PurposeIn Portugal, between 1989 and 2010, capital gains from corporate shares were exempted, while gains from other instruments, like limited liability companies (LLC) equity stakes, were taxed. Inevitably, this non-neutral tax treatment originated a notorious tax arbitrage, consisting in the transformation of the legal status of a LLC into a corporation, the subsequent share sale and tax exemption. In tax litigation, many arbitration rulings were delivered, with widely divergent decisions. The purpose of this paper, using a blend of the legal research method and case analysis, is to discuss three research questions. Should the general anti-abuse clause (GAAC) be applied to this tax planning operation? Why the divergence in arbitration rulings? Is this anomalous arbitration outcome because of the wording the GAAC and its complexity or, contrarily, does it emerge from the disconnection between the set of rules governing capital gains taxation and the legislative intent that is behind such rules?Design/methodology/approachThe methodology used in this paper is based on a mix of the legal research method and case analysis. In the case of legal research, a hermeneutic approach – meaning that documents, texts and their interpretation can produce important fruits to the development of the field – is a tested and fruitful approach. Besides being a hermeneutic discipline, it is an argumentative one. By exposing arguments that confirm or deny particular solutions, legal research (e.g. in criminal, business or administrative law) can influence better legislative choices by political actors. Advantages of case analysis include lessons learned from observation. The author discusses if the application of the GAAC to an arrangement that originated a tax exemption can be validated by the usual interpretative lines that doctrine sustains should be observed when a GAAC is used to void legal schemes. The pros and cons of tax arbitration are also highlighted.FindingsThe conclusion of this paper is that the GAAC is not the crux of the problem. Instead, a contradictory or, at least, disconnected relation between the expressed intent of legislators and the wording of capital gains tax clauses is, in our view, the main reason for such divergent arbitration rulings on the same issue.Practical implicationsThe author believes that the paper is a contribution to the literature, given the global use of anti-abuse clauses and the interpretative complexities they originate. Moreover, the analysis in this paper is carried out in a legal setting where a disconnection is detectable between the expressed legislative intent and the legal drafting of personal income tax rules related to the exemption of capital gains. Studying the complexity added by this feature of the Portuguese legislation serves as a reminder of the importance of careful and well-crafted wording to achieve consistent court outcomes.Originality/valueThe paper has value to governments, tax authorities and tax managers, given the ever-increasing use of anti-abuse clauses in many countries, and the potential use of arbitration in similar settings.
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