The tax records indicate that John and his family lived near the town of Brownsburg. On March 18, 1822, John was taxed for a family of two white males over 16, with two horses, $ 0.27.
There are no records in Amherst or Rockbridge counties to indicate that John Bobbitt owned any land. In fact the records indicate that John Bobbitt was a sharecropper for wealthy farmers in Rockbridge County. There is a deed recorded in Rockbridge County in Book M, page 524, on June 19, 1821, which gives a story concerning the labor of John Bobbitt.
"Indenture between John Bobbitt of Rockbridge County and John Templeton, trustee. Witnesseth that John Bobbitt in order to secure payment of a debt of $ 63.00 due by John Bobbitt to Henry McCormick Junior, John Bobbitt hath granted unto the trustee all the wheat, rye, and corn on James McDowell's land, now in the ground, and belonging to the said Bobbitt, also one bay horse, seven hogs, and seventeen sheep, with all the estate right .......
John J. Templeton
The above debt was paid. John Bobbitt again was faced with a debt to Robert McChesney of Rockbridge County, and again had to offer his crops as security, on April 12, 1823. John was attempting to purchase land from the firm of Alexander and Irvine, but was having trouble in meeting the payments. On April 17, 1823, this record in Deed Book N, page 387, tells the story.
"Indenture between John Bobbitt and William C. Lewis, whereas John Bobbit is justly indebted to Alexander and Irvine, the sum of $ 53.77, which debt he is desirous to secure, Alexander and Irvine, and John Bobbitt, hath conveyed this day to Wm. C. Lewis, I grey mare with colt, 15 sheep, 3 cows, one steer, 20 hogs, 1200 pounds of tobacco, and proceeds of eleven acres of wheat now in the ground, proceeds of 18 acres of corn which I am about to plant on the plantation whereon I now live, if I defalt the property will be advertised by A and I at some place near the town of Brownsburg.
Wm. C. Lewis
Andrew H. Jordan
J. A. McClung