In the O'Neil v. Vermont case of 1891, John O'Neil was convicted for selling liquor without a license in violation of state law and received multiple fines for each sale he made, resulting in an overall fine that exceeded his ability to pay. The U.S Supreme Court upheld the conviction and sentence despite arguments from O’Neil's lawyers who claimed that this punishment violated the Eighth Amendment’s prohibition against cruel and unusual punishments. However, Justice Field dissented arguing that while each individual fine might be constitutional, their cumulative effect could constitute as cruel and unusual punishment if they were grossly disproportionate to the offense committed. This dissenting opinion laid groundwork for future cases involving proportionality under the Eighth Amendment.

In the dissenting opinion for O'Neil v. Vermont, Justice John Marshall Harlan argued that the punishment imposed on O'Neil was cruel and unusual, thus violating the Eighth Amendment of the Constitution. He contended that a fine of $6,300 and imprisonment for 19,914 days (approximately 54 years) for selling liquor without a license was grossly disproportionate to the offense committed. Harlan believed this case raised questions about whether state laws could infrive upon individual rights protected by federal law. He also questioned if it were possible to impose cumulative punishments for what is essentially one act or transaction - in this case multiple sales from one barrel of whiskey being treated as separate offenses each with its own penalty. His view did not prevail at that time but would later influence future rulings regarding proportionality in sentencing.