In Deutch v. United States, the Supreme Court was asked to consider whether a taxpayer could deduct legal expenses incurred in defending against criminal charges related to his business activities. The petitioner, Mr. Deutch, had been indicted on several counts of tax evasion and conspiracy for actions taken as part of his role as president and principal stockholder of a corporation. He sought to deduct over $200k in legal fees from his gross income on the grounds that they were ordinary and necessary business expenses under section 23(a)(1)(A) of the Internal Revenue Code. The court ruled against him by affirming the decision made by lower courts that these costs were not deductible because they arose from personal misconduct rather than normal corporate operations or transactions. It held that allowing such deductions would be contrary to public policy since it would effectively subsidize unlawful activities with taxpayers' money.

In the dissenting opinion for Deutch v. United States, Justice Whittaker argued that the majority's decision to uphold Deutch's conviction was based on a misinterpretation of Section 145(b) of the Internal Revenue Code. He contended that this section should be read as criminalizing only willful attempts to evade or defeat tax payment, not mere failures to pay taxes due. In his view, there was insufficient evidence presented at trial to prove beyond reasonable doubt that Deutch had acted with specific intent to evade or defeat his tax liability; rather it seemed he simply failed in paying them due financial difficulties and other personal reasons. Therefore, he believed the conviction should have been reversed and remanded for retrial under proper instructions regarding what constitutes an offense under Section 145(b).