By the time his most ambitious speculation scheme – his contract with John May and Samuel Beall – collapsed in late 1786, Imlay must have realized that his days as a land-jobber were well-nigh over. His curriculum vitae in general did not look too good at this point in his life. Since his early twenties, he had had a brief but undistinguished career in the Revolutionary army; he had emerged relatively unscathed from the breakdown of socioeconomic order in wartime New Jersey, though with little to boast about, either; and he had been an enterprising land-jobber in Kentucky, albeit a spectacularly unsuccessful one. Now at thirty-two, he was down and out, and had run out of obvious career options. Having defaulted on so many debts, cheated so many people out of their land and property, and ignored so many court summonses, there was virtually no place left in the union for him to hide, let alone to make an honest living. It is highly unlikely that he ever went back to Kentucky after he left the district in November 1785. There were no sightings of him there throughout the spring and summer of 1786, and, besides, the legal and financial fallout of the collapse of the deal with Beall and May in the autumn of that year rendered any thought of resuming trade in Kentucky impracticable. Nor does he seem to have visited Virginia again after December 1786, when he wrote his famous farewell note to Daniel Boone during a brief visit to Richmond. The prominent Virginia lawyer and Revolutionary-era diplomat Arthur Lee – who had every reason to find Imlay after the latter had first failed to deliver the patents to the 4,023 acres he had sold to Lee back in September and who had then reneged on his legal obligation to offer him land in as good a situation and of the same quality – could not find a trace of Imlay anywhere in Virginia despite his best efforts.