Gray v. C. I. R., s. 75-1041

• Citation: 561 F.2d 753
• Decision Date: 21 September 1977
• Docket Number: Nos. 75-1041,s. 75-1041
• Parties: 77-2 USTC P 9685 John D. GRAY and Elizabeth N. Gray, John R. Gray, First National Bank of Oregon, Guardian, Joan E. Gray, First National Bank of Oregon, Guardian, Janet L. Gray, First National Bank of Oregon, Guardian, Laurie J. Gray, First National Bank of Oregon, Guardian, Anne L. Gray, First National Bank of Oregon, Guardian, Petitioners-Appellants, v. COMMISSIONER OF INTERNAL REVENUE, Respondent-Appellee. to 75-1046.
• Court: United States Courts of Appeals. United States Court of Appeals (9th Circuit)

Page 753

561 F.2d 753

77-2 USTC P 9685

John D. GRAY and Elizabeth N. Gray, John R. Gray, First

National Bank of Oregon, Guardian, Joan E. Gray, First

National Bank of Oregon, Guardian, Janet L. Gray, First

National Bank of Oregon, Guardian, Laurie J. Gray, First

National Bank of Oregon, Guardian, Anne L. Gray, First

National Bank of Oregon, Guardian, Petitioners-Appellants, v. COMMISSIONER OF INTERNAL REVENUE, Respondent-Appellee.

Nos. 75-1041 to 75-1046.

United States Court of Appeals, Ninth Circuit.

Sept. 21, 1977.

Michael Waris, Jr., Washington, D. C., argued, for petitioners-appellants.

Stephen M. Gelber, Atty., Tax Div., U. S. Dept. of Justice, Washington, D. C., argued, for respondent-appellee.

Appeals from Decisions of the United States Tax Court.

Before GOODWIN and SNEED, Circuit Judges, and BLUMENFELD, ^* District Judge.

SNEED, Circuit Judge:

Taxpayers appeal from a decision of the Tax Court holding that what in form was a sale of taxpayers' stock in a wholly owned corporation was in substance a liquidation of the corporation. John D. Gray, 56 T.C. 1032 (1971). The case demonstrates anew the need to elevate substance over form in interpreting a sophisticated code of tax laws where slight differences in a transaction's design can lead to widely divergent tax results. It also demonstrates, however, the difficulties in determining the substance of a transaction when dealing with complex business arrangements in which the items of commerce frequently are legal abstractions such as corporate entities and shares.

The present transaction has at least five plausible characterizations, all with substantially different tax results. According to their theory, taxpayers sold their shares in a wholly owned corporation, containing only cash and preferred stock in another of taxpayers' corporations, to an unrelated party in an arm's-length transaction; the preferred stock was then redeemed from the corporation after the sale was completed and, thus, after taxpayers' control over the redeeming corporation could no longer be attributed to the sold corporation through section 318 of the Internal Revenue Code (hereinafter Code). ¹ The Tax Court, however, focusing on the purported sale, held that taxpayers had in substance liquidated the corporation following which the preferred stock was redeemed directly from the hands of the taxpayers. We take a third position. We accept the sale format in which taxpayers chose to cast their transaction. At the same time, however, we believe that the redemption of the preferred occurred before rather than after the sale was effectuated.

I.

THE FACTS.

In 1960, taxpayers John D. Gray and family were the principal shareholders of two corporations profitably engaged in the manufacture and sale of saw chains both here and abroad. Domestic operations were centered in Omark Industries Inc. (hereinafter Omark), of whose stock all but about 10 percent was held by taxpayers. Foreign sales were handled by Omark Industries (1959), Ltd. (hereinafter Omark 1959), a Canadian corporation owned entirely by taxpayers. In an effort both to prepare Omark for an eventual public offering and to avoid disputes with the minority shareholders of Omark, taxpayers in late 1960 decided to realign the Omark-Omark 1959 relationship into that of parent-subsidiary. This was accomplished by Omark forming a Canadian subsidiary, Omark Industries (1960) Ltd. (hereinafter Omark 1960), and having the subsidiary acquire the assets of Omark 1959 and assume its liabilities. Omark 1959 in exchange received $10,000 in cash, a $82,604 line of credit, and 15,000 shares of Omark 1960 $100-par, non-cumulative preferred. The name of Omark 1959 was then changed to Yarg, Ltd. (hereinafter Yarg). ²

Following the acquisition of Yarg's assets by Omark 1960, taxpayers attempted to convert Yarg into a real estate investment corporation. Gray actively investigated a variety of real estate investments during 1961 and 1962. Gray's efforts to find suitable investments, however, were unsuccessful. While Yarg did make a series of investments in Oregon corporations, no real estate was ever purchased.

By 1962, several factors had convinced taxpayers to terminate their ownership of Yarg as expeditiously as possible. Because of the failure to find satisfactory real estate investments for Yarg, the IRS was likely to classify Yarg as a foreign personal holding company subject to sections 551 et seq. of the Code. ³ Under the foreign personal holding company provisions, taxpayers would be taxed at ordinary income rates on any undistributed investment earnings of Yarg. ⁴ To make matters worse, legislation had been introduced into Congress which, if passed, would tax as dividend income any gain recognized on the liquidation of a controlled foreign corporation such as Yarg. ⁵

Taxpayers considered a variety of means for terminating their interest in Yarg including transferring their stock in Yarg to Omark in exchange for Omark stock in a nontaxable section 351 transaction, contributing the Yarg stock to a capital exchange fund, and liquidating Yarg. Each of those alternatives, however, had distinct disadvantages and taxpayers ultimately decided to sell their stock in Yarg to an outside buyer. Although two investment banking firms were commissioned to find a buyer, it was Gray's attorney who ultimately located a purchaser. Frank H. Cameron (hereinafter Cameron), a Canadian businessman, offered to purchase the Yarg stock for "net book value less 41/2 percent of undistributed income"; he insisted, however, that prior to purchase, all of Yarg's assets be reduced to cash and Yarg's liabilities be reduced to only capital and surplus.

At this point, Yarg's assets consisted of a small amount of cash, minor investments in three Oregon corporations, and the 15,000 shares of Omark 1960 preferred. In line with the all-cash requirement in Cameron's offer, Gray purchased Yarg's Oregon investments at book value in cash. However, taxpayers balked at reducing the Omark 1960 preferred to cash prior to the sale. Cameron's insistence on cash was understandable. There was no guarantee that the Omark 1960 preferred would be redeemed in the near future. And, while the book value and redemption price of the Omark 1960 preferred was $1,500,000, its fair market value was considerably less, taxpayers once in the course of this litigation having stipulated a value of only $1,000,000. From taxpayers' standpoint, however, a redemption of the Omark 1960 preferred prior to the sale of the Yarg stock would lead to foreign personal holding company income, taxable to Gray and his family as ordinary income. ⁶ Ultimately, it was agreed between the parties that Cameron would purchase the Yarg stock while Yarg still held the Omark 1960 preferred, but that the purchase would be subject to a condition subsequent negating the transaction if the Omark 1960 preferred was not redeemed within six days after the purchase. Cameron would be free to waive the condition subsequent if he wished. To ensure that Omark 1960 would be able to redeem the preferred shares, Gray arranged for Omark and another Omark subsidiary to lend approximately $1.3 million to Omark 1960 four days prior to the planned sale.

On September 21, 1962, Cameron, acting through two wholly owned Canadian corporations, gave two certified checks totalling $1,681,400 to personal representatives of taxpayers in exchange for all the outstanding Yarg stock. The checks, the Yarg stock, the Yarg corporate records and the Omark 1960 preferred stock, all properly endorsed, were then placed in escrow with the Bank of Montreal. By the terms of the escrow, the Bank was to return the checks to Cameron and the other excrow items to taxpayers if the Omark 1960 preferred had not been redeemed by September 26, 1962 and Cameron had not waived the condition. On September 22, with Cameron and two associates purportedly installed as Yarg's new directors, Yarg requested that Omark 1960 redeem its preferred stock; the request was made by means of a letter previously drafted by Gray's Canadian attorney. The stock was redeemed on September 25, 1962, and the escrow was closed.

Taxpayers treated the 1962 transaction as a sale of the Yarg stock, reporting their profit on the transaction as capital gains. The Commissioner assessed deficiencies against taxpayers contending that the transaction was in reality a constructive dividend to taxpayers of the assets of Yarg followed by a second constructive dividend on the redemption of the Omark 1960 preferred; both dividends would be taxable at ordinary income rates. ⁷ The Tax Court held that both characterizations were wrong. According to the Tax Court, the 1962 dealings constituted a constructive liquidation of Yarg on September 21 followed by a redemption of the Omark 1960 stock from the hands of taxpayers on September 25.

II.

ANALYSIS.

We agree with the Tax Court that the taxpayers' characterization of the transaction must be rejected. We believe that the controlling issues are when and from whom the redemption was made, however, and not whether the taxpayers liquidated or sold their stock.

Assuming that taxpayers are correct in characterizing their transaction as a sale rather than a liquidation, the facts indicate that the substance of the sale followed rather than preceded the redemption of the 1960 preferred. The fact that the agreement was cast in the form of a sale subject to condition subsequent, which may be considered a completed sale under Canadian law, is irrelevant for purposes of federal taxation. We must look to the relevant concepts of federal tax law to determine when the sale occurred. Commissioner v. Tower, 327 U.S. 280, 287-88, 66 S.Ct. 532, 90 L.Ed. 670 (1946); Hudspeth v. United States, 471 F.2d 275, 277 (8th Cir. 1972); Estate of Starr v. Commissioner, 274 F.2d 294, 294-95 (9th Cir. 1959). For tax purposes, sale is essentially an economic rather than a formal concept. Our...