Learned Hand's Contribution to the Law of Tax Avoidance

Abstract

The extent to which taxpayers are free to minimize their tax obligations by choosing one legal form rather than another as the vehicle for a transaction or relationship has preoccupied lawyers and administrators since the inception of the federal income tax. There is a common awareness among practitioners that different legal procedures will often lead to different tax consequences, although in economic terms the end results are essentially the same. In selecting the form in which a proposed business transaction shall be cast, therefore, it is said to be vital for the tax planner to consider and evaluate "all of the possible routes to his client's destination," and the ability to generate a multiplicity of formal alternatives, however sterile the exercise in any other context, is usually thought to be the true mark of a creative tax adviser. But one hastens to add that the planning job does not end there. The Internal Revenue Service does not regard itself in every case as bound by the taxpayer's choice of form, so that a plan which is "jigsaw cut" to the letter of the law may nevertheless be challenged by the government for one reason or another. Hence the ability to perceive alternatives in great number can sometimes be a dangerous intelligence unless it is combined with a power to forecast the likely reaction of the Service and the courts to each of the alternatives in view.