Jesse and Mary Riddlesbarger

One Leading Businessman Lost It All in the Civil War

Jesse’s life is a “striking example of the mutations of fortune.”

By Diane Euston

  The war had not been fought yet. Before the Kansas City area was split in two, there was an event that would remain painted in the fond memories of those who fell on the wrong side of history.

  Above the current grade of downtown Kansas City, a neighborhood known as Pearl Hill (what would be considered 1st Street and bordered 2nd St. to the south, Grand St. to the east and Main St. to the west) was the headquarters of Southern sympathy. 

  They gathered as if it was a holiday. Seats for the grand showcase were “reserved” by the city’s finest pioneer families. Women amassed on the sweeping front porches to ensure their view of the day’s activities. From the Riddlesbarger mansion, women in their finest garb filed in and festered over the Southern cause on a large porch facing the Missouri River.

  In order to make their viewpoint seen and not heard, Jesse Riddlesbarger and his Southern friend, Charles Kearns ensured that the Confederate flag hung high from this hill. It was, in fact, the first Confederate flag raised in Kansas City.

  The women cheered and waved handkerchiefs. Beside the flagpole was a well-positioned working cannon aimed at the invisible New England states.

  As the well-dressed women took their seats on the porches of these Southern-built mansions in now-downtown Kansas City, hoisted over 60 feet above current-day Kansas City, the men gathered around the cannon to set it straight. An enormous crowd, “wild with enthusiasm” gathered and the cheers could be heard as each flint was lit and cannon flew freely over into the Mighty Missouri River.  

   These Kansas City pioneers certainly had Southern tendencies. In this neighborhood situated well above the grade of the blossoming city below it, this was felt from every corner of its being and would partially lead to its death within the city’s landscape.

  Leading the charge of this ardent support for the south was Jesse Riddlesbarger (1800-1883), a man with few apologies who would fall quickly from one of the richest men in Kansas City to a destitute man with little left to show from his prior life – all tied to his choices to side with the South.

Kansas City in 1850. Businesses on the levee can be seen as well as some of the homes which stood high on Pearl Street Hill. Courtesy Missouri Valley Special Collections, KCPL.

Jesse’s Rise in Business Ventures 

  Jesse Riddlesbarger was born in Maryland in 1800 to parents Samuel and Sarah. When a young child, the family relocated to Botetourt County, Va. In 1827, Jesse married Mary Sproul in Virginia, and by 1830, the couple relocated to Fayette, Mo. 

  Fayette was certainly a place rooted in Southern politics and hospitality. Most of its early settlers came from the Upper South, and they brought with them the institution of slavery and continued production of Southern staples including hemp, tobacco and cotton. Because of their traditions, this area became known as Little Dixie, and Fayette, the county seat of Howard County, was directly in the middle of this geographic area. 

  In 1830 when the Riddlesbargers had made their home in Fayette, over 30 percent of the county’s population was enslaved. By 1840, Jesse had three enslaved people. Jesse was one of the first gunsmiths in the county and likely made his early living in Missouri in this industry.

  In about 1843, Jesse saw an opportunity to make some money in the mercantile business. With partner J.D. Perry, they opened a firm in Fayette called J.D. Perry & Co. Within three years, the enterprising man had established himself on top of the mercantile trade; the business was rebranded J. Riddlesbarger & Co. 

  In 1847, Jesse took over the entire business and continued running it until 1851. The business certainly afforded Jesse and his family a nice living; by 1850, they employed three domestic servants and held five enslaved women. Seven children of Jesse and Mary’s survived to adulthood.

  Jesse was wealthy, but he was hungry for more. When the Mechanic’s Bank in St. Louis was looking for an investor to take the helm at a new branch in blossoming Kansas City. The opportunity came at a perfect time. Westport Landing (as the levee on the Missouri River was called) had quickly become a hub of Santa Fe travel. This, in addition to the possible land expansion west of the Missouri border made the moneymaking possibilities endless. 

  When Jesse arrived in Kansas City, he built Mechanic’s Bank against a bluff at the northwest corner of 2nd and Main St. From the basement of the building, the Santa Fe stages organized their ventures to the west.

  In 1852, Jesse’s wife, Mary passed away shortly after giving birth leaving him a widow at 52 years old. At his house at 3rd and Delaware, Jesse lived with his adult children and, in addition to being president of Mechanic’s Bank, began buying and selling real estate.

Kansas City in 1855. Houses on Pearl Hill can be seen as well as businesses on the levee. The hills were removed when street grading began in the late 1850s. Courtesy Missouri Valley Special Collections, KCPL.

A New Wife and Life on Pearl Hill

  In 1853, 53-year-old Jesse Riddlesbarger was the talk of the town when he remarried to 16-year-old Susan Lavinia Norton. Her father, Dr. Joshua Norton, kept a drug store on the levee. Susan was extremely beautiful. “Her complexion was dazzling, her cheeks crimson, her hair jet black,” the Kansas City Star later wrote.

  In that same year, Jesse’s oldest daughter, Harriett married William G. Barkley, nephew of William Gilliss and Mary Ann Troost’s half-brother. This marriage helped to further solidify the Riddlesbargers as one of Kansas City’s most prominent families. In about 1857, Jesse began to build a house for his young wife on 2nd Street and Walnut in the fashionable Pearl Hill neighborhood. “A commanding site was chosen for the new home” at the crest of the bluff with unimposing views of steamboats coming up and down the river.


  Jesse spared no expense for this new mansion. He imported brick from St. Louis for the exterior. Inside, an elaborately carved walnut staircase was framed by crystal chandeliers with coal oil lamps. Large marble mantles imported from Italy graced each room, and the drawing room included carved rosewood furniture. The velvet carpets, imported from Brussels were matched with the first French wallpaper ever brought to Kansas City. Engravings of Robert E. Lee and Stonewall Jackson covered a prominent wall inside the home.

Jesse Riddlesbarger’s impressive mansion, built about 1857, at 2nd and Walnut. The house was known as the most expensive house built in the city. Carving out the bluffs sealed the fate of this home and others in the Pearl Hill neighborhood. Image courtesy John Dawson

  In this mansion, the Kansas City Star wrote in 1929, “the young bride reigned like a queen. . .  [Jesse] gave her everything she desired – beautiful dresses, a velvet mantle, a bonnet with the finest of French roses that wreathed her face as she wore it, a set of corals that set off her black hair.” 

  Hulda, an enslaved cook in the Riddlesbarger home, was famous for her home-cured hams, gingerbread and fried chicken. 

   William Barkley and his wife, Harriett moved into the original home occupied by Jesse, and in May 1857, the two-story brick house at 3rd and Delaware was the site of the organization of the first Presbyterian church.

Jesse Riddlesbarger’s second wife, Susan. The image was printed in the Kansas City Star.

Mixing Business with Southern Tendencies

  In 1855, Jesse Riddlesbarger teamed up with some of Kansas City’s finest businessmen – William Gilliss, Benoist Troost, Milton Payne, William S. Gregory, Milt McGee and others – to finance Kansas City’s first newspaper, The Kansas City Enterprise. The men had one thing in common: they were all slaveholders.

  The original editor hired for the newspaper wrote several editorials about abolishing slavery that concerned the men. In July 1855, Robert Van Horn was hired as the new editor, and Jesse was in charge of the paper’s finances.

  In December 1855, Jesse purchased Lot 5 on the levee and began building a warehouse and commission business. Nearby businesses included the JP Shannon Dry Goods Store, Dr. Benoist Troost’s medical and real estate office, Jarboe’s mercantile store and William H. Chick’s warehouse.

  The goal of this new business venture was to store goods for people and businesses relocating to the area while also outfitting caravans departing on the Santa Fe Trail. He first went into business with Edward McCarty, his former cashier at Mechanic’s Bank and head of the Law and Order Party. McCarty published broadsides in the Enterprise openly calling for Kansas Territory to accept slavery. 

  Within a year, Jesse’s son-in-law, proslavery businessman William Barkley, went into business with McCarty as partner at J. Riddlesbarger & Co. on the levee. They advertised, “Particular attention paid to receiving and forwarding all goods consigned to them.” 

An 1850s advertisement appeared in the Kansas City Enterprise newspaper.

  Interestingly, J. Riddlesbarger & Co. had a contract with the New England Emigrant Aid Company. It was established in response to the Kansas-Nebraska Act in 1854. The company guaranteed low-cost transportation to Kansas Territory and helped with temporary housing once they reached there. The goal was to encourage anti-slavery men to move and ensure these men would vote in territory elections.

  Abolitionists were flooding the riverfront and moving into Kansas Territory to ensure that with popular sovereignty, those elected into the newly-established territorial legislature would ensure Kansas was a free state. 

  As these abolitionists moved their goods to Kansas City, they chose Jesse Riddlesbarger as the man to receive their property. This may be surprising, but most of Kansas City’s prominent businessmen were proslavery and pro-money making. Men like Jesse were willing to overlook anything in order to make a fortune.

  The clashes over slavery were at a boiling point in the area as the nation inched closer to civil war. Acts of violence, coined “the Border Wars,” plagued the community surrounding the booming town. Kansas City’s businessmen did their best to put a lid on the violence within the town in order to continue business as usual.

Banishment Under Special Orders

  Although the area had been under attack for years due to proslavery and antislavery clashes, the arrival of the Civil War in April 1861 brought federal troops for the first time to Kansas City. 

  Most businessmen in the city chose to placate their Southern views when they arrived in order to continue their businesses unmolested. Late historian John Dawson wrote, “Riddlesbarger was unapologetic, unrepentant, and spoke his mind without reservation.”

  In December 1861, Provost Marshal Plumb, assigned to Kansas City, compiled a list of “Rebel and Rebel Sympathizers who are prominent citizens of Jackson County.” Included in this list was Jesse Riddlesbarger. 

  The Kansas City Star later wrote, “[Jesse] was hot-headed, autocratic, and he believed implicitly in the merit of the Southern cause. He spoke his mind everywhere. He felt such hatred and ire for the northern troops stationed in Kansas City that he seized every opportunity to criticize and even to taunt them.” 

  This behavior backfired. In March 1862, a fire destroyed two large businesses on the levee. One was none other than Jesse Riddlesbarger’s “fire-proof building,” and it is likely that Union troops were behind the arson. His house was raided by Union troops with the intent to burn it. Friends with proven loyalty convinced the soldiers to leave. 

  This event forced Jesse to reconsider his residency – at least on Pearl Hill. He transferred ownership of his stately home to Patrick Shannon, a friend. His likely motivation was to protect the house from further destruction.

  A series of events in the area in 1863 resulted in some of the harshest orders against civilians in U.S. history. Brigadier Gen. Thomas Ewing, in charge of the District on the Border, was crippled by guerrilla violence. Bushwhackers such as William Quantrill were able to taunt and kill Union soldiars; they were able to survive on the run due to the support of rebel families. Thus, Gen. Ewing opted to arrest men, women and children suspected of supporting them.

  A prison collapse in Kansas City on August 13 killed four people, including the sisters and cousins of infamous guerrillas that had been arrested. In retaliation, Quantrill and hundreds of guerrillas rode into Lawrence, Kan. and killed 160 to 190 men and boys.

  Gen. Ewing was under intense pressure to respond swiftly and unapologetically; it was time to squash the guerrillas once and for all. On August 25, Gen. Ewing issued General Order No. 11, forcing all citizens living in Jackson, Cass, Bates and part of Vernon Counties who could not prove their loyalty to vacate within 14 days. The only people exempted were those living in Kansas City, Westport and Independence where Union forces were present.

This letter under Special Orders No. 64 banished Jesse Riddlesbarger and his family from the city in 1863. He would never return.

  There was an exception, of course. A soldier arrived at Jesse Riddlesbarger’s home on August 29, 1862 with a piece of folded paper in his hand. Jesse’s young wife, only 25 years old, held her two girls, six and one, close to her as she answered the door. 

  Delivered to her was a copy of Special Order No. 64, signed by Gen. Ewing.  It read:

  Jesse Riddlesbarger and family, residents of Kansas City, Mo. Are ordered to remove from this District within ten days from the date hereof. They will not go to the counties of Platte, Clay, Ray or Carroll, Missouri to reside, nor return to this District during the rebellion without previous express permission from competent military.

  To add insult to injury, Jesse’s property, including 37 valuable lots on Main St., were confiscated. In all, 64 citizens from Independence Kansas City were banished. Included was Kansas City founders William Gilliss and John C. McCoy and William Barkley, Jesse’s son-in-law.

William and Harriett (Riddlesbarger) Barkley’s home at 3rd and Delaware in 1868. Like all houses on Pearl Hill, carving out the bluffs made these homes impossible to reach over time. This home was originally the Jesse Riddlesbarger home before he built his mansion nearby.

Picking Up the Pieces

  Jesse took his family along with all of their movable possessions by steamboat to St. Louis. There, he opened a small grocery store and rented a space above it to live in; the business quickly failed. 

  His next thought was to try his luck in Quincy, Ill. The family boarded a steamboat with all of their valuable belongings. The boat hit the bottom and quickly began to sink. The family survived, but the beautiful furniture that once graced their Pearl Hill home was damaged by water.

  Jesse opted to turn around and go back to St. Louis where they tried desperately to sell the furniture at auction; it fetched low prices and left them destitute.

  The family rented three small rooms in St. Louis while Jesse worked for $40 a month at city hall. The couple’s last child was born in 1869 when Jesse was months from his 70th birthday.

  After the Civil War, the condition of the family didn’t improve. The once-wealthy Riddlesbargers didn’t have money for their basic needs, and for a time, Jesse even worked as a night watchman.

  In the early 1880s, Jesse moved his family back to Fayette, Mo., and in 1883, he died at the poorhouse. One year later, his second wife, Susan died in St. Louis at the age of 46.

Repent or Regret

  It’s hard for us to understand in the 21st century what could have motivated a man like Jesse Riddlesbarger to risk everything for the institution of slavery. 

  Other Kansas City leaders who stood for the same backwards principles were able to bounce back and returned to the city they helped build. William Gilliss, John McCoy, William S. Gregory and others who once were slaveholders kept, for the most part, their mouths shut as the shifting climate turned toward the Union.

  Jesse Riddlesbarger’s pride – his incompetence in recognizing what could be taken from him– caused him to believe he was invincible. His wealth, to him, was impenetrable. Once his footing was taken out from under him, he was unable in his advanced age to regain any semblance of his wealth, prestige and power. 

  His once-impressive house on Pearl Hill was demolished around 1900 as the city carved away the bluffs to make way for the future. It, too, represents how even the finest of things can be destroyed, and Jesse’s life is a “striking example of the mutations of fortune.”

Diane writes a blog about the history of the area. To read more of the stories, go to 


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