In Rubin v. United States, the Supreme Court ruled on a case involving federal tax law and its application to charitable donations of art. The Rubins, who were art collectors, donated several pieces to museums and claimed substantial deductions on their income taxes based on appraisals of the artwork's value. However, the Internal Revenue Service (IRS) disputed these valuations and assessed deficiencies against them for three taxable years: 1965, 1966, and 1967. The Tax Court sided with the IRS after finding that some of the appraisals had been inflated. The Rubins appealed this decision all the way up to Supreme Court arguing that they should not be penalized because they relied in good faith upon professional advice when claiming their deductions; however,the court rejected this argument stating it was irrelevant whether taxpayers acted in good faith or relied upon professional advice if those deductions were found excessive. The ruling affirmed that taxpayers bear an objective burden of proving their entitlements under tax laws regardless of subjective beliefs about what is permissible.

In the dissenting opinion for Rubin v. United States, Justice Brennan disagreed with the majority's interpretation of Section 331(a) of Title 21, arguing that it was too broad and could potentially criminalize innocent mistakes made by food producers. He pointed out that under this interpretation, even a minor deviation from FDA regulations - such as an incorrect font size on a label - could be considered a crime. Justice Brennan argued that Congress did not intend to make every violation of FDA regulations a criminal act when they passed the Federal Food, Drug and Cosmetic Act in 1938. Instead, he believed they intended to target only those who intentionally deceive consumers or put them at risk through their actions. Therefore, he felt that the Court should have interpreted Section 331(a) more narrowly to avoid unjustly punishing food producers for simple errors.