As used in this article, the concept of a "constitutional road map" refers to the practice of having the U.S. Supreme Court, when it strikes down the law at issue, suggest legislative alternatives consistent with the U.S. Constitution. In the City of Chicago v. Morales (1999), the U.S. Supreme Court held that Chicago's gang-loitering law violated due process. Despite agreeing that the gang-loitering ordinance was unconstitutional, Justice Sandra Day O'Connor suggested that Chicago had lawful alternatives at its disposal. Her concurrence then sketched out potential statutory provisions that would survive judicial scrutiny, offering a constitutional road map for legislators to follow in re-enacting the ordinance. In Dickerson v. United States (2000), the Court addressed for the first time a 32-year-old Federal law purporting to overrule Miranda v. Arizona and its consequences for custodial interrogation. In this case, the Court struck down the statute without offering encouragement, let alone guidance, for any political response. Part I of this article details the background of Chicago's gang-loitering ordinance, the noteworthy aspects of "Morales," the law's re-enactment pursuant to the O'Connor road map, and the likely court challenges to the new ordinance. Part II describes the Court's seminal decision on custodial interrogation, Congress' attempt to abrogate "Miranda" by statute, the intervening three decades of relative desuetude, the invalidation of the Federal confession law in "Dickerson," and the improbability of congressional re-enactment in its wake. Part III considers leading dialog theories, their limited application to the criminal process, and the prospects of road mapping as an alternative judicial technique. Part IV presents the likely arguments for and against constitutional road maps and offers a framework for analyzing the propriety of this judicial strategy in specific disputes. This framework is applied to Supreme Court cases, particularly "Morales" and "Dickerson." 554 footnotes