The U.S. Supreme Court case People of Porto Rico v. Title Guaranty and Surety Company in 1912 revolved around a dispute over the interpretation of the Foraker Act, which established civil government in Puerto Rico after it was ceded to the United States by Spain following the Spanish-American War. The issue at hand was whether or not certain provisions within this act extended to corporations doing business on the island that were incorporated under mainland U.S law, specifically regarding taxation rules. The court ruled against Title Guaranty and Surety Company, stating that while they could operate in Puerto Rico as a foreign corporation, they were still subject to local laws including those related to taxes. This decision reinforced Puerto Rican autonomy over its internal affairs despite being an unincorporated territory of America.

In the dissenting opinion for People of Porto Rico v. Title Guaranty and Surety Company, Justice Oliver Wendell Holmes Jr. argued that Puerto Rico should be considered a territory of the United States rather than a foreign jurisdiction in relation to its ability to enforce tax laws on American corporations operating within its borders. He disagreed with the majority's view that Puerto Rico was not part of U.S., asserting instead that it had become an integral part of U.S. after being ceded by Spain following Spanish-American War in 1898. Holmes believed this status gave Puerto Rican government authority to impose taxes on American companies without violating constitutional protections against double taxation, as these protections did not apply when dealing with territories or possessions outside continental U.S.. The justice also contended that previous rulings which treated territories as foreign jurisdictions were outdated and needed reconsideration given changing political realities.