You may recall that David T. McNeff's bio says John T. disappeared in 1802. I recently had the chance to travel briefly to New Orleans, and though I wasn't able to find newspaper's from the period - a trip to a State museum did set me thinking about the Louisiana Purchase.
Tensions seemed to be running high over US access to the port in New Orleans. In April of 1802, Thomas Jefferson wrote to the US ambassador to France:
Every eye in the U.S. is now fixed on this affair of Louisiana. Perhaps nothing since the revolutionary war has produced more uneasy sensations through the body of the nation.
In October, Spain had signed Louisiana over to France, and the port of deposit was closed to American trade.vThere's a nice summary on the Louisiana Purchase here.
Two lines of query present themselves:
1. What is the most likely time of year for John T. to have departed Kentucky by flatboat and when would he have arrived in New Orleans?
2. It's time to read an authoritative book on the Louisiana Purchase to better understand the political atmosphere of that summer.