Thirteen Men Freed Under the First Step Act Face Going Back to Prison

20 August 2026

Legal Battles & Legislative Updates

Thirteen Men Freed Under the First Step Act Face Going Back to Prison

Matthew Charles knows what it is like to walk out of prison and then be ordered back in.

Charles served 22 years for crack cocaine offenses, under mandatory minimums that no longer exist. In 2018 he became the first person released under the First Step Act, the bipartisan law President Donald Trump signed that December. He went back to prison once anyway, after a court reversed that first release, and then got out again. He later joined Trump at the State of the Union as a guest.

Now he is warning that 13 other men are about to be pushed through the same door in the wrong direction.

Those 13 were released through compassionate release, the process that lets a judge cut a sentence short for “extraordinary and compelling” reasons. The reason in these cases was usually the same. Before 2018, federal law stacked mandatory minimums for certain gun offenses, so one conviction could pile on decades of added time. The First Step Act ended that stacking for new cases. Someone sentenced under the old rules can therefore be serving far longer than the same crime would draw today. In the cases the Supreme Court took up, one man’s mandatory minimum would have been 14 years shorter and another’s 21 years shorter had they been sentenced now.

In May the Court closed that door. In Rutherford v. United States, decided with a companion case, the justices ruled that this kind of sentence disparity cannot support compassionate release, because that would make the First Step Act retroactive when Congress meant it to apply only going forward. Justice Sonia Sotomayor dissented, writing that the majority “conjured” limits that neither Congress nor the Sentencing Commission imposed. The same day, in Fernandez v. United States, the Court held that doubt about a conviction’s integrity cannot justify compassionate release either, over a dissent from Justice Ketanji Brown Jackson.

The ruling does not just shape future cases. It pulls the legal ground out from under people who are already free. Charles names two of them. Clifford Darden was recently elected a deacon at his church. Damian Smith was freed after 16 and a half years of a 42-year sentence and now volunteers for his congregation. Their releases rest on the same reasoning Rutherford rejected.

Charles now advocates for Families Against Mandatory Minimums, or FAMM. His argument is blunt. These men did the work. Judges looked at their records and let them out. The only tool left, he writes, is the president’s clemency power. For 13 people who rebuilt their lives, a commutation is the difference between staying home and returning to a cell to finish a sentence measured in decades.

More is coming. The Court will hear another First Step Act case, Maxwell v. Dinis, next term, on how early a prisoner can move to a halfway house or home confinement. Rep. Jamie Raskin filed an amicus brief in that case in August.