In Lafler v. Cooper and Missouri v. Frye, the Supreme Court held that given the prevalence of plea bargaining in the modern American criminal justice system, the plea negotiation phase of a criminal trial is a “critical stage” of the proceedings. Thus, since a defendant has a Sixth Amendment right to counsel at all critical stages, and thus during plea bargaining, he also has the corollary right to the effective assistance of counsel during plea bargaining. Going forward, courts will be required to address claims that counsel’s failure to persuade a client to accept an offer that was clearly in the client’s best interests was ineffective assistance. This issue will be especially salient in capital cases given that approximately half of current death row inmates rejected a plea bargain that would have spared their lives. In most of the cases in which capital defendants refused to plead guilty in exchange for a life sentece, the prosecution’s offer represented not only the most likely trial outcome, but – in many cases – the best possible trial outcome. This article discusses the reasons defendants facing the death penalty reject life-sparing offers and trial counsel’s responsibilities in encouraging a client to accept a plea bargain in cases literally involving life and death.