With a crime rate of 45 per one thousand residents, Harlan has one of the highest crime rates in America compared to all communities of all sizes – from the smallest towns to the very largest cities. One’s chance of becoming a victim of either violent or property crime here is one in 22.
It was November 2004 while on a trip to Harlan County with my father, I first heard the remarkable true story of Rebel Rock. While discussing family history with my grandfather’s cousin, Kellis Metcalfe (1939–2015), I learned how three of my great x 5 uncles were responsible for one of the most enduring legends of Eastern Kentucky.
The captivating feeling of hearing for the first time a family secret that obviously implied my ancestors’ Unionist loyalties during the American Civil War and named the legendary “Rebel” made me determined to someday have the story published.
Eight years later in August 2012 while visiting the Metcalf cemetery with my brother I stumbled across a tombstone inscribed with the initials of the Ku Klux Klan. This is the story of both hidden secrets and the history buried with them.
Hotbed of Home Guards and Bushwhackers
Harlan County, located in the Cumberland Mountains of southeastern Kentucky, during the American Civil War was fiercely Unionist. With only 19 slave-owners and located inside an Union state, its not surprising Harlan had few wartime Southerners. Of the local men and women who eventually chose a side in the war, the overwhelmingly majority of them sided with the North to preserve the Union of the United States. Their hatred of the Confederacy and the war itself had been hardened by the South’s foraging of food which left the people of Eastern Kentucky and Appalachia starving.
In order to protect them and their families, the Unionmen of Harlan formed local units of the Home Guard. Little more than an armed neighborhood watch that sometimes had official recognition as a state militia, the Home Guard usually was the only defense for these mountaineers. One area of Harlan particularly known for Home Guard activity was Poor Fork. Enclosed on both sides by Black and Pine Mountains, the narrow river valley gave an advantage to locals to bushwhack foraging invaders while safely hidden in the thickly forested mountainsides.
During one of these foraging raids, a Rebel was chased up a spur of Pine Mountain that was used as a hiding place and lookout point for soldiers passing through. With no way out except a sudden 100 foot drop off the cliff, it is said the Rebel either jumped to a nearby tree for safety or was thrown to his death by his Unionist pursuers. For this reason the distinct and recognizable cliff received the name, “Rebel Rock.” Situated between the towns of Cumberland and Harlan, Rebel Rock overlooks the Old Laden Trail which now roughly follows State Highway 2010 that cuts through Kentenia State Forest and intersects with the Little Shepherd Trail.
Living in the shadow of Rebel Rock’s spur, the people of Harlan County had a constant reminder to keep the Civil War story of Rebel Rock alive. However despite its notoriety, the participants in the chase and skirmish remained anonymous in published folklore. Now 150 years* later the true story of Rebel Rock can finally be told.
Name of the Rebel Revealed
The identity of the Rebel was thought to have been forgotten, but according to a family story told to Kellis Metcalfe of Harlan County, Rebel Rock is named after a “Reb Spy” called “Captain Tom Crupper”.
As records show, there was a Thomas M Crupper who served in the Confederate Army. He stood at 5 foot 11” at a time when the average American man was four inches shorter. His eyes matched his dark complexion and whiskers; and in the summer of 1861, he was 22 years old when he left his home to enlist as a private in Company F of Brazelton’s Third Tennessee Cavalry Battalion.
Brazelton’s East Tennessee cavalry outfit took part in a number of foraging and scouting raids into Eastern Kentucky through the fall and winter. Towards the end of the year the Third Tennessee Cavalry was stationed at the important mountain pass of Cumberland Gap — then located at the southwestern corner of Harlan County. It was probably during this time that the then 22 year old Tom Crupper first visited Poor Fork and met his future wife, Ruth Creech.
On March 15, 1862 Tom Crupper and another private of Company F, William Ivy, were captured by Union pickets just north of Cumberland Gap in Knox County. The two had deserted after being sentenced to death by Confederate authorities for aiding in the alcohol-fueled shooting of Tazewell, Tennessee’s provost marshal, Lt. Alexander H. Vaughan on the night of December 27, 1861.
Crupper and Ivy had tried to switch sides after the fact by first turning in the “kid” responsible for firing the fatal shot and then assisting in the arrests of three or four other “perfect desperadoes” who had also participated. However this did not save them from also facing court martial.
Despite being Confederate deserters on the run from a firing squad, Crupper and Ivy were not paroled and instead were sent to imprisonment at Camp Chase in Ohio. They remained at Camp Chase until August 25th when 1,200 Confederate were put on a steamer heading to Vicksburg, Mississippi for exchange. Crupper took the oath of allegiance to the Union and had his name removed from the list of prisoners. Ivy instead chose to be sent to Vicksburg. As to why Ivy did, since that would mean having to return to face an execution, remains a mystery as does his fate.
Now 24 years old, the released Crupper went back home to Bracken County along the Ohio River. However he was back in Union custody three days later when he was caught violating his parole. Somewhere and somehow on the way back to Louisville, Crupper escaped from his two armed escorts and eluded them for a few days before being captured for the third time.
After a brief second stay at Camp Chase, Crupper was sent to Johnson’s Island along the coast of Lake Erie at the end of September. On April 6, 1863 Tom Crupper is listed as being paroled again and sent to Fort Monroe on the eastern coast of Virginia for exchange. As with common practice during the war, he probably just had his name on a list of released prisoners because by then, he was already back in Harlan County…
A Rebel in Poor Fork
Among the families of Poor Fork was the Thomas Creech family. The Creeches had settled what became Harlan County in the 1810s when Thomas Creech’s father led them across the Cumberland Mountains from Virginia. By the Civil War, old Thomas Creech had six sons and five daughters of his own with his wife, Celia Harrison.
His neighbors, the Metcalfes, led by John Adrian Metcalfe Sr. and Barbara Hensley, had moved from North Carolina in the 1840s. Their house sat the base of Rebel Rock where Old Highway 119 and Laden Trail intersects today. By 1855, Adrian and Barbara were dead — leaving behind three sons and five daughters ranging from 14 to 25 years old.
John Adrian Metcalfe Sr.’s three sons, Adrian, Ambrose, and James, threw their lot in with the Union when war came to the mountains. All three Metcalfe brothers were in the Harlan County Battalion of the State Guards that officially served from October 1862 until February 1863 when state funds ran out. Daniel Boone Creech and two other sons of Thomas Creech were also in the same Home Guard outfit.
The bonds between the two families were further strengthened when in 1857 two of Thomas Creech’s children married two of the Metcalf siblings: Daniel B. Creech married Nancy Metcalfe while Amy Creech married James H. Metcalfe. Then on March 30, 1863 the youngest of Thomas Creech’s daughters, 21 year old Ruth Creech, married Rebel outsider, Thomas M Crupper.
Not only were Crupper’s new in-laws and neighbors Unionist members of the Home Guard but so too was the Justice of the Peace, Jonathan Lewis, who presided over the wedding in Poor Fork that day. Just four days before the wedding, a Confederate regiment entered the county and destroyed the Home Guard’s camp in Poor Fork. Not too far behind these Confederate invaders were their commander, General Humphrey Marshall, and the rest of his small army from Virginia who occupied the county through May.
The coincidental timing of the arrival of the Confederate Army in Harlan might not only explain Crupper’s appearance but also the two witnesses listed at his wedding: Leander Branson and James Polling. The former appears to have been Leonard Branson of Perry County who served as a Confederate private in Caudill’s 10th Kentucky Cavalry. He was killed in a skirmish five months later with his brother in neighboring Letcher County. If this is the same Branson then this indicates a continued association between Crupper and Confederate soldiers despite his death sentence and desertion.
After the Confederates left “the hotbed of Home Guards & bushwhackers”, Union recruitment picked up in Harlan County. By November 1st, more than 50% of the eligible men of the county had volunteered to enlist in the Union Army. Those that didn’t volunteer faced the draft. Among the men of Harlan listed to be drafted in the summer of 1863 was the 24 year old Thomas M Crupper.
Crupper enrolled on July 23rd and joined a number of Harlan men in their journey to Camp Nelson to become an Union soldier. Assigned as a private to Company E, 49th Kentucky Mounted Infantry on September 19th, Crupper is immediately listed as being “absent in military prison at Camp Nelson” through November.
In December he returned to his regiment now stationed in Somerset for picket and guard duty. While at nearby Camp Burnside in early February 1864, Tom Crupper deserted. He headed back to the mountains of Harlan where nine months later on November 20th, his wife gave birth to Sarah Melissa Crupper.
Where the Paper Trail Ends
According to the story told to Kellis Metcalfe by a Metcalfe cousin, Crupper had been “courting Nancy Metcalfe and broke her marriage up”. The “Reb Spy” had been camping on top of Rebel Rock to be near Nancy — the wife of his brother-in-law, Daniel Creech. On one eventful night “the Rebel” was visiting her at the bottom of the spur when “the Metcalf brothers caught him stealing meat from the smoke house [on Meat House Cliff] to feed his small band of Rebs that were camped at Rebel Rock.”
A 1953 newspaper account in The Harlan Daily Enterprise describes what happened next: “One of the men from the southern army slipped through to Poor Fork one night [to steal from locals],” Caught red-handed in the act, “A group of angry citizens took up the chase as the ‘Rebel’ took to the mountains,”which led them to the rest of the trespassers.
“The Rebels broke into groups, ever’ man for hisself,” said local folklorist Dave Couch in a 1952 interview for Leonard Roberts’ Up Cutshin and Down Greasy, “About three of ‘em took up the spur of the point” of a rocky ridge that stuck up out of Pine Mountain. Faced with a sudden 100 foot drop off, “they had to turn and fight and risk being killed, or jump off that high clift and take their chances. Two of the Rebels turned and tried to shoot their way down the spur, but were killed and the Union men throwed the corpses off.”
The last remaining Rebel found himself “high up on the side of Pine Mountain … [on] a huge rock, larger than a building,” as the newspaper account recalled, “As the angry citizens closed around the rock, the intruder fell from the rock to his death.”
“Ambrose Metcalf is said to have threw him off and killed him,” with the help of his brothers, Adrian and James, said Ambrose’s great-grandson Kellis Metcalfe. The “six other Confederate troops,” who “were never accounted for either,” had their bodies thrown into the numerous deep crevices that pocket Pine Mountain.
David Couch also told a similar story, “They say the frames of them dead Rebels laid up there in the crevices till the meat dropped offen their frames. Nobody would take a chance to bury ‘em afeared somebody would think they favored the otherside.”
Probably out of insistence from their sister Nancy, the three Metcalfe brothers are said to have hauled Tom Crupper’s body to the other side of Rebel Rock, thrown him into a crevice, and covered him with rocks. His remains are located 100 yards uphill from the Metcalfe cemetery. Crupper and the other Rebels’ “thug bones” are still up there, said Kellis Metcalfe.
Shades of Gray
“Captain” Crupper’s men might or might not have been in military service at the time of their death. They could have been a cast of outlaws, guerrillas, scouters, deserters, and outliers hiding up in the mountains and preying on others for food. In the eyes of most Kentucky Unionists during the war, these “Rebels” were indistinguishable from Confederate soldiers since both robbed and murdered innocent civilians while wearing ragtag uniforms and falsely claiming authority. Long after Lee’s surrender at Appomattox, these bands — now without a cause to hide behind — continued to plague Kentucky.
The most notorious of Harlan’s guerrilla “captains” was “Devil Jim” Turner who was the nephew of the largest slave owner in the county. He robbed from Southern sympathizers while his “Rebel” brother, who rode with him, stole from Unionists. Devil Jim is best remembered for raping his own aunt (or cousin), murdering his Confederate cousins — the Middletons — and torching the county courthouse in the later half of the war. Like Crupper, he also served in the 49th Kentucky Mounted Infantry Regiment before deserting in May 1864 and returning to Harlan to lead a guerrilla band.
A member or ally of the Loyal League — an Unionist, pro-Republican Party paramilitary — following the war, Devil Jim Turner’s career as an outlaw continued until 1872 when he was sent to the state penitentiary for murder. Released in 1891, he moved out west to Toledo, Washington with one of his sons. He died there in 1910 when he suffered a stroke and fell into a hot stove.
Five years after Tom Crupper’s death at Rebel Rock, his widow and daughter are listed on the 1870 census as still living in Poor Fork with Ruth’s mother, her sister, and a 2 month old baby. Their neighbors still included Daniel B. Creech, his wife Nancy, and four children, including Mary Creech who was born in May 1865. Nancy’s brother James Metcalfe and his family also lived nearby. The effect that Crupper had on the relationships between husband, wife, and the related neighbors in wake of the war can only be imagined.
As to whether Nancy Metcalfe’s marriage ended because of Crupper, it is not known. Nancy Metcalfe (b.1841) might have passed away while still married to Daniel Creech (1840–1923) because her husband had remarried by 1876 and there are no further census records of her. Some genealogical websites and records actually list Crupper as Nancy’s first or second husband! Ruth Creech (1843–1937), Crupper’s widow, also eventually remarried to a man named Benjamin Shackleford.
It might be more than just a coincidence that Sarah Melissa Crupper (d. 1920), the daughter of Captain Tom Crupper, married Devil Jim’s son, James C. Turner, Jr. on June 30, 1880. For the 1890 census, Sarah listed Washington as the place of her father’s birth. His POW records list Alexandria County, Virginia. Both are correct since Alexandria County [now Arlington] was the southern part of the District of Columbia until 1846.
Adrian (1826–1892+), Ambrose (1829–1907?), and James Metcalfe (1839–1919) — the three Unionist brothers responsible for the naming of Rebel Rock — were all fortunate to survive the Civil War and live to old age. Adrian Metcalfe’s house was later moved to Pine Mountain Settlement School where it still stands at the entrance of the school. All three Metcalfe brothers are believed to be buried in their family cemetery off State Highway 522.
Ghosts of the Civil War
The spectre of the Confederacy returned to Rebel Rock on June 29, 1924 when 3,000–5,000 people converged on the Metcalf cemetery to pay tribute to fallen Ku Klux Klan (KKK) member and policeman Jesse James Saylor (1891–1923).
Saylor, a grandson of Union veteran James Metcalf, had been killed while trying to arrest a black man at Loyall the previous Christmas night. It might seem strange that a grandson of an Union veteran would join a white supremacist fraternal order named after the original Southern terrorist group that was founded by Confederate veterans in Tennessee in late 1865 to target white Unionists and blacks.
This revived Klan had been founded in wake of the success of the racist pro-Confederate and pro-Klan film TheBirth of a Nation (1915), which was directed by fellow Kentuckian, D.W. Griffith. The appeal of this modern Klan was not limited to American Southerners and, before the 1920s were over, more than 4 million white Protestants in Canada and the U.S. had joined its hooded ranks. However, it wasn’t until a nighttime cross burning on a hill overlooking the county seat of Harlan in May 1923 that the so-called “Invisible Empire” made its presence be known in the county.
A man of the law, Saylor, might have been attracted to the revived Klan’s opposition to bootleggers during Prohibition. After all, Saylor’s cousin Deputy Sheriff Moss J. Metcalf likewise died in the line of duty in 1927 as did County Sheriff Ambrose Metcalfe who was assassinated by bootleggers in 1949.
The Harlan Enterprise newspaper reported on the spectacle of Saylor’s tribute. 60 years after Crupper’s band were chased to their deaths by the people of Poor Fork, their descendants were clearly more welcoming for the Rebels’ ghoulish successors whose white, hooded masks and robs symbolized the vengeful spirits of the Confederate dead from the Civil War:
“ The train bearing the crowd contained sixteen coaches and nine cabooses, and from those that attended it was reported that it was crowded to capacity. A huge cross was hoisted on both the pilot of the engine and the rear of the train.”
“Reaching Nolansburg, a parade was formed by Klansmen and Klanwomen, clothed in the regular robes of the organization, and marched to the grave of their fallen brother. A huge monument was planted at his grave, bearing his name, the time of death and his Klan number, which was 400 [sic]. The grave was banked with rare flowers.”
“Following the laying of the stone, an address was delivered by Rev. N. E. Lougher of Paris, KY; Rev Lewis Lyttle, of Wallins Creek, lead the singing.”
“More than two hundred robed Klansmen and almost as many women took part in the ceremonies, while a vast thong from all over the county looked on. It was one of the largest gatherings of its kind ever witnessed in Harlan County, being variously estimated from 3,000 to 5000. Rev. Lougher explained to the gathering, the principles of the Knights of the Ku Klux Klan and its 1924 program. This was the first public clan address in the county.”
Another Klan funeral was held three years later in March 1927 at the Nolan Cemetery just north of Rebel Rock when the cousin of Crupper’s wife, Martha Creech Nolan (b. 1841), was laid to rest. The widow who had married two Union soldiers during the Civil War — one of them (Joseph Nolan) being an associate of Devil Jim Turner — had requested six white-robbed Klansmen from Loyall be her pallbearers.
This vehemently anti-Catholic, antisemitic and anti-immigrant “second” Klan fortunately failed to catch on in the Commonwealth where efforts led by political elites curbed Klan rallies and parades. But in Harlan they were made up of “nice people” — including unionized coal miners and preachers.
“[Many of] them, that I knew that was Ku Kluxers, were preachers,” remembered coal miner Tillman Cadle (1902–1994) in Alessandro Portelli’s They Say in Harlan County: An Oral History. “Preachers, they were all for it, and a lot of people was fooled by it — they didn’t know what the Ku Klux was. Ministers would make out that they was against anything that was ungodly and that the Ku Klux was going to help straighten things outs.”
“The biggest thing they did was that somebody got drunk and and beat their wife up, then the Klan would go in and give ‘em a beating and tell them not to be bothering her anymore,” zinc miner and poet Mildred Shackleford (b. 1950) relayed what a 1920s black coal miner had told her in They Say in Harlan County: An Oral History. “And they kept a lot of laws in coal camp towns, but they wasn’t based upon doing bad things to black people.”
The Ku Klux Klan War of the 1890s
Eastern Kentucky had historically been a holdout of “Klan” activity in the late 19th century long after the terrorist group had faded from existence elsewhere in the South.
While nearby Breathitt County’s Klan — made up of Democratic voting Confederate veterans — murdered white Unionists, blacks and their Republican descendants through the 1890s, the so-called Klan in Harlan and neighboring Letcher County in the 1890s largely sought to “enforce morality” by robbing, raping and whipping “lewd” women — including alleged prostitutes.
This incarnation of the Klan — centered in Letcher and Pike Counties — was led by brothers John and Noah Reynolds and their cousin Morgan Tillman Reynolds (1874–1957). While John and Noah’s father had served in the Confederate Army before joining the Union Army, Morgan’s father is said to have bitterly hated the “Rebels” for stealing his shoes.
The murder of a Letcher County sheriff in 1900 and later Jemina Osborne Hall and her son in 1901 led to arrests and expulsion of the masked “youthful reformers” from the state.
The crackdown on the KKK was led by Deputy Sheriff “Devil” John Wright (1844–1931) — a Democrat, polygamist, brothel punter, moonshiner, circus performer and serial killer in his own right — who served in both armies during the Civil War but made a small fortune by repeatedly joining and deserting the Union Army as a paid substitute for wealthier drafted men.
“We made the mistake of whipping one of Bad John’s lewd women and he damn near killed every one of us because of it,” recalled Klansman and future Prohibition agent and sheriff himself, John D.W. Collins (1880–1973), in Hary Caudill’s The Mountain, the Miner and the Lord.
Nearly thirty years later in November 1927, 200 unmasked men broke into Letcher County’s jail in Whitesburg and kidnapped Leonard Woods, a black coal miner accused along with two black women of murdering a white foreman. Little surprise that Morgan Tillman Reynolds was the Republican sheriff at the time.
Woods was led away with a chain around his neck and taken by the lynch mob to the state line where he was then shot to death by “a half circle of rifles”. His body was then placed on a platform recently erected for the dedication ceremonies of the opening of the Kentucky-Virginia highway and doused with gasoline.
“Roaring flames mounting from the top of Cumberland mountain signaled the death of Leonard Woods,” The Associated Press grimly reported.
Racial lines and picket lines
The Klan attempted another revival in Harlan in the 1970s, which culminated in 1975 with a cross burning and a speech by “Grand Imperial Dragon” — and future Louisiana state representative and candidate for governor — David Duke in the town of Verda.
According to black resident Julia Cowans (1925–2010) in a 2002 interview with the Kentucky Civil Rights Oral History Project, local boys who had recently graduated from high school — both black and white — came home from their jobs up north upon hearing about the Klan rally, stockpiled ammunition, armed themselves and hid up in the treeline in case trouble broke out with the Klan.
Just a few years before in 1971 or 1972, a local black woman had been lynched while in police custody. Kevin Greer (b. 1960) recalled the brutal murder of his cousin in They Say in Harlan County: An Oral History:
“They hung her up on Pine Mountain because she was with a white man. What happened is, she went with a well-known white gentleman from downtown — he was one of the upper class — and he must’ve felt alone, because he would come over all the time. They arrested her for prostitution, but she never made it to the jail. And the next morning we get news that she was found hung and burnt.”
According to New York film director Barbara Kopple, a great many of strikebreaking “scabs”, coal operators and state troopers joined the Klan following the bloody 1972 strike led by the United Mine Workers of America (UMWA) against Duke Power that was depicted in Kopple’s 1976 documentary, Harlan County, USA.
Kopple said in a 1980 interview in Alan Rosenthal’s The Documentary Conscience: A Casebook in Film Making that a leading labor activist was arrested for allegedly kidnapping a wife of a Klansman. Kopple claimed that “during her time she was in jail, the Klan had paramilitary rallies and the principal of the local high school had the girls in the home economics making gowns and hoods for the Klan.”
According to Kopple, the 1976 screening of her documentary in Harlan had to be an “armed screening” after a goat with the initials of KKK was found hanging at the place where the film was going to be shown to miners and their families. Likewise a “revival meeting” soon thereafter had to be called off after the Klan threatened to firebomb the hosting “revival center”.
“A couple of black Cadillacs pulled up with high-powered rifles and stayed parked outside the whole time,” said Kopple. “So the fight still goes on.”
The memories of the Civil War and the Klan have long since faded in Eastern Kentucky but the legend of Rebel Rock still looms large. Few signs — aside from hillside gravestones — otherwise remain. But somewhere 100 yards uphill from the Metcalf cemetery, still lays the Reb spy and Union deserter Tom Crupper in his forgotten and unmarked tomb.
Below we have a list of historic videos that will give you better insight into the rural county of Harlan Kentucky . To best understand rural America is to understand their history from the 1900s till about 1980s Harlan Countians was groomed by big coal to be their labor force. There is still no major companies in Harlan other than Walmart or dollar tree and these can only provide so many jobs. The videos below give you a good idea of the history of Harlan we will and content as we find it.