There are complex legal and ethical tradeoffs involved in using intensified regulation to bring smoking prevalence to near-zero levels. The authors explore these tradeoffs through a lens of health justice, paying particular attention to the potential impact on vulnerable populations. The ethical tradeoffs explored include the charge that heavy regulation is paternalistic; the potentially regressive impact of heavily taxing a product consumed disproportionately by the poor; the simple loss of enjoyment to heavily addicted smokers; the health risks posed by, for example, regulating nicotine content in cigarettes--where doing so leads to increased consumption. Turning to legalistic concerns, the authors explore whether endgame strategies constitute a form of 'regulatory taking'; whether endgame strategies can be squared with global trade/investment laws; whether free speech rights are infringed by aggressive restrictions on the advertisement and marketing of cigarettes.