In the 1900 case of McDonald v. Massachusetts, the U.S. Supreme Court upheld a decision by the state's highest court to convict and sentence William McDonald for larceny after having been previously convicted of three separate crimes in New York and Massachusetts. The defendant argued that his constitutional rights were violated because he was not present when evidence about his previous convictions was presented to the jury, nor did he have an opportunity to cross-examine witnesses regarding these prior offenses. However, the Supreme Court ruled that there had been no violation of due process or equal protection under Fourteenth Amendment since it is within a state’s power to inflict harsher penalties on habitual criminals than those who are first-time offenders.

In the dissenting opinion for McDonald v. Massachusetts, Justice Harlan argued that the defendant's constitutional rights were violated by his second trial and subsequent conviction for a crime he had already been acquitted of in a previous trial. He contended that this was double jeopardy, which is explicitly prohibited by the Fifth Amendment to the Constitution. Harlan also disagreed with the majority's interpretation of state law, arguing that it did not allow for retrial after acquittal in such cases as McDonald's. Furthermore, he expressed concern about potential abuses of power if prosecutors could simply retry defendants until they achieved their desired outcome - an infringement on individual liberties and due process rights under both federal and state constitutions.