In the case of Richard R. Keene v. The Heirs of Daniel Clark, Keene argued that he was entitled to a tract of land in Kentucky which had been granted by Virginia to his ancestor prior to Kentucky becoming a state. The court found that while Virginia did have authority over the area at one point, it no longer held any jurisdiction after Kentucky became an independent state and therefore could not grant titles or deeds for lands within its borders. Furthermore, since there were no laws in place when Kentucky declared independence from Virginia regarding pre-existing grants made by the former government, those claims were invalidated as well and thus Keene's claim was denied.

In Richard R. Keene v. The Heirs of Daniel Clark, the Supreme Court was asked to decide whether a deed from one party to another was valid and enforceable when it had been signed by an attorney-in-fact on behalf of the grantor but not acknowledged or proved before any officer authorized by law. In a dissenting opinion, Justice McLean argued that there were two separate issues at stake in this case: firstly, did the power of attorney authorize its holder to execute deeds; and secondly, if so, could such deeds be enforced without being acknowledged or proven? Justice McLean believed that although it may have been within the scope of authority granted by the power of attorney for its holder to execute deeds on behalf of his principal (the grantor), these instruments should still be subject to proof as required under state law in order for them to be legally binding upon both parties involved. Therefore he concluded that since no such proof had taken place here, then this deed should not have been held valid and enforceable against either party involved in this dispute.