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1817 - Madison Co., Fast-talking Harry
Just after the New Year, 1817, 22-yr-old Harry took his leave from Madison County slaveholder John Duncan. He was described as 5'9" tall and stout, with round features. Harry was a very fast talker as well. Up to $50 was offered for his return.
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1809 - Madison Co., The "Theft" of Lorry
18-yr-old freedom seeker Lorry disappeared from Madison County slaveholder Hiram Biggerstaff just after Christmas, 1809. There was an assumption that she was "stolen" and may be disguised as a man. She was described as tall and slim, with pierced ears and "very neat made." She was well dressed and "thinks herself much of a lady." $50 reward was offered for her return.
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1826 - Madison Co., Despite Injury, Freedom Seeker Takes Flight
An unnamed 21-yr-old man, held by slaveholder Green Clay of Madison Co., escaped on Dec 15, 1826. He had an injured ankle that was "put out of place" causing him to limp. The man was also skilled in making "coarse shoes." A reward of up to $50 was offered for his return.
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1816 - Madison Co., Escape of Pompey
Pompey, described as about 24-yrs-old, six feet tall with dark, smooth skin, escaped Madison Co. slaveholder Thomas Grubbs on the 20th of April, 1816. a reward of up to $50 was offered for his return
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1819 - Madison Co., Skilled Freedom Seeker
Felp, a freedom seeker who was about 30-35 yrs old, escaped Madison Co slaveholder James Collins on July 14, 1819. He was described as a "first rate workman" who was a skilled currier and tanner. Felp, who was able to read and write, was brought to Kentucky from Madison County, VA in 1817. A reward of $200 was offered for his return.
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1827 - Madison Co., Three Men, Two Women and Two Infants Flee Bondage
On October 27, 1827 a group of freedom seekers escaped from four Madison County slaveholders. The group consisted of George and his wife Milly and their three-month-old twins; Ben and his wife Hannah, who was pregnant and another man named George. $250 was offered for the group or $50 a piece for the adults individually.
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1827 - Madison Co., Brief Freedom for Squire
Freedom seeker Squire escaped from Madison County slaveholder Green Clay on Sept 22, 1827. Green Clay was the cousin of Henry Clay and father of emancipationist Cassius Clay. Squire was about 30 yrs old when he escaped and Clay offered a $50 reward for his return. He was described as about six feet tall, with a scar that ran from his mouth back towards his ear. He also was missing a part of his ear, lost in a fight. It appears that he was recaptured, as Squire was listed in Clay's will (Sept 8, 1828) along with several other enslaved people. All were to be sold out of the state, never to return. Since Clay appeared to have some emancipationist leanings himself, this may be an indication that the sale of Squire and others was retribution for running away.
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1808 - Madison Co., The Disappearance of Jerry
In late January, 1808, Madison County slaveholder Humphrey Jones realized that 23-yr-old Jerry had escaped him. He placed an ad offering a $50 reward for Jerry's return. Jerry was described as about 5'10" tall with a scar on the back of one thigh. He was wearing leather breaches and an yellow hunting shirt when he escaped.
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1826 - Madison Co., Escape of Well-Read William
On December 10, 1826, Madison County slaveholder William Barnett discovered that 22-yr-old William had escaped from his property near Silver Creek. In an ad placed three days later, William is described as "stout made; nearly 6 feet high" and it is revealed that William can also read and write and would likely head for Ohio. A reward of $50 was offered for his return.
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1795 - Madison Co., A Pair of Freedom Seekers
In March 1795, Lewis and Harry escaped from Madison County slaveholder William Robinson. 21-yr-old Lewis was described as of a "yellow complexion," about 5'6" tall with a large scar on the inside of his right finger and a scar on his thigh from a burn. 19-yr-old Harry was described as about 5'5" tall and having a "rather dark complexion. Fifty dollars reward was offered for both Lewis and Harry or $25 for either alone.
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1798 - Madison Co., Nat and Ephraim Steal Away
Freedom seekers Ephraim and Nat escaped together from Madison County slaveholder William Walker on September 12, 1798. Ephraim, about 22, was approximately 5'9", with a "yellow" complexion. He had lost about half of one foot and several toes from the other as a result of frostbite. Nat had a dark complexion, was about 22 yrs old, and was somewhat smaller than Ephraim. A reward of $10 was offered for their return.
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1797 - Madison Co., What Happened to Wat?
Wat, a 20-year-old freedom seeker, escaped Madison County slaveholder Samuel Gilbert some time in mid-March, 1797. Wat was described as abut 5'7" tall, smart and active, with "long nappy hair," wearing buckskin breeches and hemp linen. A twenty dollar reward was offered for his return.
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1808 - Madison Co., James Trades Enslavement for Freedom
In June, 1808, Madison County slaveholder Richard Oldham offered $100 reward for the return of James, a 35-year-old man who was a "remarkably fast talker" and "fond of trading." James was about six feet tall, thin and had a beard with a few grey hairs in it. In 1808, $100 was an unusually high reward.
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1823 - Madison Co., Why Peter Ran
30-yr-old Peter was captured and jailed as a "runaway" in Breckinridge County on Sep 24, 1823. He named his slaveholder as James Brassfield of Richmond, Ky. Peter's description shows evidence of violence: one of his front teeth was knocked out and he had a "number of scars on his hips, back and shoulders which appear from being severely whipped." The jailer's mandatory ad placement was intended to bring forth the slaveholder to claim Peter and pay expenses of his confinement.
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1821 - Madison Co., Free Toney's Brother Lot
On Sep 20th, 1821, 30-yr-old Lot escaped Madison County slaveholder William Williams. It was believed that he may have had help from a brother, Toney, who was a free man, who may have given Lot his own papers to help him. A $50 reward was offered for Lot's return.
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1827 - Madison Co., Harry and Jasper Head for Freedom
Slaveholders Samuel B Taylor and R. Cox, both of Madison county, offered a reward of $100 for the return of Harry and Jasper, who escaped together in the fall of 1827. Jasper was 28-yrs-old, of "yellow" complexion and about 5'10"; Harry was about the same height, of a dark complexion and was about 30 years old. It's unclear which slaveholder claimed whom.