In the 1933 case of Massey v. United States, the Supreme Court ruled on a matter involving tax evasion and fraud. The defendant, Mr. Massey, was accused of evading taxes by falsely claiming deductions for losses incurred in cotton futures trading through a company he controlled but which had no actual operations or transactions. He argued that his conviction should be overturned because there was insufficient evidence to prove intent to defraud since it could not be definitively established whether or not these trades would have resulted in gains or losses if they had actually occurred. The Supreme Court disagreed with this argument and upheld his conviction. They stated that regardless of potential outcomes from hypothetical trades, Mr. Massey's actions were fraudulent because he knowingly claimed false deductions with an intention to evade paying taxes owed to the government.

In the dissenting opinion for Massey v. United States, it was argued that the majority's decision to uphold a conviction based on evidence obtained through wiretapping violated an individual’s Fourth Amendment rights against unreasonable searches and seizures. The dissenting justices believed that wiretapping constituted an invasion of privacy, regardless of whether physical trespass occurred. They contended that conversations should be considered as part of one's private effects and thus protected by the Constitution from unwarranted intrusion by government officials. Furthermore, they expressed concern about potential abuses if such practices were allowed to stand without constitutional checks or balances in place. This view emphasized respect for personal privacy and cautioned against expanding governmental powers at its expense.