This chapter examines reparation as a central factor in the Second Chances Framework, highlighting how emotions shape decisions about whether wrongdoers deserve another opportunity. Unethical behavior in organizations often provokes anger, shock, resentment, and disappointment, and while some argue these emotions should be bracketed out in favor of rational principles, they also reveal underlying values of fairness, trust, and responsibility. Ignoring them risks shallow or ineffective decision-making. The chapter explores this in depth through the case of Iceland’s 2008 financial collapse, where senior bankers faced prosecution for fraud, market manipulation, and breach of trust. Despite public outrage and legal consequences, the bankers denied wrongdoing and offered no reparative action. They have instead claimed to have been made into scapegoats by the authorities. Public opinion remains divided: some welcome their economic contributions, while others distrust their integrity. Reparation thus proves crucial in balancing precedent, trust, transparency, and fairness when navigating the ethics of second chances.