The barony of Draffane, in which Craignethan was located, was a property of the Black Douglases until their forfeiture in 1455. The land was granted to the Hamilton family, and in 1530 was given by James Hamilton, 1st Earl of Arran to his illegitimate son James Hamilton of Finnart. "Draffin, a strong house of the Duke's, but situate in a hole, so that it is commanded on every part, and has no ordnance." In the same month Lord Sempill now a King's man was captured and imprisoned in the castle.