While the owner had absolute powers of disposal of his own slaves he could not draw up a will of prospective freedom which would hold in spite of the rights of his heirs. If a master desired to be very lenient with his servants, he had to make their freedom absolute and in writing. This was well brought out in the case of an apparently kind-hearted Kentucky slaveholder who provided in his will that his slaves were to select their own master without regard to price. They chose as their future owner a man who did not need them, but who offered to take them at about half their real value. The court held that in such a case the executor was not bound to accept the offer, since the interests of those entitled to the proceeds of the sale, as well as the desire and comfort of the slaves, were to be regarded.[344] Another owner had the right idea, but defeated his own intentions by willing all his forty slaves to the Kentucky Colonization Society. The court held that such an act by no means freed the slaves and that by the laws of the State until they were free they could be hired out and the proceeds considered as a part of the estate.[345]
As in all border States there were many legal battles for freedom, which involved the question of residence on free soil. These cases were largely concerned with the question of the right of a citizen of Kentucky to pass through a free State on business or pleasure attended by his slaves or servants without losing his right of ownership over such slaves. The principle involved was early considered in the Kentucky Court of Appeals and faithfully carried out in succeeding generations, viz.: that a "fixed residence" or being domiciled in a non-slaveholding State would operate to release the slave from the power of the master; but that the transient passing or sojourning therein had no such effect. In an early case in 1820 involving a suit for freedom the court held that a person of color from Kentucky who was permitted to reside in a free State could prosecute his right to freedom in any other State. It was held to be a vested right to freedom, which existed wherever he went.[346] In another instance an owner permitted his slave to go at large for twenty years, but the court held that that alone did not give him freedom. Still under this liberty of movement the slave went off into a free State to reside and the court held that the Negro was then free because his right grew out of the law of the free State and not out of that in which the owner resided.[347] An owner permitted his slave to go to Pennsylvania and remain there for a longer period than six months, with a knowledge of the law passed in that State in 1780, and the Kentucky Court of Appeals held that the slave was entitled to his freedom and that even if the slave had returned to Kentucky his right could be asserted there just as well as in Pennsylvania.[348] But should a slave go with his master to a free State and later return to Kentucky with him, whatever status he had then was to be determined by the law of Kentucky and not by the rule of any State where the slave might have been.[349] The fact that a slave stayed in New York for three months before his return to Kentucky, his owner knowing he was there, and making no effort to bring him away, did not give to such slave a right to freedom.[350] A slaveholder sent one of his servants over into Illinois to cut some wood for a few weeks and later the latter brought suit for freedom on the grounds of residence in a free State but the court denied any such right, since the slave returned to his master in Kentucky voluntarily.[351]