After a stay was denied by the U.S. Supreme Court, the Department of Justice moved forward and put Brandon Bernard to death for a murder he was convicted of two decades ago. It was the ninth federal execution of 2020 and one that comes as the Trump administration’s days come to a close.

Bernard’s lawyers called the execution a “stain on America’s criminal justice system.”

Bernard, 40, was pronounced dead by lethal injection at 9:27 p.m. Thursday (Dec.10) night at the federal prison at Terre Haute, Ind. The execution was performed despite several last ditch efforts from his lawyers, criminal justice advocates and even the prosecutor and jurors involved in his case who said that there was exculpatory evidence that should have changed his sentence from death to life in prison.

“Tonight, those of us who love Brandon Bernard—and we are many—are full of righteous anger and deep sadness at the actions of the federal government in taking his life. Brandon’s life mattered,” his attorney, Robert Owen, said in a statement to Newsweek.

RELATED: Brandon Bernard Set To Be Executed In Federal Prison Despite Push From Advocates To Change His Sentence

Several advocates, including Kim Kardashian West attempted to convince Trump to delay or cancel the execution, but he never responded to them. In a Nov. 18 editorial published in the Indianapolis Star, federal prosecutor Angela Moore said several factors should have prevented him from being subject to capital punishment including race, the development of the brain in adolescence, and his ability to mature.

“Through time and experience, I have come to appreciate that a teenager who takes part in committing a terrible crime may transform over the years into a thoughtful adult,” Moore wrote. “From everything I have read, it appears that Brandon is just such a person – someone who, even in prison, has maintained rich relationships with his loved ones and worked to find meaning in his life by helping at-risk teenagers avoid a criminal path.”

Bernard, who was 18 at the time of his crime, was convicted of the 1999 killing of two youth ministers from Iowa, Todd and Stacie Bagley. They had stopped at a convenience store to use a payphone in Killeen, Tex., after visiting friends and attending a church meeting. Bernard and his co-defendant Christopher Vialva, who was 19, planned to rob them, prosecutors argued. The couple offered to give Bernard and Vialva a ride but instead they held the couple at gunpoint and put them in the trunk of their vehicle, CBS News reported.

Court records show when the vehicle got to Fort Hood, Vialva shot both victims in the head and Bernard set their vehicle on fire. Because the killings took place on military grounds, it became a federal case. Prosecutors said that Stacie Bagley was still alive when the car was ignited and died from smoke inhalation, so they requested the death penalty. However, Bernard was not the ring leader in the group and was only recruited to participate by Vialva. He never fired a weapon and set the car on fire to destroy the vehicle, not to kill anyone. This evidence was further cited by his lawyers in an attempt to delay the execution.

However, the Supreme Court did not accept the argument and allowed the federal Bureau of Prisons to put him to death.

“Today, the Court allows the Federal Government to execute Brandon Bernard, despite Bernard’s troubling allegations that the Government secured his death sentence by withholding exculpatory evidence and knowingly eliciting false testimony against him,” wrote Justice Sonia Sotomayor in her dissent. “Bernard has never had the opportunity to test the merits of those claims in court. Now he never will.”

Vialva was executed Sept. 24, also at Terre Haute. The three other assailants connected to the case have also been convicted. Two have been released and the other will remain in prison until 2030.

Thursday’s execution was reportedly the first in 130 years to be carried out during a presidential lame duck period. Also, CNN reports Bernard is the youngest person to be sentenced to death in 70 years for a crime he committed as a teenager.

In his last words, he issued an apology to the victims’ families. “I’m sorry … I wish I could take it all back, but I can’t,” Bernard said in his three-minute statement. “That’s the only words that I can say that completely capture how I feel now and how I felt that day.”

Bernard was one of five federal prisoners, all are Black and male except for one white woman, set to be executed by the Justice Department in the final few weeks of the Trump administration. The next, Alfred Bourgeois, a 56-year-old Black truck driver convicted of killing his daughter, is scheduled for Friday (Dec. 11).