Fugitives or freedom seekers? What the Grayson sisters’ escape means today

NEBRASKA CITY, Neb. (CN) — On a frigid night in 1858, sisters Celia and Eliza Grayson slipped across the Missouri River from Nebraska to Iowa on a small flat-bottomed boat.

They were following the Underground Railroad as they escaped the home of their enslaver in Nebraska City, a then-new town in Nebraska Territory.

The sisters made it to Chicago, where an effort to abduct Eliza Grayson back into slavery made national headlines and nearly sparked a riot.

"The threat of violence between the hired goons capturing freedom seekers and the communities that protected them hung over the city,” historian Jeff Nichols wrote last year during a surge of federal immigration agents in the Windy City.

Today, the Grayson sisters’ escape has been largely forgotten.

Little evidence of the saga remains in Nebraska City. The house of their former enslaver is long gone, though there is a park named after him near downtown.

The place where the Graysons embarked — Wyoming, Nebraska — is also long gone. The Missouri River has been rerouted by about a mile, and the natural pier that the sisters likely used no longer touches the water.

Local landowner Jim Johnson will sometimes show curious visitors around. This was an important stop in American history, not just for the Underground Railroad but for Mormons heading west.

From behind the wheel of his pickup truck as he drove across his property, Johnson pointed out landmarks, including old roads and the since-closed Wyoming cemetery. 

He shook his head, noting the lack of public curiosity about a part of history that was really not so long ago.

“It’s history. We learn from history, and it’s so interesting if [we] take the time to learn it,” Johnson said. “It’s fascinating what people had to do to survive in [that] day and age, and the trials and tribulations that they experienced.”

Also in the cab was Gail Shaffer Blankenau. A Nebraska historian, she’s written extensively about the Grayson sisters, including for a 2022 article for Nebraska History magazine and a nonfiction book in 2024. That book, “Journey to Freedom: Uncovering the Grayson Sisters' Escape from Nebraska Territory,” won a Nebraska Book Award last year for nonfiction history.

As the Grayson sisters headed toward the promise of freedom, their pursuit by their former enslaver received full support from the federal government. The search was violent, inflicting property damage and injuries on those who stood in the way.

It’s not hard to see why some might draw parallels with current immigration enforcement — but any comparison between clear historical wrongs and present-day news stories will naturally be controversial. For her part, Blankenau strongly pushes back on this analogy. Instead, she says the Grayson sisters’ story makes her think of the scourge of human trafficking.

Stopping at rest stops along Interstate 80 in Nebraska, she noted that she often sees posters from the Nebraska Department of Transportation providing an emergency number for victims to call.

“They are being held in a form of modern-day slavery,” she said. “I do think of Celia and Eliza sometimes when I look at those signs.”

While Cornhuskers may like to think of their state as anti-slavery, at the time there was heated debate over whether the practice should be allowed.

The Graysons’ enslaver, Nebraska founding father Stephen Friel Nuckolls, naturally hoped to see Nebraska become a slave state.

For those who need a refresher on this era of American history: The Kansas-Nebraska Act of 1854 opened Kansas and Nebraska to white settlement, with the new settlers allowed to decide if each territory would become a slave or free state. Settlement of this region thus became at least partially an ideological battle over whether the United States would become predominantly free or predominantly slave-owning. Both pro- and anti-slavery settlers moved into Kansas, leading to a period of violence now known as “Bleeding Kansas.” Nebraska did not see conflict at anywhere near that scale. 

Originally from Grayson County, Virginia, Nuckolls and his family moved to Nebraska in 1854.

Nuckolls founded Nebraska City and brought the first slaves into the state: the Grayson sisters. Historians believe they’re named after Grayson County where they were born.

Nuckolls quickly became a local power player, establishing a chain of general stores and getting elected to the legislature. 

He was “a person of some charm,” Blankenau told Courthouse News. And yet even to other white people, Nuckolls could be a brutal and frightening figure. As Blakenau puts it: “He obviously had a temper, and he obviously hated abolitionists.”

“They called the Nuckolls brothers ‘the indomitables,’” Blankenau said. “That tells you a little something about his character.”

The Grayson sisters worked as servants in the Nuckolls family’s large brick home on Main Street, now known as Central Avenue.

When Stephen Nuckolls’ parents died in 1857, it raised the possibility the sisters would be sold and relocated, as often happened upon the death of an enslaver. That could mean being split up and moved to nightmarish conditions in the South.

But there was also opportunity: With Nebraska Territory on the frontlines of the slavery debate, abolitionists were also moving there. The Underground Railroad skirted Nebraska City before crossing the Missouri River into free-state Iowa. Getting into contact with someone willing to help them escape would be far from impossible.

On the night of Nov. 25, 1858, the sisters slipped out of the house. 

A free Black Cherokee man named John Williamson guided them to Wyoming, Nebraska. The sisters boarded a boat — a risky journey, considering the river was dark and icy. “A lot of people died crossing the Missouri, even in good weather,” Blankenau said. “It was considered more treacherous than parts of the Mississippi.” Even so, the Graysons made it across, reaching the small settlement of Civil Bend, Iowa.

When Nuckolls realized what had happened the next morning, all hell broke loose. He searched along the Missouri River, stationing lackeys at known crossing points.

By Dec. 1, Nuckolls had lost his patience. He guided a group of around 40 to 70 men to Civil Bend. 

It “became a veritable mob,” Blankenau writes. The men were armed with clubs and firearms, and witness accounts say many of them were drunk.

They ransacked the house of a local Black family, the Garners, dragging brothers Joseph, 20, and Henry, 19, into the nearby woods and whipping and choking them. Nuckolls put a rope around Henry’s neck but stopped short of killing him.

At the home of abolitionist Reuben Williams, Nuckolls drew a pistol as one of his brothers hit Williams with a cane so hard that he was partially deaf for the rest of his life.

The mob raided every home in Civil Bend — but their brutal, drunken search didn’t work. Blankenau says at one point, the mob searched the very house where the Grayson sisters were sequestered but still didn’t find them.

“I can just imagine they were terrified,” she said. “The consequences of them being caught, they knew that well.”

The warrantless searches continued the next day — then locals finally had enough. A local magistrate issued an arrest warrant for Stephen Nuckolls and 14 other members of his mob. Nuckolls was charged with assault, and news of the rampage made headlines across the country and even abroad.

Nuckolls had legal arguments of his own. In a 13-page suit filed in Otoe County, Nebraska, he accused 16 Iowans of violating the Fugitive Slave Act, a now-infamous law that required people even in free states to help return escaped slaves. Named as a defendant in his suit was Reuben Williams, the abolitionist whom Nuckolls’ mob had just brutalized.

It’s a little unclear where the Grayson sisters were at this point, Blankenau said. After all, supporters were intentionally keeping them hidden. 

She believes they may have slipped out of Civil Bend on Dec. 3. From there, she says they stopped in sympathetic towns like Lewis, Grinnell and Iowa City on their way to Chicago.

Back in Nebraska, Nuckolls was facing more bad luck. The Nebraska Territorial Legislature passed a law banning slavery in the territory, though it was ultimately vetoed by Governor Samuel W. Black.

The Nuckolls’ violent and controversial raids into Iowa likely played a role, Blankenau said.

“You want to boost that this is a nice, growing, vibrant place,” she said — “not a place that seems lawless, where you could be minding your own business and, all of sudden, these ruffians come in and take your feather bed and rip it up and then pour milk on it.”

In September 1859, Stephen Nuckolls and one of his brothers were found guilty of assault with intent to commit great bodily injury in their attack on Reuben Williams. 

They were fined $100, not much money even then. Williams also won a civil judgement ordering Nuckolls and his mob to pay $8,000, the equivalent of more than $300,000 today.

Collecting such a sum would be another matter — and the story of the Grayson sisters had not yet reached its climax.

It was 1860, the year before the Civil War, and slavery was top of many Americans’ minds. Illinois lawyer Abraham Lincoln had just been elected president on a platform of stopping the spread of slavery. As for Nuckolls, he was still determined to recover what he saw as his lost property. He learned that Eliza Grayson had been spotted in Chicago. In November 1860, he traveled there himself.

What happened after Nuckolls reached Chicago is a little unclear, the actual facts lost in a haze of commotion.

U.S. Commissioner Phillip Hoyne, who was presiding over the case in federal court, deputized a man named Jake Newsome to assist Nuckolls in finding the Graysons under the Fugitive Slave Act. As the story goes, they found Eliza Grayson in Chicago and were in the process of trying to arrest her when an angry crowd surrounded them.

A local abolitionist Chancellor L. Jenks started scuffling with Newsome. The crowd became agitated.

Although accounts vary widely at this point, Grayson was arrested by local authorities. Some say Jenks orchestrated the arrest so that she would be held by local anti-slavery authorities rather than being taken by Nuckolls. A group of abolitionists then helped her escape, with authorities doing little to stop it.

A grand jury indicted Jenks and others under the Fugitive Slave Act, though charges would soon be dropped as the Civil War began.

President James Buchanan, who was strongly pro-slavery, was is in the final months of his term. He apparently thought “Chancellor” was a title rather than Jenks’ first name. In an amusing detail, he telegraphed the local U.S. attorney, demanding that Jenks be removed from office.

What ultimately happened to the Grayson sisters is unknown, but it does seem that they made it to freedom. Census data from 1861 indicates Eliza Grayson probably settled in Windsor, Ontario, across the border from Detroit, when records show an “Eliza Grason” living in the city.

Not only did Nuckolls not get his slaves back, he also played some role in the collapse of the institution in Nebraska. 

Slavery became illegal in the territory in January 1861, just as the United States was beginning to tear apart. Nebraska fell onto the Union side. After the Battle of Appomattox, Union veterans poured into Nebraska, seeking land under the Homestead Act. The territory became a state in 1867.

Although Nuckolls lost his slaves, he never exactly faced accountability for leading a drunken mob on a rampage through Iowa. He moved around the West after the Civil War, continuing his political career as a representative of Wyoming Territory.

Reuben Williams sued Nuckolls in Otoe County District Court, claiming he never got all the money awarded to him. “Court records do not reflect that he ever got the entire amount,” Blankenau said. Nuckolls did hand over some money, which Williams used to build a barn that soon burned down. Although it was never proven, Civil Bend residents were sure Nuckolls had hired someone to take revenge.

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