assembly)

That project grew into the Crafting Freedom Institute, which creates K-12 materials about Black history more broadly, and Sneed has enlisted Chris Everett, producer and director of the documentary Wilmington on Fire, to produce a film about Day.

Franklin had served as an adviser to one of Sneed’s early Day research projects, and she originally adopted his view of him as an opportunist. “Any whiff of abolitionism—I didn’t take that seriously for 15 years,” she said. “Any Black site, there’s always this rumor that it was an Underground Railroad site.”

Sneed and her coauthor, former Washington Post writer Patricia Dane Rogers, published about Day for years and show up in the footnotes of just about every publication about him from the past few decades. But in 2009, a key piece of evidence changed Sneed’s mind about Day’s views on slavery.

Sneed and Rogers revealed that Day’s name was among the attendees of the Fifth Annual Convention for the Improvement of Free People of Colour in the United States, held in Philadelphia in 1835—a much more radical act than Franklin’s Day would have considered.

But while it’s clear that a Thomas Day attended the 1835 conference, some argue it wasn’t the one from Milton but one of the five other Thomas Days listed in North Carolina census records from the time. 

“Thomas Day would have been committing suicide to have gone to that convention in Philadelphia,” said Earl Ijames, the North Carolina Museum of History’s curator of African American history and a member of the exhibit’s advisory committee.

The historian Milteer, also a member of the exhibit’s advisory committee, believes the man who attended the convention was likely the famous furniture maker. But he doesn’t believe that proves Day was secretly an abolitionist.

The convention covered a broad range of topics that “were actually pretty bourgeois,” Milteer told The Assembly, including “medical school for people of color, the promotion of science, and sugar production.” (Marshall and Leimenstoll point out that another topic was the need to investigate Black slave owners.) 

The convention delegates also included supporters of the colonization movement, which viewed abolition as too radical and instead aimed to separate the races by moving all Black people out of the country. Many out-and-out white supremacists supported that idea as well. Day’s own brother, John, left for Liberia with the American Colonization Movement in 1830 and became one of the country’s founding fathers.

After the discovery about the Philadelphia convention, another complicating detail about Day’s life took on new meaning for Sneed: He sent his children to the Wesleyan Academy in Wilbraham, Massachusetts. The school was home to a number of anti-slavery teachers and students, including the principal, Miner Raymond, who was once described as a “flaming abolitionist.” 

But many racist white slave owners also sent their children to boarding schools with abolitionist ties, notes Milteer—some with even more well-documented radical reputations than Wesleyan. 

To Sneed and her allies, it’s not hard to see why a Black man would have kept his political leanings secret in the lead-up to the Civil War. The way she sees it, the fact that people like politician Romulus Saunders thought Day would support the white planters in the midst of a slave uprising, as Saunders once claimed, is not proof that Day identified with his class over his race but a sign of his talent at navigating slave society.

Others think Day is worth celebrating even as a slaveholder. Ijames points out that the people Day owned gained skilled trades most slaves never had access to, and that he likely treated them better than a white owner would have.

Ijames says Day deserves to be remembered for his “business acumen and his genius” that allowed him to run a workshop that included slaves, free Blacks, and white journeymen.

“He’s actually creating a model business culture in the antebellum South that people strive for today to maximize output and productivity,” Ijames said.

Keeping a Legacy

Carolyn Green Boone pulls up a Facebook video on her phone as we sit in a Durham coffee shop.

“Historians and speculators, stop talking about my great-great-great-grandaddy and let the man rest in peace with his amazing and magnanimous legacy intact,” she says in the clip, recorded at the opening of a Thomas Day exhibit at Preservation Greensboro’s Blandwood Museum in April 2022. “Great-great-great-grandaddy was a rescuer of people of color, and those people who were his so-called slaves were living under his shelter.”

Carolyn Green, a descendant Thomas Day, stands beside a statue of him in Raleigh. (Cornell Watson for The Assembly)

Boone has often been called upon to represent Day’s descendants at public events. Her pride is clear. Her Durham home is across the street from North Carolina Central University, a school founded by her great-grandparents James E. Shepard and Annie Day—Thomas’s granddaughter.

“All I can do is put myself in his position as a free person of color and ask myself what would I have done,” Boone said. “I would have played whatever role I had to play to stay alive and keep myself and my family safe. And I would have just tried to bring as many people as I could under my umbrella of protection.”

Even, she said, if that meant buying enslaved people.

For Boone, the historical debates over whether there is adequate documentation of her family history are beside the point. 

“It was literally against the law and the threat of peril or death for someone to know how to read and write,” Boone said. “You have this whole culture of people who were under those circumstances for hundreds of years and then you try to invalidate their history by saying, ‘Oh, it’s oral, it’s not written down?’”

That so much of Black history is not well documented is part of what makes what happened to Day’s Union Tavern even more tragic. Day’s work is the rare, documented, material piece of antebellum Black history that can be touched. But in 1989, fire gutted the home and workshop. 

Twinkle Richmond-Graves and other Milton citizens scraped together grant money and donations to save it. Even then, Richmond-Graves knew she needed to consider how people respond to Day’s complications.

“When we’re giving tours, I can pretty much read who will not believe it and who will believe it,” she said. “You just feel the vibes: ‘No, don’t go there, Twinkle, turn it around a different way.’ They want to hear what they want to hear.”

Some of those people are white tourists clinging to a Gone With the Wind mythology of the South. Some are Black people who can’t comprehend Day’s actions. 

To Anica Green, another Day descendant, the abolitionist version might just be its own kind of comforting narrative.

“I think a lot of Black, well-to-do, cis-het people tell themselves a lot of convenient lies to make themselves feel comfortable with their position in society and not challenge the status quo as much as it would take to lift everyone up,” Green said.

A Durham native, the 27-year-old musician, artist, and creative consultant says they didn’t know much about Day until recently. It was only after graduating from Brown University, where their privileged upbringing became clear, that Green first heard the stories. They identify as an anti-capitalist and wrestle with Day’s story.

The outside of the Thomas Day home and tavern in Milton. (Cornell Watson for The Assembly)

Soon it will be the North Carolina Department of Natural and Cultural Resources that determines how Day’s story gets told, once the purchase of the Union Tavern is finalized. The budget passed last week includes $4 million for developing the site. 

This new era comes with more funds, but it is not without risk. Republicans in the General Assembly recently passed a law restricting how Black history can be taught in public schools, and the House passed another requiring a history class with a reading list lawmakers will determine. (It stalled in the Senate.)

Michelle Lanier, the director of state historic sites and properties, said she is not concerned about the current political climate: “If I invest time and energy in being afraid, I simultaneously divest time and energy from focusing on the good work.”

Lanier has described her work as aiming to “amplify the silenced narratives” and often talks about the importance of partnering with the community to tell more nuanced stories—stories like Day’s.

“I am not interested in telling stories based on valorizing a person,” Lanier said. “I’m interested in telling stories of human beings, and all human beings are complicated.”

But others are worried about the state’s track record. “Each generation, there’s a new iteration of this stuff,” said Peter Wood, an emeritus professor at Duke University who has collaborated with Sneed and the Crafting Freedom Institute and was an inaugural board member of Durham’s Historic Stagville. 

“Who writes the history makes a difference,” he said. “Who controls the history museum makes a difference. … All those things get fought over, and the boys with the bowties get put in to run these things.”

And in the case of Day, the complications of his life reflect many of the same complications we’re still dealing with today.

“We don’t do ourselves favors and we don’t grow by trying to look away from what might be ugly,” Green said. “But we also don’t do ourselves any favors by black-and-white thinking.”

Matt Hartman is an Assembly contributing writer based in Durham. He’s also written for The Ringer, Jacobin, The Outline, and other outlets.

More by this author