In the case of Catharine Hill v. Joseph W. Tucker, Executor of Abner Robinson, Deceased, Hill brought a suit against Tucker for damages resulting from an alleged breach of contract between her and Robinson before his death. The court found that there was no evidence to support Hill's claim that she had entered into a valid agreement with Robinson prior to his death and thus dismissed her complaint on the grounds that it could not be enforced after his passing. Furthermore, they held that even if such an agreement did exist at one point in time, it would have been void due to its illegality under state law as contracts involving slaves were prohibited by statute at the time. As such, the Supreme Court ruled in favor of Tucker and denied any compensation or relief for Hill's claims against him as executor of Robinson’s estate

In the case of Catharine Hill v. Joseph W. Tucker, Executor of Abner Robinson, Deceased, the Supreme Court was asked to decide whether a deed from an executor could be considered valid if it had not been approved by the court overseeing the estate. The majority opinion held that such deeds were invalid and thus unenforceable in court; however Justice McLean dissented on this point. He argued that there was no legal precedent for requiring approval from a probate court before an executor's deed could be enforced in civil proceedings and that any other interpretation would lead to absurd results as it would place too much power into the hands of courts with little oversight or accountability. Furthermore, he noted that allowing such deeds without judicial approval would provide greater protection for creditors who may otherwise have difficulty collecting debts owed by deceased individuals due to their lack of capacity after death. Ultimately, Justice McLean concluded his dissent by arguing against placing undue restrictions on executors' ability to act within their fiduciary duties when settling estates and urged caution when interpreting laws related thereto so as not to unduly burden those tasked with carrying out these important responsibilities