This paper examines Shakespeare’s History of Henry the Fourth (1 Henry IV) in the light of Prince Hal’s prodigal narrative of “investment” and “reformation” displaying the salient feature of early capitalist reconception of “loss” as potential profit. The etymology of the word “invest,” which is now commonly understood in the economic sense, originates from the word “vest,” i.e. “to clothe.” In Shakespeare’s period, it meant to vest a person with a position or power, in other words, to appoint a person of a certain political office. Hal’s prodigal narrative leading toward his succession of the crown involves this political economy of “invest” derived from the expansion of the word: from its initial political usage to incorporate economic meaning, as in “to invest” money for future profit. This paper especially reconsiders Prince Hal’s political prudence to perform “prodigality” and his reckless adventure against his double Hotspur as a form of “investment”, an act of risk-taking despite the future uncertainty. I aim to contextualize the meaning and the process of prince Hal’s narrative of “stray and return” in the literary history of prodigals, ultimately to demonstrate that the prodigal prince’s audacious ethos of risk-taking venture is inextricably linked to post-Reformation skepticism.