In the Holloway v. Dunham case of 1897, the U.S Supreme Court ruled on a dispute involving land ownership in Oklahoma. The plaintiff, Holloway, claimed that he had purchased a piece of property from an individual who had received it as part of a government allotment to Native Americans. However, under federal law at that time (the General Allotment Act or Dawes Act), such lands were not allowed to be sold for 25 years after being allotted. The defendant, Dunham, argued this point and asserted his own claim over the property based on subsequent purchase from another party. The court sided with Dunham and upheld the restrictions imposed by federal law regarding sale of native allotments within 25 years period. It stated that any contract attempting to sell such land before expiration was void due to its violation against public policy designed to protect Native American interests. This decision reaffirmed federal authority over state laws concerning Native American affairs and emphasized protection for indigenous people's rights in their dealings with non-indigenous individuals or entities.

In the dissenting opinion for Holloway v. Dunham, Justice Harlan argued that the majority's decision was inconsistent with established legal principles regarding property rights and contracts. He contended that Mr. Holloway had a legitimate claim to his late wife's estate because he had made significant financial contributions towards its acquisition during their marriage, despite not being named in her will or any deeds of trust related to the property. Furthermore, Justice Harlan disagreed with the majority's interpretation of Mrs. Holloway’s intent when she purchased and managed her properties separately from those of her husband; he believed it did not necessarily mean she intended to exclude him from inheriting them upon her death.