This article examines four major Financial Fair Play (FFP) cases that have come before the Court of Arbitration for Sport (CAS). Although significant previous work has addressed FFP in European football, there is a major gap where its treatment at the CAS is concerned. In addition to creating substantial holes in the effectiveness of FFP regulations, the progression of the four cases discussed have let some of FFP’s most egregious offenders avoid sanctions they would consider damaging. In considering two especially important cases, this article argues that Paris Saint-Germain and Manchester City have provided ample guidance for transforming mediocre clubs through disguised equity infusions to circumvent FFP until a sustainable revenue structure is created. For the CAS, the case line resulting in major FFP offending clubs escaping meaningful sanctions builds upon a body of anti-doping jurisprudence that has had the effect of shifting the cost-benefit analysis of rule breaking. This failure in both the FFP and CAS realms leads into a larger emergent policy reform conversation.