After his manumission in 1819, Free Frank continued to live in Pulaski County. Many areas of the Pennyroyal remained undeveloped, and the services and commodities that pioneer blacks could provide still proved a necessary and even integral part of that region's developing economy. Through-out the 1820s Free Frank carefully expanded his business activities. Land speculation and the improvement of those holdings for sale to prospective farm settlers were added to his own commercial farming activities. His saltpeter manufactory, too, showed continued growth and became even more profitable. Perhaps it was his business success that prompted the litigation in which he and Lucy were involved from 1820 to 1827. It was common knowledge in Pulaski County that Free Frank had recently paid $1,600 for both his and Lucy's freedom. Obediah Denham, who initiated the suit against them, for $212, obviously considered the former slave solvent. Lucy's former owner, William Denham, had died intestate. His son Obediah, the appointed executor, was at that same time being sued by other heirs to the Denham family estate when he made his claim against this free black couple as a debt encumbered upon his father's estate. As the litigation proceeded, Denham's motive for the suit emerged as increasingly suspect, although when the case was initially heard it was quickly disposed of by the Pulaski County Court in Denham's favor.

When the case was first brought to the court, Lucy and Free Frank stood as co-defendants. As the case developed, two distinct issues emerged, which subsequently would be heard in the Kentucky Court of Appeals. The state's highest court made two separate determinations, the first in 1824, the second in 1827.2 As the records show, what initially brought the case to the Pulaski County Court was “an action of debt brought by the administrator of William Denham deceased, upon a sealed writing executed by Free Frank and Lucy, stipulating for the payment of two hundred and twelve dollars to the intestate.”3 In their defense, Free Frank and Lucy proffered separate pleas. Lucy's defense was allowed first. This former slave woman held that “at the time of the supposed execution of the note in writing declared on by the plaintiff, she was, and is still married to Frank, a person of color and this she is ready to verify.”4 Lucy based her defense on the rule of law offemme couverture, whereby all contracts with married women had to be made by their husbands or they were invalid and not binding upon the wives to fulfill.5 Free Frank's defense was that even though he was her husband he was not liable: he was a slave at the time the contract was made, and slaves, being legally incapacitated, could not make contracts….6