In the Wailes v. Smith case of 1894, the U.S Supreme Court was tasked with determining whether a will that left property to an individual and their heirs, but stipulated it could not be sold or mortgaged until after the death of said individual's last surviving child, created a fee tail estate (a type of inheritance which must pass down directly through family lines) or a life estate followed by contingent remainders (an interest in property that depends on some event occurring). The court ruled in favor of Smith, deciding that under Maryland law at the time when the will was written - despite its restrictive language - it did not create a fee tail estate. Instead, they found it established life estates for each child living at testator’s death with contingent remainder interests for their children. This decision clarified how such cases should be interpreted moving forward.

In the dissenting opinion for Wailes v. Smith, Justice Brewer argued that the majority's decision to deny a writ of error was incorrect. He contended that there were indeed federal questions involved in this case and thus it should be under Supreme Court jurisdiction. Specifically, he pointed out that whether or not a state law impairs the obligation of contracts is undeniably a federal question as it involves interpretation of the Constitution’s Contract Clause (Article I, Section 10). In his view, if any part of an individual's claim rests upon such constitutional grounds then they have every right to bring their case before this court regardless if other non-federal issues are also present within their claim. Therefore, he disagreed with dismissing plaintiff’s appeal on procedural grounds without addressing these substantive constitutional claims.