In September 1786 Imlay appeared before Edward Shippen and Plunkett Fleeson, justices of the Court of Common Pleas in Philadelphia, in order to acknowledge and confirm the written indentures by which he had earlier agreed to sell nine tracts of land in Jefferson County, amounting to 15,043 acres, to the former Continental Navy privateer Colonel Silas Talbot, then of Philadelphia, for £750 Pennsylvania paper money and 12,771 Spanish silver milled dollars. The Talbot transaction had been unusual for Imlay for at least two reasons: the bulk of the land involved in the deal exchanged hands for hard silver instead of the usual promissory notes, and Imlay actually held legal title to all of the lands for which he received the silver dollars. In fact, he had specifically travelled to Richmond in December 1785 to be able to collect the patents for the nine tracts in person. Imlay must have had a very good reason for disposing of the bulk of his patents – the only real assets he ever got out of his land-jobbing activities – in a single transaction. Evidently, the opportunity had arisen to invest his nest-egg in a venture that was more lucrative and less risky than the land-jobbing business had been. That venture turns out to have been the triangular trade, and the man who introduced him to it was none other than the Revolutionary War hero Silas Talbot.

Congress having retired him from the Continental Navy as a lieutenant colonel without pay on 1 January 1782, Silas Talbot was eager get back into the world of business as soon as the Revolutionary War ended.