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Trump Is Their Best Hope to Avoid Going Back to Prison
After more than 16 years, a judge granted Damian Smith’s petition for “compassionate release.” (All photos by Jacob Langston for The Free Press)
A Supreme Court ruling in May created a nightmare scenario for about a dozen former inmates, who will likely be locked up again unless the president intervenes.
By P.G. Sittenfeld
08.19.26 — U.S. Politics
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Damian Smith couldn’t believe it when his lawyer told him last summer that he would be freed from federal prison after 16 and a half years, less than halfway through a 42-year sentence for two armed robberies he participated in as a teenager.

A judge had granted Smith’s petition for “compassionate release,” a process that gives inmates the possibility of a shorter sentence or freedom in “extraordinary and compelling” circumstances. In the past, compassionate release offered little more than false hope; the vast majority of prisoners’ requests never made it to court—and those that did were usually rejected by a judge.

That changed in 2018 after President Donald Trump signed the First Step Act, widely regarded as the most significant criminal justice reform in a generation. Among its many provisions, the law eliminated the use of “stacking”—that is, stringing together mandatory maximum sentences together consecutively—for firearm possession during a violent crime. As a result, someone convicted today of exactly what put Smith behind bars in 2009 would receive a sentence less than half as long as his.

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P.G. Sittenfeld
P.G. Sittenfeld is a contributor to The Free Press, and his recent work has also been published in The New York Times, The Washington Post, Esquire, Slate, Outside, The Hill, America Magazine, and Princeton Alumni Weekly. His journey has taken him from Princeton University to politics to prison to successful Supreme Court petitioner. He regularly speaks around the country at law schools and law firms, in private sector settings, and in American prisons. He enjoys writing about the U.S. legal and criminal justice system, faith, and fatherhood, and he lives with his wife and three young sons in Cincinnati.
Tags:
Donald Trump
Crime
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