When Anti-avoidance Measures and Property Rights Collide

This article explores when anti-avoidance provisions in (national) tax legislation violate the right to property. While the intersection of tax law and human rights gains increasing attention in global discussions on tax fairness, effective enforcement, and legal safeguards for taxpayers, the question of whether anti-avoidance measures infringe upon property rights remains underexplored in academic literature. Drawing on the European Court of Human Rights’ method of examination, alongside analyses of recent cases from the Dutch and American Supreme Courts, the article argues that certain anti-avoidance rules—particularly those reclassifying income, such as the Danish provision taxing all shareholder loans as dividends upfront—may impose disproportionate burdens on taxpayers. <br/><br/>Building on these insights, the article introduces an analytical framework comprising five indicators to systematically identify tax avoidance measures that risk violating property rights. Through rigorous examination of both national and international jurisprudence, this study contributes to the evolving debate on reconciling the demands of effective tax administration with the imperative of safeguarding fundamental rights. The findings offer critical guidance for tax practitioners, policymakers, and authorities for identifying existing tax-avoidance measures and/or designing future ones that ensure robust and efficient tax compliance while aligning with constitutional and human rights standards.