Arkansas carried out a double execution Monday night, marking the first time in nearly 17 years that any state has killed two people on the same day. At 7:20 p.m. local time, 52-year-old Jack Harold Jones was pronounced dead in the death chamber at the Cummins Unit state prison. Infirmary workers had spent more than 45 minutes unsuccessfully trying to put a central line into his neck. According to a court filing, during Jones’s execution, he was “moving his lips and gulping for air,” which suggests he continued to be conscious during the lethal injection. The controversial sedative midazolam is administered as part of a cocktail of execution drugs to make prisoners unconscious, but it’s repeatedly failed to do so during other executions, leading to painful deaths. Ahead of Monday night, Jones’s lawyers had argued his medical condition was likely to reduce the sedative’s effectiveness, leading to an unconstitutionally painful death, but this argument was rejected by a court. Before being killed, Jones gave a long final statement, in which he apologized to the daughter of Mary Phillips. Jones has admitted to raping and killing Mary Phillips in 1995. His final words were “I’m sorry.” Lawyers for the second man, Marcel Williams, filed a last-minute appeal for a stay of execution following Jones’s killing, arguing Williams could also experience a botched, painful death. A district court judge initially granted a temporary stay of Williams’s execution but then allowed the execution to go forward. Williams was pronounced dead at 10:33 p.m. He had been convicted and sentenced to death for the 1994 kidnap, rape and murder of Stacy Errickson. Monday night’s executions came after legal challenges reached the U.S. Supreme Court, which rejected a stay for Williams. The only justice to dissent in this ruling was Justice Sonia Sotomayor. The last double execution carried out in the United States was in 2000 in Texas. Arkansas carried out its first execution in 16 years on Thursday, killing Ledell Lee, and plans to execute a fourth man, Kenneth Williams, this coming Thursday. The state had initially planned to execute eight people within 11 days this month—an unprecedented rate of executions in modern U.S. history. We’ll have more on Arkansas’s executions later in the broadcast with Guardian reporter Ed Pilkington.