April 19 is a pretty bad day in U.S. history generally. In 1775, the Revolutionary War started with a rout in Lexington, Massachusetts, just a few minutes by car up Massachusetts Avenue from my childhood home in neighboring Arlington, then Menotomy. 700 British troops, having shot up that hamlet and its defenders on the way, found 77 armed minutemen under Captain John Parker opposing them on Lexington Green, now a large traffic circle. It took a just few minutes to kill enough of the barely trained Colonists for the ragtag army to disperse, but the British marched into a much larger force at nearby Concord Bridge, and a much worse result for the Empire. In 1993, a botched siege of the Branch Davidian compound in Waco, Texas ended with 22 children and almost 80 adult religious cultists burning to death. In 1995, the U.S. was introduced to domestic terrorism on a grand scale with the Oklahoma City bombing. But none of those events create the ethics trauma of considering a little noted financial transaction between the former third President and the newly sworn in fourth.
On April 19, 1809, Thomas Jefferson, seemingly always lacking cash, prepared a contract to transfer ownership of an indentured servant with the ironic name of John Freeman to freshly installed President and fellow Virginian James Madison.