Ahead by a Century: Tim Edgar, Machine-Learning, and the Future of Anti-Avoidance

Tim Edgar's contributions to our understanding of tax avoidance and anti-avoidance remain ahead of their time. In this paper, the author argues that Edgar's work on building better general anti-avoidance rules (GAARs) was particularly prescient—correct in its claim that tax avoidance can and should be eliminated through effective anti-avoidance measures. The author maintains that although Edgar's position and vision will eventually be realized, Edgar himself did not anticipate the manner in which this would occur. The author's first claim is that the law is incomplete, and this incompleteness problematizes any insistence on the immediate adoption of strict anti-avoidance measures. The author explains how and why the current stage of legal development falls significantly short of completely specifying the law, including the tax law. The author's second claim is that the next decades will bring considerably more sophisticated and effective approaches to legal development. Described, in broad terms, are some of the mechanisms through which our tax systems are moving toward a legal singularity (a state of the law that is functionally complete and well specified). The author proceeds to outline the implications of his two main claims for the future of GAARs and anti-avoidance—specifically, how the realization of a much more complete system of law will leave effectively no further scope for tax avoidance. Tax law, in the asymptotic realization of Edgar's work and vision, will become well targeted and well equipped to address tax avoidance. Tax avoidance as we know it will cease to exist.