In Boykin v. Alabama (1968), the U.S. Supreme Court overturned the conviction of an African American man, Edward Boykin Jr., who had pleaded guilty to five charges of robbery in an Alabama court without being fully informed of his rights or understanding the consequences of his plea. The Supreme Court ruled that a defendant's guilty plea is not valid unless it is made voluntarily and intelligently, with full awareness of its implications and potential penalties. This decision emphasized that courts must ensure defendants understand their constitutional rights before accepting a guilty plea, including their right to trial by jury, protection against self-incrimination and right to confront one’s accusers.

In the dissenting opinion for Boykin v. Alabama, Justice Harlan argued that the majority's decision to overturn a guilty plea due to lack of explicit record of waiver of rights was unnecessary and impractical. He contended that it is not always feasible or necessary for courts to obtain an explicit on-the-record waiver from defendants before accepting their pleas. Instead, he believed that if a defendant voluntarily pleads guilty with competent counsel present, this should be sufficient evidence that they are aware of their rights and have chosen to waive them. Furthermore, Harlan expressed concern about the potential impact on lower courts which would now need to ensure every right is explicitly waived on record during plea bargains - a process he deemed as burdensome and potentially disruptive in court proceedings.