Both ancient Roman and contemporary American tort law recognize a type of damages that, instead of compensating the plaintiff for harm suffered, punishes the wrongdoer. In American law, courts can award two distinct amounts of money: compensatory damages for the plaintiff’s loss, and punitive damages as punishment and deterrence. Ancient Roman law had more extreme forms of remedies. In both legal systems there has been a trend to restrict punitive damages over time. The United States made efforts in the 1980s to place caps on punitive damages, which were referred to as “relics of the past,” and enhance requirements for awarding them. Do these efforts in both systems to restrict punitive damages mean that legal systems tend to provide harsher and stricter remedies in their earlier stages? And that they abolish these remedies in favor of mere compensation when the systems reach more “civilized” stages? If the answer to these questions is yes, then a conclusion might be drawn that, because the ancient Roman and contemporary American law societies are so different from one another, then this movement away from harsher remedies must also be true in all cultures. This paper analyzes the history of punitive damages in both ancient Roman and contemporary American tort law in order to answer these questions.