Among his slaves were some that were too unruly to be managed by ordinary means.  In the early seventies he had such a one on a plantation in York County, Will Shag by name, who was a persistent runaway, and who whipped the overseer and was obstreperous generally.  Another slave committed so serious an offense that he was tried under state law and >vas executed.  When a bondman became particularly fractious he was threatened with being sent to the West Indies, a place held in as much dread as was “down the river” in later years.  In 1766 Washington sent such a fellow off and to the captain of the ship that carried the slave away he wrote: 

“With this letter comes a negro (Tom) which I beg the favor of you to sell in any of the islands you may go to, for whatever he will fetch, and bring me in return for him

“One hhd of best molasses

“One ditto of best rum

“One barrel of lymes, if good and cheap

“One pot of tamarinds, containing about 10 lbs.

“Two small ditto of mixed sweetmeats, about 5 lbs. each.  And the residue, much or little, in good old spirits.  That this fellow is both a rogue and a runaway (tho he was by no means remarkable for the former, and never practiced the latter till of late) I shall not pretend to deny.  But that he is exceedingly healthy, strong, and good at the hoe, the whole neighborhood can testify, and particularly Mr. Johnson and his son, who have both had him under them as foreman of the gang; which gives me reason to hope that he may with your good management sell well, if kept clean and trim’d up a little when offered for sale.”

Another “misbehaving fellow” named Waggoner Jack was sent off in 1791 and was sold for “one pipe and Quarter Cask” of wine.  Somewhat later (1793) Matilda’s Ben became addicted to evil courses and among other things committed an assault and battery on Sambo, for which he received corporal punishment duly approved by our Farmer, whose earnest desire it was “that quarrels be stopped.”  Evidently the remedy was insufficient, for not long after the absent owner wrote: 

“I am very sorry that so likely a fellow as Matilda’s Ben should addict himself to such courses as he is pursuing.  If he should be guilty of any atrocious crime that would affect his life, he might be given up to the civil authority for trial; but for such offenses as most of his color are guilty of, you had better try further correction, accompanied by admonition and advice.  The two latter sometimes succeed where the first has failed.  He, his father and mother (who I dare say are his receivers) may be told in explicit language, that if a stop is not put to his rogueries and other villainies, by fair means and shortly, that I will ship him off (as I did Waggoner Jack) for the West Indies, where he will have no opportunity of playing such pranks as he is at present engaged in.”