In the case of Donnelley v. United States in 1927, the Supreme Court ruled on a matter involving tax evasion and fraud. The defendant, Donnelley, was accused of evading taxes by falsely claiming deductions for bad debts from his business that were not actually incurred. He argued that he should be acquitted because there was no specific law at the time making it illegal to claim false deductions on a tax return. However, the court disagreed with this argument and upheld his conviction for defrauding the government under general federal laws against fraud. They reasoned that even though there wasn't a specific statute addressing false claims on tax returns when he committed his actions, such conduct still constituted fraudulent behavior punishable under existing laws.

In the dissenting opinion for Donnelley v. United States, Justice Oliver Wendell Holmes Jr., joined by Justice Louis Brandeis, argued that the defendant's conviction should be overturned because his actions did not constitute a crime under federal law. They contended that while Donnelly may have acted dishonestly in his business dealings, he did not commit mail fraud as defined by statute since there was no evidence of him having defrauded anyone through use of the postal service. The justices believed that interpreting the mail fraud statute to include such broad and vague concepts as "dishonesty" or "unfairness" would make it overly expansive and potentially unconstitutional. They warned against stretching criminal statutes beyond their clear intent to punish behavior which lawmakers had not explicitly deemed illegal.