In Whipple v. Commissioner of Internal Revenue, the Supreme Court ruled in 1962 that a taxpayer who loans money to corporations he controls cannot deduct losses on those loans as business bad debts. The court held that these were nonbusiness bad debts because they did not create a significant and bona fide involvement in the corporation's operations beyond that of an investor or creditor. In this case, Fred B. Whipple had created and controlled several corporations for which he provided funding through both equity investments and loans. When some of these businesses failed, Mr.Whipple claimed deductions for his losses on the unpaid loans as business bad debts under section 23(k)(4) of the Internal Revenue Code (1939). However, IRS disallowed them arguing they were nonbusiness bad debts deductible only as short-term capital losses under section 23(k)(4). The Tax Court sided with IRS but was reversed by Sixth Circuit Appeals Court leading to Supreme Court review where it sided with IRS stating such transactions are more akin to an investor protecting their investment rather than regular course of trade or business thus not eligible for full ordinary loss deduction.

In the dissenting opinion for Whipple v. Commissioner of Internal Revenue, it was argued that the majority's decision to deny Mr. Whipple's claim for business deductions was incorrect and inconsistent with previous rulings by the Court. The dissent emphasized that Mr. Whipple had made substantial loans to his corporations over a period of many years, actively participated in their management, and ultimately suffered significant financial losses when they failed - all activities consistent with those of a typical businessman or investor engaged in trade or business activity as defined under tax law. Therefore, he should be entitled to deduct these losses from his taxable income just like any other businessman would be able to do so under similar circumstances.