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Frictions And Tax-Motivated Hedging: An Empirical Exploration Of Publicly-Traded Exchangeable Securities, William M. Gentry, David M. Schizer Jan 2003

Frictions And Tax-Motivated Hedging: An Empirical Exploration Of Publicly-Traded Exchangeable Securities, William M. Gentry, David M. Schizer

Faculty Scholarship

As financial engineering becomes more sophisticated, taxing income from capital becomes increasingly difficult. We offer the first empirical study of a high profile strategy known as "tax-free hedging," which offers economic benefits of a sale without triggering tax. We explore nontax costs that taxpayers face when hedging by issuing so-called "DECS," "PHONES," and other publicly-traded exchangeable securities. Focusing on 61 transactions between 1993 and 2001, we shed light on why taxpayers might prefer to hedge through private "over-the-counter" transactions: An offering of exchangeable securities is announced in advance and implemented all at once, triggering an almost 5 percent decline in ...


Taxation Of Preferred Stock In Corporate Reorganizations, Bruce E. Gagnon Dec 1969

Taxation Of Preferred Stock In Corporate Reorganizations, Bruce E. Gagnon

Vanderbilt Law Review

Among the sections added to the revised version of the Internal Revenue Code of 1954 was section 306, designed to close a gaping loophole which might have permitted many taxpayers to withdraw earnings and profits from a corporation through the distribution and sale of preferred stock and to receive capital gains treatment at the shareholder level rather than the dividend treatment ordinarily applicable to such distributions. In this article, Professor Gagnon argues that, as applied to corporate reorganizations, section 306 falls far from its mark. After discussing the purpose and operation of section 306 and related sections, the author suggests ...


Income Tax--Capital Gains Tax--Meaning Of "More Than 80 Percent In Value Of The Outstanding Stock" Under Section 1239, Michigan Law Review Jan 1968

Income Tax--Capital Gains Tax--Meaning Of "More Than 80 Percent In Value Of The Outstanding Stock" Under Section 1239, Michigan Law Review

Michigan Law Review

The sale of property by a taxpayer to a corporation which he controls has been a frequently attempted method of tax reduction for more than thirty years. Such a transaction has the advantage of maintaining ownership of the property in virtually the same hands, while at the same time resulting in a substantial mitigation of tax liability. For instance, in the post-World War II period, when property values were generally increasing, a taxpayer could sell to his controlled corporation at a gain depreciable property with a basis lowered by adjustments for prior depreciation allowances. The gain was immediately taxable at ...