In a series of decisions issued during his last two years on the bench, Judge Jack B. Weinstein of the Eastern District of New York set out a new vision for the imposition and termination of federal supervised release. Specifically, beginning with his decision in U.S. v. Trotter in 2018, he focused on imposing shorter terms, terminating supervised release early, and vowed not to return people to prison for supervised release violations caused by habitual alcohol or marijuana use. This article examines Judge Weinstein’s jurisprudence on supervised release and looks at the impact of his new vision. After reviewing Judge Weinstein’s pre-Trotter supervised release cases, it examines the Trotter case and his subsequent supervised release decisions. The article concludes by reviewing the impact of these decisions on the imposition of supervised release in the Eastern District as well as the wider federal criminal legal system.

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