Ditcher was an enslaved man in 1800 and the property of the estate of William Bowler, of Caroline County. Contemporary documents refer to him as Jack, Jack Bowler, Jack Ditcher, or Jack Bowler alias Jack Ditcher, the last suggesting that because of the work he did he may have been generally known as Jack Ditcher rather than by the name of his owner’s family. It is possible that the administrator of the Bowler estate hired the valuable workman to people who needed someone to dig ditches. The earnings would have gone to support the estate and its orphan children, and Ditcher might have worked and made acquaintances at a number of places, some perhaps far from his usual place of residence. The administrator of the Bowler estate described him in 1800 as about twenty-eight years old, with a scar above one eye and very long hair worn in a queue in the back but twisted on the sides of his face. At about six feet, four or five inches tall, Ditcher was “perhaps as strong a man as any in the state.” He was probably.
In the spring of 1800 Ditcher became involved with Gabriel, an enslaved man who was planning to lead an insurrection. One conspirator later testified that Ditcher had declared that they had as much right to fight for their liberty as any men and another that Ditcher had acquired gunpowder for the purpose of fighting the white people. A funeral that several conspirators attended in August provided cover for a meeting at which they were able to complete their plans without arousing white suspicions. They intended to seize the penitentiary in Richmond and the magazine where weapons were stored at the state Capitol. Gabriel and his men enlisted new followers from the enthusiastic crowd, and Ditcher offered to lead the insurrection as its general. The men voted instead that Gabriel lead, although one of the conspirators later testified that Ditcher was made second in command. They then set the date for the insurrection, and the leaders, including Ditcher, met again on August 21 and 25 to make final plans.
During the morning of the appointed day, August 30, 1800, one of the conspirators and another enslaved man informed Mosby Sheppard, the owner of one of them, of the conspiracy. He alerted Governor James Monroe, but a tremendous rainstorm that night washed out bridges and cut off access roads and lines of communication and the insurrection did not begin. The governor called out the militia, and within six weeks Gabriel and about two dozen other men had been arrested, tried, and hanged. The governor issued a proclamation on September 9, 1800, offering a $300 reward for Ditcher’s capture and later that month published a detailed physical description of him. After evading capture for an additional month, Ditcher surrendered near Richmond on October 8 or 9.
A Henrico County court of oyer and terminer tried Ditcher on October 29, 1800. Three enslaved men testified against him. At an earlier trial, one of the conspirators had also stated, without offering any proof, that Ditcher knew the names of two white Frenchmen who had joined in the conspiracy, a mystery that the trials and investigations never solved. Ditcher was convicted and sentenced to be hanged on the second Friday in November.
By that time, the governor and others were reluctant to hang even more men. The General Assembly commuted the death sentences of Ditcher and eight other men to transportation out of the United States. On January 26, 1801, the state sold them to slave traders for that purpose and later paid William Bowler’s estate $400 to compensate it for loss of its slave property. The two traders transported the nine men across country to Point Pleasant, on the south bank of the Ohio River, where two of them escaped north into the Ohio territory. The traders recaptured them, wounding one of the slaves in the process, and descended the Ohio River to the Mississippi. They crossed into Spanish territory and sold all the men on credit at a low price, news of the conspiracy having reduced their market value. The traders lost their investment and evidently were never paid. Nothing else is known about Jack Ditcher, who presumably lived the remainder of his life and died somewhere in the Mississippi River valley.