Whether the dividend-equivalent and tax-reimbursement payments were deductible as expenses paid or incurred in carrying on Du Pont's trade or business under § 23(a) of the Revenue Act of 1928.
Holding
No. Even assuming that Du Pont's investment activities constituted a trade or business, the payments did not proximately result from that business and were not ordinary expenses of it.
Reasoning
The Court treated the taxpayer's claimed business status as an assumption rather than deciding whether managing and conserving a large personal estate is itself a trade or business. Deductions are matters of legislative grace, not general equitable fairness, and § 23(a) permits only expenses that bear the required connection to the taxpayer's own business.
The liability originated in the du Pont Company's effort to improve its management by enabling key executives to acquire company stock. Du Pont supplied the shares because the company believed it could not legally make the sale itself. Thus, the payments flowed proximately from the corporation's business purpose, not from Du Pont's separate activity of managing his investments.
A stockholder cannot convert a corporation's business into his own merely because the transaction may protect or increase the value of his investment. Under Burnet v. Clark and related decisions, expenditures undertaken to assist or preserve a corporation do not become deductible business expenses of its shareholder. The replacement stock loan arranged in 1929 did not change that result, because the origin of the liability—not the later form of financing—controls.
The payments also failed the independent requirement that an expense be ordinary. “Ordinary” means normal, usual, or customary in the particular business at issue. An expense can be ordinary even if it occurs only once for a taxpayer, but the transaction generating it must be common or frequent in that line of activity.
The record did not show that Du Pont was in the business of securities trading, where short-sale carrying charges might be customary. Nor did it show that investors engaged in conserving and enhancing their estates ordinarily borrow stock or finance employee stock-purchase arrangements for corporations in which they hold shares. These unusual payments were therefore unlike routine investment-management costs such as investment advice, clerical assistance, or safe-deposit-box rent.
The payments may have been necessary in the practical sense that they enabled Du Pont to complete an arrangement beneficial to his estate. But necessity alone does not satisfy § 23(a); Congress required an expense to be both necessary and ordinary.