The US Supreme Court declined Thursday to delay the execution of 40-year-old Brandon Bernard, who was subsequently pronounced dead by legal injection at the Federal Correctional Center in Terre Haute, Indiana at 9:27 PM local time. Bernard had filed an emergency request seeking a stay of execution.

Bernard was one of five adolescents convicted for a “gang-related carjacking that ended in [the] double murder” of youth ministers Stacie and Todd Bagley. The crime occurred in Fort Hood, Texas in 1999. Christopher Vialva, the apparent leader of the crime, was executed by the federal government in September. The other three co-defendants received lesser sentences.

Since his conviction, Bernard spent more than 20 years in prison. For many years, Bernard contested his sentence. According to the emergency stay, Bernard discovered that the government had been in “possession of favorable information relevant to his sentence” at the time of his trial. The government had allegedly withheld this evidence, and Bernard did not discover its existence until after the first appeal of his sentence had been denied.

Less than two hours before his scheduled execution, Bernard filed two “supplements” to his stay application, stating that two distinguished lawyers had agreed to join his legal team. The supplements asked the court to stay the execution for 14 days to give the new additions to Bernard’s legal team time to review and provide support for Bernard’s case.

However, the Supreme Court denied on Thursday the stay of execution, allowing the execution to proceed. Bernard was pronounced dead at 9:27 p.m. that same day.

Bernard’s death is the ninth federal execution that has occurred since the Trump administration lifted the moratorium on the federal death penalty. Four more federal executions are set to occur under the Trump administration prior to the upcoming inauguration of President-elect Joe Biden.