The second execution Monday night was briefly delayed by a federal judge so she could consider claims that the first lethal injection may have been botched, but she lifted that stay shortly before 9:30 p.m. local time. The second inmate was pronounced dead about an hour later, according to the Associated Press, which had a reporter witness it.

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These lethal injections marked the first back-to-back executions in the United States since Texas carried out two death sentences in one night nearly two decades ago. Arkansas was also the first state to make such an attempt since a widely publicized botch in Oklahoma in 2014.

Arkansas hoped this month to resume executions by carrying out eight death sentences in 11 days, an unprecedented schedule that has been thwarted by court orders blocking half of those lethal injections. Even after some lethal injections were stayed, officials shifted their focus to carrying out the remaining executions on the schedule.

Jack H. Jones Jr. and Marcel W. Williams, both of whom were on Arkansas death row since being convicted of brutal murders two decades ago, unsuccessfully sought to delay their lethal injections set for Monday night at a state prison southeast of Little Rock.

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Both appealed to the U.S. Supreme Court, which rejected their requests Monday afternoon and evening. Jones was executed first. Williams was scheduled to follow not long after, but his lethal injection was postponed while his lawyers argued in federal court that Jones’s execution was botched, something state officials denied. Both men had said they had medical issues that could complicate the executions, which involve injections of three drugs.

The Supreme Court first denied Jones’s request for a stay about an hour before the executions were set to begin at 7 p.m. Monday in Arkansas. Justice Samuel A. Alito Jr., who is assigned cases from the federal circuit covering Arkansas, referred the request to the full court, which denied it without explanation; Justice Sonia Sotomayor was the only member of the court to register a dissent.

Jones was pronounced dead at 7:20 p.m., 14 minutes after his lethal injection got underway, according to the Associated Press, which had a reporter serve as a media witness. He delivered a last statement expressing remorse.

Williams’s appeal was still pending when Jones’s execution ended, but not long after, the justices denied the stay request. Again, no explanation was given and Sotomayor was the only justice to note a dissent.

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While the Supreme Court’s decision to reject Williams’s requests seemingly meant that the second execution could proceed as planned, it was pushed further into the night after a federal judge issued a temporary stay.

U.S. District Judge Kristine Baker issued the order indefinitely delaying Williams’s execution after his attorneys filed a motion asked for a stay, arguing that Jones’s “execution appeared to be torturous and inhumane.” Baker later issued an order denying the request and lifting her stay after a hearing was held.

In the motion, Williams’s attorneys, noting that he shared medical issues with Jones, said corrections staff struggled to insert a central line into Jones’s neck. The attorneys said that corrections officials did not wait five minutes, as required by the execution policy, after the injection began to check and make sure Jones was unconscious after the sedative was administered. They also alleged that Jones was still “moving his lips and gulping for air” after five minutes had elapsed.

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One media witness says Jones’s “lips did move, but only very briefly at the very start of the process.” According to the Associated Press, its reporter who witnessed Jones’s execution said that the inmate moved his lips briefly after the sedative was first administered and noted that officials put a tongue depressor in his mouth intermittently during the first few minutes. The AP reporter also said Jones’s chest stopped moving two minutes after they checked his consciousness.

Under the Arkansas lethal-injection protocol, state officials must check to make sure inmates are unconscious at least five minutes after the sedative is injected. If they remain conscious, officials are then directed to inject a second dose of the sedative.

Williams’s attorneys say in their filing that he did not agree to have a central line inserted, and warned that their client’s execution could be “even more torturous” than Jones’s.

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State officials filed a short response pushing back on these assertions about the IV and the execution, calling them “inaccurate” and “utterly baseless.”

“The claim that Jones was moving his lips and gulping for air is unsupported by press accounts or the accounts of other witnesses,” the Arkansas response stated. “The drugs were administered to Jones at 7:06 p.m. and he was pronounced dead at 7:20 p.m. There was no constitutional violation in Jones’ execution.”

After Baker lifted her stay, Williams’s execution proceeded, and he was pronounced dead at 10:33 p.m. after a 17-minute lethal injection, the Associated Press reported.

Williams is the ninth inmate executed in the United States so far this year. With three executions in four days, Arkansas has carried out a third of the lethal injections nationwide in 2017.

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Gov. Asa Hutchinson (R), who scheduled the lethal injections and did not issue a statement following the execution last week, issued statements late Monday saying that “the rule of law was upheld” and “justice has prevailed.”

In a statement after Jones’s execution, Hutchinson said that the “victim’s family has waited patiently for justice” for two decades. After Williams’s execution, Hutchinson thanked the victim’s family for their patience and said “in this case our laws ended in justice.”

The lethal injections in Arkansas were planned as part of a schedule that would have been without parallel in modern capital punishment. Hutchinson set eight executions to occur in pairs — back-to-back on four nights spread out over this week and last — and while most executions occur with little public notice, the timetable in Arkansas drew unusual attention and some criticism.

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Attorneys for the inmates filed a volley of appeals seeking to delay the executions, while two dozen former corrections officials wrote a letter to Hutchinson asking him to reconsider the schedule. They warned that the schedule was “needlessly exacerbating the strain and stress placed on” the people carrying it out and saying the timetable could “increase the chance of an error occurring.”

Arkansas officials defended this schedule as necessary because their stock of midazolam, a common sedative that has provoked controversy after some executions and is one of three products used in the state’s executions, expires at the end of April. Due to an ongoing shortage of lethal injection drugs, Arkansas authorities say they are not sure if more can be obtained. Leslie Rutledge (R), the state’s attorney general, pledged to fight attempts to delay the remaining executions, saying that “families have waited far too long to see justice.”

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Death-row inmates in Arkansas also appealed to the U.S. Supreme Court as a group, but those requests have been rebuffed, most recently Monday, when the high court denied a request to rehear a case from Arkansas inmates that the justices had already denied. No explanations were given, though Justice Sotomayor said she would have granted the petitions in that case.

The lethal injections on Monday come just four days after Arkansas resumed executions, carrying out the death sentence for Ledell Lee after the Supreme Court declined stay requests.

Last week, the Arkansas Supreme Court blocked the first two executions on the schedule, and another execution planned for the same night as Lee’s was stayed. Another execution is planned for Thursday night, while a second originally set that night was stayed this month by a federal judge.

While two executions per night had been the original plan in Arkansas, Jones and Williams appear to be the only two inmates who will actually be put to death on the same night this month.

Jones, 52, was sentenced to death in 1996 for raping and killing Mary Phillips. According to court records, Jones stalked and killed Phillips, a bookkeeper, and before killing her, he beat her 11-year-old daughter so severely that police thought she was dead when they got to the scene.

Jones’s attorneys have argued in court that he has medical conditions that could result in the Arkansas execution method causing him severe pain, according to court records. In a filing, his attorneys said Jones has diabetes, hypertension and several other conditions that cause him to be on medication that could bring intense or painful suffering because of a possible tolerance to the sedative used in the lethal injection.

State officials argue that Jones’s challenge involves “guesswork” about the sedative and “is no different than the many lethal-injection challenges” he has filed before. Baker, the federal judge, denied that motion Friday, saying Jones’s case did not show “a significant possibility” that the lethal injection process could cause that pain and suffering.

After Jones was executed, Rutledge, the attorney general, released a statement saying she hoped this helped Phillips’s family.

“This evening, Lacey Phillips Manor and Darla Phillips Jones have seen justice for the brutal rape and murder of their mother, Mary Phillips,” Rutledge said in a statement. After detailing the case, Rutledge added: “The Phillips family has waited far too long to see justice carried out, and I pray they find peace tonight.”

Williams, 46, was sentenced to death in 1997 for abducting, robbing, raping and killing Stacy Errickson, who was 22 and was living at the Little Rock Air Force Base while her husband was serving overseas. Arkansas officials, in court filings opposing a stay in his case, said he forced her at gunpoint to take cash from ATMs before raping, beating and strangling her.

Attorneys for Williams have argued in court filings that he had poor counsel during his trial in both his guilt and penalty phases, which they said meant he was sentenced to death despite the jury not hearing any mitigating evidence arguing against the death penalty.

In another filing, they pointed to health issues, saying he weighs 400 pounds and suffers from several medical maladies that meant the planned lethal injection “was more likely to maim than kill him.” His attorneys argued for stays on both counts, but the U.S. Court of Appeals for the 8th Circuit rejected both requests on Friday.

Rutledge said she felt the execution provided justice for Errickson’s family and friends.

“I hope that tonight’s lawful execution brings much-needed peace to all of Stacy’s loved ones, particularly her now-adult children Brittany and Bryan,” she said in a statement.

The Arkansas Supreme Court rejected stay requests from both men. The 8th Circuit, which had denied an appeal filed by the eight inmates facing execution that challenged the Arkansas method of execution, also denied another challenge Friday that was filed by some of the inmates — including Williams, but not Jones — and focused on the state’s clemency procedures.

The double execution was the country’s first since August 2000. Texas was in the midst of carrying out 40 death sentences that year, the most for any state in a single year since the U.S. Supreme Court reinstated the death penalty in 1976, according to the Washington-based Death Penalty Information Center. (Executions nationwide have fallen since that time, and last year, 20 death sentences were carried out nationwide.)

Before the double execution in 2000, the first inmate’s last words were an admonition against racism targeting black people, according to records kept by Texas corrections officials. He then said, “Let’s do it.” The second inmate apologized to his victim and his family before saying, “I am ready. I love you all.”

Arkansas is not the first state to plan a double execution since then. Perhaps the most highly publicized botched lethal injection in recent memory occurred the last time a state tried carrying out two executions in one night.

Officials in Oklahoma later blamed that bungled execution on a misplaced IV. In a state review, officials involved in the process said the back-to-back scheduling added to the stress they felt.

This story, first published at 4:58 p.m. on Monday, has been updated repeatedly with news from Arkansas.