Judge Jack B. Weinstein approached every sentencing with his trademark compassion and intellectual rigor. This was nowhere more evident than in two of the most challenging sentencing contexts: child pornography and terrorism. This essay considers Judge Weinstein’s refusal to sentence based on assumptions about defendants and their conduct, and his insistence on empirical data, expert evaluations, and asking the hardest questions about motivation and future behavior before imposing sentence. It focuses on Judge Weinstein’s sentencing practices in terrorism and child pornography cases, the two areas in which Congress and the U.S. Sentencing Commission have most limited judicial discretion in sentencing. It shows that despite those limits, Judge Weinstein sought always to impose individualized sentences based on the actual person before him. He believed every person—no matter their worst act—could be salvaged, and deserved happiness.

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