In the case of Simpson v. United States (1905), the U.S Supreme Court dealt with a dispute over land ownership in Oklahoma. The plaintiff, Simpson, claimed that he had purchased a parcel of land from an individual who had received it as part of an allotment under the Dawes Act - legislation aimed at encouraging Native Americans to assimilate into mainstream American society by becoming private property owners. However, this was contested by the government which argued that such sales were prohibited until after 25 years from when they were allotted according to Section 15 of Curtis Act and hence voided his claim on said property. The Supreme Court ruled in favor of the government stating that although there was ambiguity between different sections within these Acts regarding sale restrictions, it should be interpreted in favor of protecting Native American interests. Therefore, any conveyance or contract made before completion of those 25 years would be considered null and void.

In the dissenting opinion for Simpson v. United States, 1905, Justice Holmes disagreed with the majority's interpretation of a statute that allowed for additional punishment if a crime was committed on an Indian reservation. He argued that this law should not apply to Simpson because he was tried in federal court rather than tribal court. According to Justice Holmes, applying this law in federal court would result in double jeopardy - punishing someone twice for the same offense - which is prohibited by the Fifth Amendment of the Constitution. He also contended that Congress did not intend for this law to be used as it was against Simpson and suggested that its application here could lead to absurd results where individuals are punished more severely simply based on where they commit their crimes.