In the case of Leonard Portuondo, Superintendent, Fishkill Correctional Facility v. Ray Agard (1999), the U.S. Supreme Court ruled in favor of Portuondo, reversing a decision by the Second Circuit Court of Appeals that had granted habeas corpus relief to Agard. The issue at hand was whether or not it is permissible for prosecutors to comment on a defendant's opportunity to hear all other witnesses testify and tailor their own testimony accordingly during trial - an act known as "tailoring". In this particular case, Agard had been convicted for rape and murder in New York state court; his conviction was upheld by appellate courts but later challenged in federal court on grounds that such comments violated his constitutional rights under the Fifth Amendment (right against self-incrimination) and Sixth Amendment (right to confront one’s accusers). However, Justice Scalia delivered the opinion of 7-2 majority stating that these comments do not violate any specific right protected by Constitution since they are based upon courtroom realities rather than being speculative or prejudicial.

In the case of Leonard Portuondo v. Ray Agard, Justice Stevens expressed a dissenting opinion. He argued that the prosecutor's comments during trial about Agard's decision to remain silent until his court appearance violated his constitutional rights under the Fifth and Fourteenth Amendments. The justice emphasized that these amendments protect an accused person from being compelled to testify against themselves in any criminal case, which includes not having their silence used as evidence of guilt. Furthermore, he pointed out that it is common for innocent people to seek legal counsel before making statements regarding serious charges brought against them; thus implying guilt based on this action was inappropriate and misleading for jurors who may not understand its implications fully.