Remorse is a profound and complicated emotion and it is one that is evaluated in a surprising number of legal contexts. One particularly high-stakes evaluation of remorse occurs in the context of discretionary parole, when a parole board is deciding whether to release an inmate back to the community. This Article explains the arguments justifying the evaluation of remorse in parole hearings, evaluates how remorse is directly and indirectly incorporated into a typical parole hearing, presents legal and psychological research about the effect that the presence or absence of remorse may have on parole commissioners’ judgment of inmates’ culpability and eligibility for release, and articulates the challenges that arise in assessing remorse. Finally, this Article makes recommendations for state parole boards that wish either to eliminate remorse as a consideration in parole hearings or assess it more consistently.

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