Why Was Robert Webster, a Slave, Wearing What Looks Like a Confederate Uniform?

This remarkable man risked his life to undermine the Confederacy yet remained close to his former owner after the Civil War

In this portrait, Webster wore what looks like a Confederate uniform, but there is no evidence he fought for the South. (Julie Rowlands Collection)
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As Confederate troops abandoned Atlanta during the night between September 1 and 2, 1864, they blew up a stranded 81-car train packed with munitions. A series of explosions, audible 80 miles away, leveled nearly everything within a quarter-mile and set the cotton warehouses aflame. The perplexed Union commander, Gen. William Tecumseh Sherman, said that from his position almost 20 miles distant, the sound of the fire was “like that of musketry.”

Yet when a few hundred stunned people clustered downtown on the morning after, one of them remarked, “I have never seen the city more quiet.” After living under siege for nearly six weeks, they watched nine of Atlanta’s leading citizens saddle up to ride out to surrender the city to Sherman’s 100,000 men. “Language falls short,” one of those on hand wrote, “in expressing the suspense and anxiety experienced by everyone.”

Perhaps the clearest signal that life in Atlanta would never be the same could be seen among the men who rode out under the white flag: One of them was black. And while technically still a slave, he was as rich as the white men riding beside him. “[He] was better off than any of us,” a white businessman would testify. Bob Yancey, as he was known at the time, was 44 years old. Over the course of his life he was also called Bob, Bob Gadsby, Bob Cunningham, Yancey and, finally, Robert Webster. After the war, he would insist that Webster was his rightful surname—a legacy from the famed Senator Daniel Webster, whom he claimed as his father.

A newly surfaced photograph, published here for the first time, gives a good idea of what he looked like: round of face yet square of chin, with dark, widely spaced eyes that seemed to hold a melancholy gaze. The portrait, which measures just 2 3⁄4 by 3 1⁄4 inches, is what is known as a sixth-plate ambrotype, a positive image on a glass plate reduced to one-sixth its normal size. Most surprising, it shows the slave wearing what appears to be a Confederate Army shell jacket.

Images of African-American men in Confederate uniform are among the greatest rarities of 19th-century photography: Only eight were known to exist, according to Jeff Rosenheim, curator of the 2013 exhibition “Photography and the American Civil War” at New York City’s Metropolitan Museum of Art. The portrait of Robert Webster adds a ninth to that roster. Such images, says John Coski, vice president and director of historical research at the Museum of the Confederacy in Richmond, Virginia, are “tantalizing in what they do and do not tell us.” One thing they don’t tell us, he says, is that the men in the photographs fought in the Confederate Army, contrary to the belief of some researchers eager to show that African-Americans did so. Of the slaves photographed in Confederate uniform, the names and fortunes of only four are known. All four went to the front as servants to their owners, who were Confederate officers.

Robert Webster went to the front in Virginia in 1861 with Benjamin Yancey Jr., an enormously wealthy planter, lawyer and sometime politician who owned scores of slaves scattered among several houses and three plantations, including one in Georgia that covered more than 2,000 cultivated acres and another of 1,000 acres in Alabama. Yancey owned Webster for almost 20 years, and valued him highly. “I would have trusted him with anything,” Yancey said in later years. Indeed, after he became alarmed about Federal threats to the lower South, Yancey sent his wife and three children with Webster back to Alabama, where the slave was to “boss the plantation in his absence,” according to Yancey family lore. Yancey didn’t stay long in the fight, though, returning home in the spring of 1862 to oversee his plantations himself. With itinerant photographers often accompanying troops, the Webster portrait was in all likelihood made while the slave was in Virginia.

It has remained with Yancey’s descendants through five generations. Representatives of the family told me about it after I published The Bonfire: The Siege and Burning of Atlanta, my 2009 book, in which Webster played a prominent role. Yancey’s great-great-granddaughter Dorothea Fink says she remembers seeing the portrait on her grandmother’s mantel beside other family photographs and memorabilia. It is the only portrait of a slave the family displayed, she says. “It was kept in an esteemed place,” she says her grandmother told her, “because he became a very important person to the family.”

In fact, Webster’s importance to the Yanceys extended far beyond his wartime service, even though there is no evidence that he fought for the Confederacy and ample evidence that he risked his life to undermine it. One thing the portrait tells us is that Webster learned to manage conflicting loyalties while helping to liberate himself. From start to finish, his life reflected the complications that accrued from slavery and the precarious, contingent and dangerous position of slaves during the Civil War.

"I would have trusted him with anything," said Benjamin Yancey, Jr. (left, in his Confederate uniform), who owned Webster for 20 years and took him to the front in Virginia as a servant. Webster claimed Daniel Webster (right) as his father, and a Senate doorman recalled that the young man often visited the imperious Massachusetts politician. (Julie Rowlands Collection; Library of Congress)
Webster was raised in the slave quarters at the National Hotel in Washington, D.C., but he developed a keen sense of commerce. A white Atlanta businessman said he was "about one of the biggest traders we had here." (Library of Congress)

Little is known about the lives of individual slaves, but historians have filled in many of the blanks in Robert Webster’s life, drawing on contemporary diaries and newspapers, property manifests and postwar testimony by friends and neighbors before Federal commissioners adjudicating property claims. Thomas Dyer, a now-deceased University of Georgia historian who did yeoman spadework on Webster’s background, described him as “half-slave and half-free, neither black nor white.”

He was born into slavery in Washington, D.C. in 1820, and grew up with his mother and siblings in the slave quarters of the National Hotel, the capital’s most opulent hostelry. The limestone-and-brick building, now gone, stood five stories tall and nearly filled a city block on dusty, bustling Pennsylvania Avenue. (It wasn’t far from Ford’s Theatre; John Wilkes Booth took a room there in the days before he assassinated President Abraham Lincoln.) Like his mother and siblings, Bob, with no surname, was the property of National owner John Gadsby. Daniel Webster, the famed orator, Massachusetts senator, secretary of state and presidential candidate, was a frequent visitor and sometime guest at the hotel.

The senator was no man to trifle with; he could be impatient and imperious to the point of cruelty. Along with his booming voice, his appetite for food and drink were legendary. Tall, and with a domed forehead fringed by black hair, he always dressed in a black suit, and a contemporary said his dark eyes burned “almost superhuman.” Even his colleagues found him terrifying. But Isaac Bassett, the era’s longtime Senate doorman, recalled the temerity of a “coloured boy” who knocked at the Senate Chamber doors and asked to see his “father” sometime in 1832. Afterward, Bassett wrote, Bob “freekently [sic] came up to the Senate Chamber to see Senator Webster.”

Rumors of sexual improprieties dogged the senator during his lifetime and after. In 1850, Jane Grey Swisshelm, the first woman to report from the Senate Press Gallery, was so enraged at Webster’s support for the Fugitive Slave Act—which required the capture and return of escaped slaves even from states where slavery was illegal—that she alleged in the Pittsburgh Saturday Visiter that he was keeping mistresses, “generally, if not always, colored women.” In a memoir, she wrote that he had fathered “a family of eight mulattoes” in Washington, “bearing the image and superscription of the great New England statesman.” Modern biographers acknowledge that the senator was notorious for what the antebellum South Carolina politician James Henry Hammond called “loose indulgences with women,” but no documentary evidence confirms Swisshelm’s account.

Robert Webster was the only African-American to claim publicly that the senator was his father. Around 1879, he told a reporter for the Chicago Times that his mother “talked freely to him of his origin, and told him many anecdotes of the private life of Mr. Webster to whom she was passionately devoted.” The reporter saw a “striking” physical resemblance to Daniel Webster, though he had been dead since 1852. “His broad forehead and widely separated eyes are noticed as circumstantial proof as soon as you hear the story of his birth,” he wrote.

Robert Webster said the senator brought his mother to Massachusetts at some point and “gave her perfect freedom, though she continued to be a housemaid in his home.” But young Bob would have been long gone from the nest: When he was around 20 years old, the innkeeper Gadsby gave him to his son as a personal servant, and the son promptly lost him in a poker game. The winner auctioned him away, and Bob was shortly enslaved at Rosemont, a plantation outside Greenville, South Carolina. There he met Benjamin Yancey, a lawyer who helped manage Rosemont.

Decades later, Yancey would recall Bob as “a very intelligent and accomplished house servant.” He noted his skills with meats and pastries, as well as his “fine” way with preserves and pickling, and said he was “a good barber.” After six years at Rosemont, the slave persuaded Yancey to purchase him and his wife. When Yancey—who didn’t really need any more slaves—consented, he set one condition: Bob would have to give up “card playing,” which he was apparently exceedingly fond of. He did, though he would make his affinity for gambling pay off in other ways.

Yancey quickly came to think of his new slave as “truthful, sober, affectionate, honest....He was a faithful servant, much attached to me, my wife and children.” His confidence in Bob grew to the point where he had him “training up under him several young favorite negroes.”

In 1858, President James Buchanan dispatched Yancey to a diplomatic post in Argentina. In departing, Yancey set Bob up as a barber in Atlanta in return for a monthly rent payment. “I gave him practical freedom and the means of making and using money,” Yancey said.

Webster soon had two shops and seven barbers working for him, but he made most of his money through loan sharking, lending money at exorbitant rates to players in the nonstop card game he ran out of one of his shops. He made enough money to buy a house on a hill overlooking downtown, though the deed was assigned to Yancey because, by law, slaves could not own property.

Before the Civil War, Yancey returned from Argentina and took up residence in Atlanta. It was a small, rough railroad junction and regional market town, but once hostilities broke out, it became an instant city. The factories that had served the railroads began to turn out armaments and munitions, uniforms and armor plating. Refugees fleeing the fighting in Tennessee and on the East Coast jammed the red clay streets, as did soldiers on their way to the front and their wounded brethren headed for the city’s overflowing military hospitals.

Robert Webster found opportunity in the chaos. He began to speculate in currency and gold. As a barber and a slave, he could pass without suspicion among Union captives awaiting transfer to prison camps such as Andersonville, 125 miles south. The Yankees were eager to trade Union greenbacks for Confederate notes they might use to buy food or clothes—or to abet their escape. Though it was illegal and dangerous, Webster traded those paper U.S. dollars with his Atlanta neighbors, sometimes getting as many as 300 Confederate dollars for one greenback. According to a white Atlanta businessman, Webster once showed him two $1,000 Federal bills, for which he had paid Union soldiers a paltry $8,000 in Confederate money.

With those funds, he bought the equivalent of a small warehouseful of goods and produce, including tobacco, which was greatly prized amid wartime scarcity. Even as the war crushed the fortunes of many white neighbors, Webster got richer. “I never made less than $100 a day,” he swore in later years. “No man in the place stood higher than I did, although I was a colored man.” Another white Atlanta businessman said Webster had money, gold and gold watches “always about him.” Despite the risks, financial and legal, he was “about one of the biggest traders we had here.”

At the same time, Webster proved to be one of the North’s best friends in Atlanta, according to sworn testimony by other Unionists in town. “Mr. Robert Webster was one of the 35 or 36 loyal men of the city during the war,” said a white loyalist who was among those who knew Webster best in those years. “He was heart and soul a Union man,” another proclaimed.

Known Unionists faced harassment and, if they were caught acting on their sympathies, far worse. Yet Webster likely provided a rope that enabled a loyalist leader to escape from an Atlanta prison barracks. He also hid two escaped Union soldiers in his attic until their comrades arrived. And he may have done his greatest service to the North after the carnage of the Battle of Atlanta on July 22, 1864.

Hundreds of wounded Union soldiers—many of them with shattered limbs, maggot-ridden wounds or gangrene setting in—were left in an open field in the city center, where they moaned and writhed for two days under the blazing sun without food, water or medical treatment. Townspeople, fearing angry and heavily armed Confederate troops chasing through the battle-ravaged city, dared not help the wounded enemy soldiers.

Webster “took charge of the whole matter himself,” one eyewitness testified. He brought water to the parched men lying on the ground and bandaged wounds. He offered money to buy food and paid other black people to help. Before long, more slaves joined him, and soon “all the colored people did the same thing,” said one of those who pitched in. Webster organized teams to carry wounded Yankees to a hospital space opened to them. “Many of the wounded would certainly have died if it had not been for the attention of these men,” a white witness testified.

After the Confederates surrendered Atlanta, Union troops occupied it for two and a half months, during which foragers took whatever they could use to support the troops—including Webster’s store of goods, produce, livestock and, most valuably, tobacco. “My Lord,” he cried to a neighbor, “I thought they had come here to protect us, but they have taken everything I have got.” His efforts to claim $10,000 in compensation from the United States, which led to the testimony Webster’s friends gave to the Federal government’s Southern Claims Commission, went nowhere. But despite losing much, he managed to hide at least some of his wealth.

Benjamin Yancey was not so fortunate: The war left him with four horses, burned-over land and demolished farm buildings. With his slave wealth gone, he was destitute. At that point, Yancey turned to Webster, writing to ask “if he could loan me $150.” He said his former slave replied with one hundred dollars in gold and another hundred in silver, along with “word that I could get more if I wanted it.”

With Webster’s help, Yancey restored his bank credit. He hired freedmen to rebuild his plantations, and he cultivated cotton, corn, wheat and other crops. Living on his estate in Athens, he served as president of the Georgia State Agricultural Society from 1867 to 1871—years in which he championed the modernization of Southern farming and the restoration of the planter class. Prosperous once again, he later served in the Georgia legislature and as a trustee of the University of Georgia. He remained a grandee until he died, in 1891, at age 74.

The postwar era promised Webster something similar—at first. He ran what an Atlanta newspaper now termed his “famous” barbershop and became a Republican Party stalwart, “known to nearly every politician in the state.” When Georgia moved its capital from Milledgeville to Atlanta in 1868, he reached into his own pocket to house and support newly arriving black politicians. But the old order reasserted itself once Reconstruction gave way to Jim Crow in the late 1870s. At some point, Webster began to drink, and his trading and barbering businesses failed. In 1880, he wrote (or a scribe wrote for him) to Yancey, addressing him as “My old master and friend”: “Pleas [sic] give me a start in this World once more,” he begged.

Yancey’s response is not recorded, but a newspaper reported later that Yancey provided for Webster, his wife and their daughter, ensuring that after his former slave died, in 1883, at age 63, his widow and daughter still had a place to live.

Yancey never forgot Webster’s devotion, and the ambrotype portrait ensured that his descendants wouldn’t either. From Yancey it was passed to his eldest daughter, and from her to Yancey’s granddaughter, and from her to his great-grandson, and then to his great-great-granddaughter. Yancey’s great-great-great-granddaughter Julie Rowlands has it now; she keeps it on display in her home in northern Ohio. “I consider him to be a relative, even though not by blood,” she says.

For his part, Webster made his feelings clear. In a letter to the Atlanta Daily Constitution in 1879 protesting an article that called him “Bob Yancey,” the one-time slave wrote, “My name is and has always been Robert Webster, though I love the noble name of Yancey.” More than a century and a half after his glass plate image was made, that struggle to establish his true name and his portrait in Confederate garb reflect the enduring paradoxes of slavery, the unbroken bond of two men—one master, one slave—and the complexity of their intertwined American lives.

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