ST. LOUIS (AP) — A man convicted of fatally shooting an eastern Missouri couple has had his death penalty overturned for a third time.

The St. Louis Post-Dispatch reports that U.S. District Judge Catherine Perry called the portion of the trial that led up to Carman Deck’s latest death sentence “fundamentally unfair.” She ordered him to serve life in prison without parole for the killings of James and Zelma Long during a 1996 robbery of their home near De Soto.

She wrote Thursday that jurors were prevented from “adequately considering compassionate or mitigating factors that might have warranted mercy.” It was unclear whether the state would appeal.

Two other death sentences also were overturned, including by the U.S. Supreme Court in 2005 because he had been shackled in the presence of jurors.