In Nalle v. Oyster, the U.S. Supreme Court ruled on a dispute over taxation and property rights in Washington D.C. Charles E. Nalle, who owned bonds secured by real estate mortgages in the District of Columbia, argued that his bonds were being unfairly taxed by George E. Oyster Jr., an assessor for the Board of Personal Tax Appraisers for Washington D.C.'s tax department. The court had to decide whether these types of bonds could be considered taxable personal property under local law or if they should be exempt from taxation as securities issued under authority of Congress. The Supreme Court sided with Nalle, ruling that his mortgage-backed securities were not subject to local taxation because they fell within exemptions granted by federal statute (35 Statute at Large 571). This decision clarified how certain financial instruments are treated under tax law and underscored the supremacy of federal laws when there is conflict between state/local and national legislation.

In the dissenting opinion for Nalle v. Oyster, Justice Holmes disagreed with the majority's decision to uphold a tax assessment on shares of stock owned by a resident in Washington D.C., but issued by corporations outside of D.C. He argued that this was an unconstitutional imposition on interstate commerce and violated due process rights under the Fifth Amendment. According to Holmes, taxation should be based on where property is located rather than where its owner resides; therefore, stocks should only be taxed in their state of issuance. He also contended that it was unfair for shareholders to bear the burden of corporate taxes indirectly through diminished dividends and directly through personal property taxes imposed upon them because they resided within D.C.'s jurisdiction.