It has been a matter of debate among scholars as to when exactly Imlay appeared in the western territories of the Ohio Valley. According to his own account of it in the Topographical Description, Imlay first crossed the Allegheny Mountains ‘in March’, and, finding Pittsburgh ‘not [yet] recovered from the ravages of winter’, immediately decided to leave for the balmy climate of Kentucky, arriving at Limestone, near present-day Maysville, ‘in less than five days’. Unfortunately, he does not give us the year. Pointing out that ‘the long court record of the business and legal entanglements that marked his residence of not quite two years in Kentucky’ begins in 1784, Rusk infers that Imlay did not appear in Kentucky before the spring of that year. This date appears to be confirmed by the fact that Imlay was sworn in at Louisville as a deputy surveyor of Jefferson County under George May on 7 April 1784. However, by that time Imlay had already begun speculating in Kentucky lands. His earliest documented transaction was with the veteran pioneer and land-jobber Daniel Boone. In March 1783 Boone agreed to accept Imlay's promissory note for £2,000, to be paid in two instalments in exchange for a tract of 10,000 acres located on Hingston's Fork of the Licking River in Fayette County, which Boone had entered on 26 December the year before. Also in March 1783 Imlay purchased another 20,000 acres of land in Fayette in a transaction with Captain John Holder – a deal that, as we shall see, would go horribly sour later. On the 3 August 1783 Imlay concluded another complicated land deal with Holder's business partner Matthew Walton; this particular deal involved several thousand acres of land in Jefferson County, and would lead to a legal battle that would continue until the early 1800s, long after Imlay had left Kentucky and America.