On the road to freedom: Three stories of Jackson County’s enslaved (2025)

By Diane Euston

In the 1830s, an influx of families, predominantly from Virginia, Kentucky and Tennessee, moved to Jackson County on the western edge of the United States. Many of them brought with them enslaved individuals, some of whom had served these white families for generations.

The institution of slavery was paramount to the success of this planter class, but the way in which the institution was structured was quite different from the large, sprawling plantations of the South.

In general, this is not the way that slavery looked in western Missouri. To be clear, this doesn’t mean it was any less harsh or acceptable. These settlers who chose Jackson County as their home brought with them a few enslaved who didn’t choose to move. This small slaveholding structure was the backbone of many of these early settlers’ lives.

Piecing together the stories of people in bondage is very difficult work due to lack of primary sources and very few stories published about their lives pre-emancipation. But there are some stories about the formerly enslaved who once worked in Jackson County that do survive.

Let’s take a step back in time and look at the incredible stories of three formerly enslaved men who, with their families, overcame the chains of bondage and built lives for themselves after emancipation.

From Independence, Mo. to Independence in Kansas: Sam Shepard

When Sam Shepard passed away in 1909, the newspapers had already speculated the man’s age years prior. It was estimated he was well over 100 years old.

Samuel Bailey Shepard’s name over time was mentioned in the history books because of his role in a crucial point in Jackson County’s history, and unlike so many stories of the enslaved, we are able to identify him before and after emancipation.

Sam was born in Lee County, Va. around 1810 and was enslaved by James Pendleton Shepherd (1767-1853). His slaveholder married Rachel Gault in 1797.

By 1820, Mr. Shepherd held three people in bondage in Lee County; a female between 14 and 25 and two boys under 14 years old. Because children followed the condition of the mother, this is likely Sam’s mother and his brother, Peter.

About 1824, Mr. Shepherd opted to move to Jackson County, Mo. Some of his adult sons followed. Two years later, the county was established. The Shepherds settled on land just south of current-day Independence.

Early historian William Z. Hickman (1845-1921) documented the founding of the county and the pioneers who settled in the area in his “History of Jackson County, Missouri.” He also had a front row seat to some of Sam’s stories, because Hickman’s father, Edwin Z. Hickman (1819-1887) later purchased Sam.

“It was as a child, sitting out in the negro quarters on long winter nights, that I listened to Sam tell of his early life, when he first came to this country,” Hickman wrote.

Sam told Hickman that he was taught to use a firearm for protection from Native Americans and for the purpose of shooting his food. In the early days of the county, everyone relied upon wild game as food.

When the government was organized in the town of Independence, a courthouse needed to be built. It was a simpler time where settlers crossed the plains on the Santa Fe Trail with hopes of a better life. When the newly-formed government voted to establish a courthouse in Independence in 1827, the contract for $150 went to James P. Shepherd. He also served as an early county clerk. Mr. Shepherd supplied enslaved Sam and his brother, Peter to build the courthouse at its original address of 117 E. Lexington Ave.

Sam, an experienced carpenter, hewed the logs for the very first courthouse in the county. The building was used for this purpose for about nine years until a brick courthouse was built. The building was then used as a goods and merchandise store.

In the winter months when work was limited, Mr. Shepherd hired out Sam and Peter to salt makers in Saline County where they cut cord-wood. “They were both experts with the axe,” Hickman wrote.

When James Shepherd passed away in 1853, Sam was purchased by Edwin A. Hickman. Since it was well-documented that Sam was a great carpenter, it makes sense that Hickman had use for his labor. He had established a sawmill outside of Independence in 1847. In 1854, he established a steam-powered gristmill and sawmill in the southern portion of the county.

Today, this area is known as Hickman Mills.

While enslaved, Sam married Julia Newson (b. cir. 1812). The couple reportedly had 10 children.

After the Civil War broke out, Sam fled with his family to Lawrence, Kan. in 1862, well-known at the time for its safety on the Underground Railroad. There, Sam continued to work hard to support his family.

When he was too old for work, he was still a fixture of the Lawrence community, well-known for his politeness. “Every morning, he would come up town and he delighted to ‘loaf’ around stores and places listening to people talk,” the Lawrence newspaper wrote.

In 1908, the Independence Commercial Club met to discuss saving the old courthouse, built with Sam Shepard’s hands in 1827. William Z. Hickman read a letter from Sam Shepard. The Kansas City Star reported, “[Sam] desired Mr. Hickman to help find other members of the Shepard family, if there are any, also to find out how old he was.”

The fact that he didn’t know where some of his family was suggests that at some point, the family was sold off and lost forever. The members of the committee discussed how old they thought he was, and Hickman felt he was “well over 100.” An 83-year-old police judge in Independence commented, “I knew Shepard 65 years ago, and I thought he was a mighty old negro then.”

The mystery of Sam’s age would never truly be revealed. Sam closed his eyes for a final time at his daughter’s home on Pennsylvania Street in Lawrence on February 8, 1909. He is buried at Oak Hill Cemetery where a marker claims his date of birth as 1784- a clear exaggeration.

Regardless, Sam saw so much in his lifetime, and a small piece of his contribution to the county can still be seen today. Miraculously, the original courthouse has been preserved after being moved to 107 W. Kansas St. Harry S. Truman even used the building in the 1930s when the courthouse was being remodeled.

Sam’s hand-hewn logs survive today, and in its lifetime as a courthouse, all of the early business and important transactions occurred within it.

The Respected Blacksmith: Troy Strode

Troy Strode was born about 1823 in Gallatin, Tenn. in bondage. His slaveholder, Charles Edward Strode (1814-1882) was born in Kentucky and moved with his parents to Sumner County, Tenn.

When Charles’ father, James died in 1829, his probate indicated there were 12 enslaved. Charles inherited a “boy named Troy” when he was just 15 years old.

It’s clear from the division of property that Troy was separated from his family. In about 1834, Charles Strode opted to start a new life in Jackson County, Mo. Following him were his mother, Margaret, two brothers and one sister.

An article in 1898 claimed, “Charlie Strode risked the penalty of fine and imprisonment, taught his slave [Troy] to read and write.” Other documentation claims that as a child, Troy was often sick and that gave his slaveholder time to teach him to read.

His two brothers settled in southern Jackson County just east of current-day Grandview, Mo. Charles followed with land bordering current-day 150 Highway and Raytown Road.

In 1838, Charles married Sarah Weston. While his brothers stayed south, Charles lived various places until about 1848 where he opted to move to Independence where he worked as a merchant.

Somewhere along the way, enslaved Troy learned the trade of blacksmithing. Even though he was separated from his brother, Jordan (who was enslaved by Charles’ brother, William), they both were trained blacksmiths.

While living in Independence, Troy met his future wife, Julia, who was enslaved by a notorious slaveholder of the area.

Jabez Smith, born in 1787 in Pittsylvania County, Va., was quite the businessman. When he opted to move to Jackson County, Mo. in 1844, he brought with him about 200 enslaved. One of these people in bondage was Julia, born about 1833.

Jabez lost his first wife the same year as his move, and he certainly didn’t go unnoticed when he rolled into Independence, Mo. with hundreds of the enslaved.

The slave population for all of Jackson County was 1,361 just four years prior to Smith’s arrival. Just shy of 30 enslavers held 10 to 20 enslaved in 1840.

And here was Jabez Smith with approximately 200 enslaved. Needless to state, he was the largest slaveholder in the state of Missouri.

Jabez settled on thousands of acres of land in the Independence area and dabbled in the freighting business. He held landholdings in various states and eventually turned toward speculation as his career.

In 1851, 64-year-old Jabez Smith married the beautiful 18-year-old Ann Eliza Keane. They settled into his 15-room brick home at current-day 24 Highway and Noland Road- the site today of William Chrisman High School.

Northeast of his home, slave cabins covered the hills. Due to the size of this slave population, the enslaved were separated from one another on 15 different farms named, for the most part, after the head of the enslaved family. This included Aunt Dinah’s Farm, Brunswick’s Farm and Henry Carter’s Farm.

Where Julia fit into these households is unknown; however, by 1850, the 17-year-old girl met and married Troy Strode, the enslaved blacksmith in Independence. “Abroad” marriages with the enslaved where couples lived on separate farms was not uncommon in Jackson County due to the usual small-slaveholding structure of the household. Troy had to look abroad for a marriage; in 1850, he was one of three enslaved held by Charles Strode.

When Jabez Smith died in 1855, Julia, along with 310 other enslaved individuals, were listed in his probate by family group. There, Julia is listed alone with her three children: Eliza (b. 1850), Anna (b. 1852) and William (b. 1854). Her appraised value was $750.

The 311 enslaved were divided between Jabez’s second wife, Anna, and his three surviving children. The probate noted there was effort to “keep families of slaves together.” The probate indicates that in December 1855, the estate was valued at a whopping $161,550.

Julia and her three children were willed to Jabez’s widow, Ann. In 1856, Ann married James Polk. In 1860, the 40 enslaved remained in Independence.

The want of keeping the families of the enslaved together didn’t seem to last. At the onset of the Civil War, Ann’s husband enlisted in the Confederacy and the enslaved were moved “down South” to Arkansas.

Prior to the Civil War, the couple had four children. The two girls, Eliza and Anna, “were sold into slavery and were lost forever by their parents.”

How Julia didn’t end up in Arkansas is unknown. What is known is that in October 1861, the notorious Col. Charles Jennison of the 7th Kansas Calvary “went into Missouri for the purpose of liberating slaves.”

Troy took this opportunity, the newspaper later reported, and took a team of oxen and covered wagon to Lawrence with his wife and two children.

Troy started his own blacksmith shop on the 900 block of New Hampshire Street. During the Lawrence Massacre on August 21, 1863, Troy’s experience was one of the remarkable escapes. Historian Richard Corley recalled that Troy “had a little patch of tomato vines not more than 10 feet square. He took his money and buried himself among the vines. The raiders came and burned his shop not more than 10 feet from him, but did not discover him.”

By 1865, other Strode formerly enslaved, including Troy’s brother Jordan, joined him in Lawrence and worked at his blacksmith shop on Massachusetts Street. He later moved to a lot on Henry Street and purchased additional real estate; he was “known to every citizen in Lawrence.”

Troy was also a leader within the growing Black community of Lawrence. In September 1862, he along with 15 others organized the Second Congregational Church, then known as the Freedman’s Church. He was one of the few Black men who could read, so “he was a great service to the church, being a good reader and a good singer.”

As he advanced in age, continuing his blacksmith business was impossible. In 1886, he retired to his home on New Jersey Street and passed away in 1898. His wife predeceased him in 1892.

Three of their 12 children survived him.

A Freedman in Pro-Slavery Westport: Winston Dillard

At the center of proslavery activities along the border was Westport, Mo. where most settlers held staunch to their beliefs. In 1860, there were only a handful of freedmen living in Jackson County, and out of these, only five lived in the town of Westport.

One of them was Winston Dillard.

Winston sat down with a reporter from the Kansas City Star in 1898 where he told “of things he usually kept buried deep in his heart.”

To be fair, the article had some factual issues, but the story about the “kind” and “gentle” light-skinned man opened up a lens into a time rarely captured in print.

Born about 1820 in Henry County, Va., Winston was the property of William Hill and his wife, Elizabeth. When William passed away in about 1827, his will indicated that he wanted his wife to inherit his eleven slaves. This included Winston and his mother, Viney.

William and Elizabeth Hill’s daughter Martha (1785-1855) married George Dillard in 1803.After Martha’s mother died, Winston and his mother, Vina (“Viney”) passed to her.

In about 1844, Martha Dillard moved with a group of her extended family to Jackson County. By 1850, she had settled with her son, James on a parcel of land at current-day 39th and Washington where Our Lady of Good Counsel stands today in Westport.

There, Viney cooked meals for the Dillards. Nelly McCoy Harris (1840-1926), daughter of Westport founder John C. McCoy, fondly remembered Viney and how she was able to work to save money while enslaved. “[Viney] assisted in laundry work or housecleaning in the neighborhood and laundered in her cabin the linen of many bachelors of the town,” she recalled. “But Mrs. Dillard’s table was not neglected. There bounteous hot meals, as was then the custom, were provided by the skillful, sturdy negress every day in the year.”

Winston also worked to save his money away. He took the little portions of money he earned from doing extra jobs. “When my missus died, I had more than $300 hid away under the floor in my cabin,” Winston claimed.

When Martha Dillard died in 1855, the probate administrator valued the property, including Winston, 36, at $1000, “Vina,” 60, at $400 and two other enslaved. It was decided by the heirs to sell the enslaved “at the courthouse door” April 7, 1856.

Winston approached his old mistress’s son, James, just before the auction and told him that he wanted to buy his freedom. “[James Dillard] told me to see if I could get someone to go on my bond for the amount I should have to pay for myself,” Winston recalled.

Westport merchant Alexander Street and Jesse L. Porter (1820-1868) agreed to help him. This was an unlikely duo to come to his rescue. Street enslaved two people in 1860, and Jesse’s father was one of the larger slaveholders in the area; in 1860, Jesse held 20 enslaved in bondage at his home off current-day 27th and Troost Avenue.

Regardless, the bidding closed at $1,000 with Jesse Porter named as Winston’s purchaser. Winston didn’t have all the money to cover the bond, but James Dillard and his sister, Jeanette, two of his former mistresses’ children, gave him $100 each to cover it.

Winston’s mother was a different story that he didn’t talk about in the newspaper. Viney was purchased by a man living in Kansas Territory named Wesley Garrett (1823-1894) for $413. A clue to his motive is revealed deeper in the documents.

Winston earned a living by trading commodities to Native Americans, and in 1858, he was able to throw down $100 on a lot at the northwest corner of Pennsylvania Avenue in Westport. There, he built a log cabin.

A year later, another deed surfaced in the records. It shows that Winston Dillard “borrowed” $225 from none other than Wesley Garrett. He used his property as surety.

These unique records indicate that it’s quite likely that Winston and his mother worked together to pay off the $418 note for the sale, and Wesley Garrett never intended to enslave Viney when he purchased her. Viney Dillard, about 50 years old, was finally free. In 1860, she was living with her son in their little log cabin in Westport- one of only five free people of color in the town. She died sometime after 1870 in Westport.

What makes this story especially unique is the fact that Winston and his mother were free before the Civil War, and instead of leaving the town that had been their home for less than two decades for friendlier conditions like Lawrence, they stayed.

Winston married at least twice, and interestingly, one wife was a French-born white woman named Mary. He was the father to at least five children with several dying young. Some of his children stayed in Westport, settling in the Steptoe neighborhood. Winston passed away in 1910 inside his little house he worked so hard for.

As he sat down for an interview with the Kansas City Star on his little porch at 3919 Penn in Westport in 1898, Winston was quite reflective of all he had seen and endured in his lifetime. “This house here belongs to me,” Winston said. “And from whose front windows I have seen Westport grow from a wild, frontier settlement to the suburb of Greater Kansas City.”

The Complexity of our Collective History

These three stories, all unique, stem from the drive of Western Expansion and its connection to slavery in Western Missouri. When pioneers from the South chose this area as their home, many of them, including those revered for their contributions to our area’s history, brought with them men, women and children in bondage.

These people cultivated the land, built structures, fixed wagons and equipment, cooked, sewed and raised the children of many of their slaveholders. Due to the elusiveness of records, oftentimes these people are no more than an age, color and sex on a slave schedule or a tax sale. Their identities, for the most part, remain unknown.

Professor and historian Henry Louis Gates said, “The thing about Black history is that the truth is so much more complex than anything you could make up.”

The stories of these three men profiled here on their road to freedom shows the complexity of their lives and the contributions they made while ensuring they carved out a fulfilling life after they broke the bondage of enslavement.

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