Montgomery v. Louisiana arrived at the Supreme Court at the intersection of three conceptually challenging and jurisprudentially opaque areas of law. First, Montgomery came to the Court as an Eighth Amendment case requiring the Justices to struggle yet again with the counter-majoritarian question of what limits the Cruel and Unusual Punishments Clause puts on government powers to impose certain sentences on certain defendants for certain crimes. Second, Montgomery came to the Court as a retroactivity case requiring the Justices to struggle with the practical question of how new constitutional rules are to apply to old and seemingly settled criminal judgments. Third, Montgomery became a federalism case because the Justices, when granting certiorari review, added the jurisdictional question of whether the Court even had authority to review how Louisiana had implemented the Supreme Court’s prior decisions on Eighth Amendment and retroactivity issues.In this short essay, I briefly discuss the doctrinal puzzles of Montgomery in each of these three areas of law --- Eighth Amendment limits on sentences, retroactivity of new constitutional rules, and federal review of state criminal adjudications. Specifically, I explain how the Montgomery opinion achieved a messy trifecta: through one relatively short opinion, the Supreme Court managed to make each of these areas of law significantly more conceptually challenging and jurisprudentially opaque than they already were.
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