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TERRE HAUTE, Ind. – Brandon Bernard became the ninth federal prisoner put to death under the Trump administration, as he was executed by lethal injection on Thursday night.

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Bernard, 40, was executed at the U.S. Penitentiary in Terre Haute, Indiana. He was pronounced dead at 9:27 p.m ET.

Bernard directed his last words to the family of the couple he killed, The Associated Press reported. “I’m sorry,” he said. “That’s the only words that I can say that completely capture how I feel now and how I felt that day.”

The U.S. Supreme Court denied the stay of execution at about 8:30 p.m. ET. Three of the Supreme Court justices dissented in the decision.

Earlier Thursday evening, the U.S. Court of Appeals for the District of Columbia Circuit, voted 5-4 to deny a stay of execution.

Bernard’s execution is one of five the federal government hopes to carry out before President Donald Trump leaves office on Jan. 20, The Washington Post reported. Federal executions during a presidential transfer of power are rare, according to the AP. The last time executions occurred during a lame-duck period was during the presidency of Grover Cleveland in the 1890s.

Another execution is scheduled for Friday. Alfred Bourgeois, 56, is scheduled to die in the penitentiary in Terre Haute, the Texas Tribune reported. Bourgeois was convicted of killing his 2-year-old daughter in 2002 at the Corpus Christi Naval Air Station, the newspaper reported.

In the cases of Bernard and Bourgeois, the killings were classified as federal crimes because they occurred on military property, the Tribune reported.

Bernard was 18 when he and his co-defendant, Christopher Andre Vialva, then 19, were convicted of murder for their roles in the killing of Todd and Stacie Bagley, two youth ministers from Killeen, Texas, according to the AP.

On June 21, 1999, Todd Bagley was asked for a ride by the defendants. After he agreed, they put the couple into the car’s trunk and drove them to an isolated area on the Fort Hood, Texas, military reservation, according to court records.

Bernard was not the architect of the robbery plan that led to the deaths of the Bagleys, the Indianapolis Star reported.

Vialva was executed by lethal injection on Sept. 24, becoming the first Black federal prisoner executed this year. According to court records, Vialva shot both of the victims in the head, according to court records. Bernard lit their vehicle on fire while the Bagleys were still inside it. An autopsy revealed that Todd Bagley was killed by a gunshot wound, but Stacie Bagley’s cause of death was smoke inhalation, the Star reported.

>> Inmate becomes first Black executed in federal prison this year

Bernard’s case drew high-profile condemnation, the Post reported. Kim Kardashian West, among others, tweeted about Bernard’s case and shared a petition calling for his death sentence to be commuted to life in prison, the newspaper reported.

Defense attorneys argued in court and in a petition for clemency from Trump that Bernard was a low-ranking, subservient member of the group, the AP reported. They say both Bagleys were likely dead before Bernard doused their car with lighter fluid and set it on fire, a claim that conflicts with government testimony at trial.

“I can’t imagine how they feel about losing their family,” Bernard said about surviving Bagley relatives in a 2016 video statement from death row. “I wish that we could all go back and change it.” He also described taking part in youth outreach programs and embracing religion, saying, “I have tried to be a better person since that day.”

The federal executions, which began in July, were the first in the U.S. since 2003.