In the case of Gillespie v. State of Oklahoma in 1921, the U.S. Supreme Court ruled on a dispute involving oil and gas rights on Native American tribal lands. The state of Oklahoma had imposed taxes on an oil company operating under leases from members of the Osage tribe, which was contrary to federal law that exempted such operations from state taxation. The court held that while states have broad powers to tax businesses within their borders, these powers do not extend to activities carried out under federal authority or protection - in this case, mineral extraction on tribal land overseen by the Bureau of Indian Affairs (BIA). Therefore, it was decided that Oklahoma's imposition of taxes violated federal law and were invalid.

In the dissenting opinion for Gillespie v. State of Oklahoma, Justice Oliver Wendell Holmes Jr. argued that the majority's decision to uphold a state law banning out-of-state newspapers from publishing liquor advertisements violated First Amendment rights and was inconsistent with previous Supreme Court rulings on similar issues. He contended that states should not have the power to regulate what citizens can read or learn about through publications from other states, as this infringes upon their constitutional right to free speech and press. Furthermore, he believed it was unreasonable for a state to impose its own moral standards onto another by restricting access to information about legal activities in those jurisdictions. In his view, such censorship could lead down a slippery slope towards more extensive limitations on freedom of expression.