In Grosso v. United States (1967), the Supreme Court ruled that a defendant could not be charged with tax evasion for failing to pay taxes on illegally obtained income if they would have had to incriminate themselves in order to report that income. Joseph Grosso was convicted of tax evasion after he failed to pay federal excise and wagering taxes on his earnings from illegal gambling operations. He appealed, arguing that forcing him to file these returns violated his Fifth Amendment right against self-incrimination because it required him to disclose the source of his illegal income. The Supreme Court agreed, holding in a 5-4 decision that requiring someone "to do more than 'record, compute and pay over'" their taxes constituted an unconstitutional act of compelled self-incrimination under the Fifth Amendment.

In the dissenting opinion for Grosso v. United States, Justice Harlan argued that the majority's decision to overturn Grosso's conviction was incorrect. He believed that there were no grounds for invoking the Fifth Amendment privilege against self-incrimination in this case because it did not involve a "real and appreciable" risk of incrimination. Furthermore, he contended that even if such a risk existed, it should have been raised at trial rather than on appeal. The justice also disagreed with the majority’s interpretation of Marchetti v. United States (a related case), arguing instead that Marchetti only protected individuals from being compelled to provide information directly used in criminal prosecutions against them - something he felt wasn't applicable here as Grosso had voluntarily provided his gambling records during an investigation into tax evasion.