When the government wants to impose exceptionally harsh punishment on a criminal defendant, one of the ways it accomplishes this goal is to divide the defendant’s single course of conduct into multiple offenses that give rise to multiple punishments. The Supreme Court has rendered the Double Jeopardy Clause, the Cruel and Unusual Punishments Clause, and the rule of lenity incapable of handling this problem by emptying them of substantive content and transforming them into mere instruments for effectuation of legislative will.

This Article demonstrates that all three doctrines originally reflected a substantive legal preference for life and liberty, and a systemic bias against overpunishment. A punishment was deemed excessive under the Cruel and Unusual Punishments Clause if it was greater than an offender’s retributive desert, as measured against longstanding punishment practice. Prior to the twentieth century, if prosecutors proposed a novel unit of prosecution for a given crime, judges asked two questions: (1) Does this unit of prosecution give the government the opportunity to bring multiple charges based on a single course of conduct?; and (2) If so, would the bringing of multiple charges create an arbitrary relationship between the offender’s culpability and his cumulative punishment, measured in light of prior punishment practice? If the answer to both questions was yes, judges would declare the punishment invalid under the Cruel and Unusual Punishments Clause, the Double Jeopardy Clause, or the rule of strict construction of penal statutes (the forerunner to today’s rule of lenity). By recovering this methodology for addressing prosecutorial efforts to divide crime and multiply punishments, we can ameliorate our current mass incarceration crisis and make the American criminal justice system more just.