In this article, the author explores the evolution of the Court of Justice of the European Union’s approach to cross-border loss relief, focusing on the influence of the ability-to-pay principle and broader political and economic factors. Using the landmark Marks & Spencer case as a starting point, the article analyses subsequent jurisprudence and evaluates whether legal reasoning or contextual pressures shaped the outcomes. Ultimately, it examines how the Court navigated the tension between EU integration and national tax autonomy — a legal journey marked by sharp turns, second guesses and doctrines that, once promising, now seem to echo from another era.