Skillern's Executors v. May's Executors was a case heard before the United States Supreme Court in 1810. The dispute centered around two executors of an estate, Skillern and May, who were both appointed by the same court to manage it. Skillern had been appointed first but then died shortly after his appointment; as such, he was replaced by May as executor of the estate. However, when Skillern’s heirs sued for their share of the estate’s proceeds from its sale, they argued that since Skillern had been appointed first and thus held title to all assets at death—including those sold during May’s tenure—they should receive their portion from those sales too. The Supreme Court ultimately sided with them in a 5-4 decision: because there is no legal distinction between an executor holding title prior to or subsequent to death (as long as they are still legally responsible for managing it), any proceeds generated while either party held title must be distributed according to law regardless of which one did so at what time.

In Skillern's Executors v. May's Executors, the Supreme Court was tasked with determining whether a deed of trust executed by William Skillern in 1790 was valid and enforceable. The majority opinion held that it was not because the deed did not contain an express promise to pay or any other language indicating an intent to create a debt obligation. Justice Story dissented from this decision, arguing that although the document did not explicitly state an intention to create a debt obligation, there were sufficient facts present which indicated such an intention existed at the time of execution. He argued that when taken together with surrounding circumstances and evidence presented during trial, these facts established beyond reasonable doubt that both parties intended for there to be a binding contract between them; thus making it unnecessary for such agreement to be expressed in writing as required by law at the time.