In the case of Richardson, as Treasurer of Porto Rico, v. Fajardo Sugar Company in 1915, the U.S. Supreme Court ruled on a dispute over taxes levied by Puerto Rico's government against the Fajardo Sugar Company. The company argued that these taxes were unconstitutional under the Foraker Act - an act passed by Congress to establish a civilian government in Puerto Rico after its acquisition from Spain following the Spanish-American War. However, Justice Joseph McKenna delivered an opinion for a unanimous court upholding Puerto Rico's right to tax local businesses and property owners without violating any federal laws or regulations. The ruling affirmed that while Puerto Rico was subject to certain restrictions imposed by Congress through acts like Foraker Act, it still retained significant autonomy over its internal affairs including taxation policy.

In the dissenting opinion for the case of Richardson, as Treasurer of Porto Rico, v. Fajardo Sugar Company in 1915, Justice Oliver Wendell Holmes disagreed with the majority's decision that Puerto Rico could not tax federal property. He argued that when Congress gave Puerto Rico power to levy taxes in its own right and for its own purposes, it implicitly allowed taxation on all property within its jurisdiction unless specifically exempted by law. Holmes believed this included federal properties such as those owned by Fajardo Sugar Company. He contended that there was no explicit exemption from local taxation given to federally-owned lands or corporations operating under a federal charter like Fajardo Sugar Co., thus they should be subject to local taxes imposed by Puerto Rican authorities. The justice emphasized his belief in respecting Congressional intent and maintaining consistency with previous rulings which upheld state rights to tax non-exempted Federal entities within their borders.