The Winton v. Amos case in 1920 involved a dispute over land ownership between the Mississippi Choctaws and the heirs of George Winton, who had purchased lands from them. The Supreme Court ruled in favor of the Mississippi Choctaws, stating that they were entitled to retain possession of their ancestral lands despite having sold portions to non-Native individuals like George Winton. The court held that such sales were invalid because they violated federal laws prohibiting private purchases of Native American lands without congressional approval. This decision reaffirmed tribal sovereignty and property rights by emphasizing that only Congress has authority over transactions involving Indigenous territories.

In the dissenting opinion for Winton v. Amos, Justice Holmes disagreed with the majority's decision to deny Mississippi Choctaws' claim to land in Oklahoma. He argued that the Treaty of Dancing Rabbit Creek should be interpreted as granting them rights to this territory. The treaty had promised lands west of the Mississippi River if they chose to move there voluntarily, and Holmes believed it was unjust not to honor this promise simply because some tribe members remained in Mississippi instead of relocating immediately after signing. He also criticized his colleagues for ignoring historical context when interpreting treaties with Native American tribes, stating that these agreements were often negotiated under duress or misunderstanding and thus deserved a more generous interpretation favoring indigenous peoples.