On the morning of his execution, Clayton Lockett hid under the covers.

Before a team of correctional officers came to get him at 5:06 a.m., he fashioned a noose out of his sheets. He pulled the blade out of a safety razor and made half-inch-long cuts on his arms. He swallowed a handful of pills that he’d been hoarding. And on April 29, 2014, when the team of officers knocked on the door of his cell in the Oklahoma State Penitentiary in McAlester, Oklahoma, Clayton Lockett—a 38-year-old convicted murderer—pulled a blanket over his head and refused to get up.

The officers left and asked for permission to tase him. While they were gone, Lockett tried to jam the door. They came back, forced their way in, tased him, and dragged him out.

Eleven hours later, at about 5:20 p.m., after a medical examination, X‑rays, eight hours in a holding cell, and a shower, Lockett was brought by a five-member strap-down team into the death chamber. It was a small, clinical-looking room with white walls and a polished floor that reflected the lights overhead. A gurney stood in the center of the room; above it hung a microphone for Lockett’s final words.

One of the walls in the chamber had a pair of baseball-size holes through which IV lines could pass into the chemical room, a small space where three executioners would administer the drugs that would kill him. The executioners had been driven to the prison earlier in the day, and had put on hoods as they approached. They would remain out of sight until after Lockett was dead.

There had never been a question of Lockett’s guilt. Fifteen years earlier, on June 3, 1999, he had stood in a ravine and aimed a 12-gauge shotgun at Stephanie Neiman, a 19-year-old who had graduated from high school two weeks earlier. Lockett and two accomplices had beaten one of Neiman’s friends and raped another. Lockett told Neiman multiple times that he would kill her if she didn’t promise to keep quiet. He warned her one last time, but she insisted she would go to the police.

He pulled the trigger. The shot sent her spinning to the ground. The gun jammed; he cleared it and fired at her again. Then one of Lockett’s accomplices buried Neiman alive in a shallow grave, the dirt puffing up as she struggled to breathe, and they left her to die.

Lockett was arrested three days later, a Sunday. Mark Gibson, the district attorney who would prosecute him, went to the jail that night because Lockett wanted to give a statement. Lockett smoked a cigarette and showed no remorse as he confessed. Gibson thought he saw a twinkle in the young man’s eye, as though he was relishing the attention, and came away believing that Lockett was pure evil.

In the execution chamber, Lockett was belted to the gurney. To his left, beige blinds covered the windows to the viewing area. Soon, shadows would be visible as the seats on the other side filled up. There was so much media interest in his execution that the prison had had to draw names to decide which reporters could attend.

A clock on the wall read 5:26. The execution was scheduled to begin at 6 p.m. Lockett could expect to be dead within about 45 minutes.

Clayton Lockett (Oklahoma Department of Corrections / AP)

Since the mid-1990s, when lethal injection replaced electrocution as America’s favored method of execution, states have found drug combinations that they trust to quickly and painlessly end a life. They often use three drugs. The first is an anesthetic, to render the prisoner unconscious. The second is a paralytic. The third, potassium chloride, stops the heart.

What many people don’t realize, however, is that choosing the specific drugs and doses involves as much guesswork as expertise. In many cases, the person responsible for selecting the drugs has no medical training. Sometimes that person is a lawyer—a state attorney general or an attorney for the prison. These officials base their confidence that a certain drug will work largely on the fact that it has seemed to work in the past. So naturally, they prefer not to experiment with new drugs. In recent years, however, they have been forced to do so.

The problems began at a pharmaceutical plant in Rocky Mount, North Carolina. The Food and Drug Administration discovered that some of the drugs made there were contaminated and in April 2010 sent the manufacturer, Hospira, a warning letter. Hospira stopped producing, among other drugs, a barbiturate called sodium thiopental. No other company was approved by the FDA to make sodium thiopental, which was the anesthetic of choice for almost all of the states that carried out executions. (The death penalty is legal in 32 states; 17 of them have performed an execution in the past five years.)

With sodium thiopental suddenly unavailable, states scrambled to find alternatives. In June of that year, officials in Georgia discovered a work-around: a small-time businessman in London named Mehdi Alavi, who sold wholesale drugs through a company called Dream Pharma, would ship sodium thiopental to them. Georgia bought some from him, and then Arkansas did too. With Hospira offline, Alavi had the U.S. execution market cornered. Arizona bought sodium thiopental from him in late September and used it the next month to execute a convicted murderer named Jeffrey Landrigan. California placed an order as well.

Maya Foa, an anti-death-penalty advocate based in London, saw Dream Pharma mentioned in court documents related to Landrigan’s execution and decided to pay a visit. At the company’s address, she found a small building with peeling white paint and a placard that read Elgone Driving Academy. Inside she found two desks and, in the back of the room, a single cabinet. That was it: Dream Pharma. Alavi imported execution drugs from elsewhere in Europe and shipped them to the United States, using that cupboard in a driving school as his base of operations.

Reprieve, the human-rights organization where Foa worked, wrote to the British government, arguing that supplying drugs for executions violated British law, since the death penalty is illegal in Europe. The government balked. Stopping the shipment of a drug would hamper free trade and could be harmful to patients. Foa responded that the “patient” argument was erroneous—there was no trade of sodium thiopental between the U.S. and the U.K. for medicinal purposes. It was all for executions. This time, the government agreed. England announced tighter export restrictions, which effectively banned the sale of the drug for executions. Foa then persuaded the European Commission to follow suit by amending its torture regulation. U.S. states trying to carry out the death penalty were now blocked from buying drugs not just from England, but from all of Europe.

So they looked even farther afield. In late 2010, a company in Mumbai, Kayem Pharmaceuticals, received an e-mail from the Nebraska Department of Correctional Services. Officials there wanted an anesthetic that Kayem made mostly for clients in Angola: sodium thiopental. Kayem sold Nebraska 500 vials, enough for more than 80 executions. Soon after, Foa’s boss wrote the company to explain how Nebraska planned to use its product. When South Dakota officials tried to place an order, Kayem jacked up the price 900 percent, to $20 a vial, hoping the cost would dissuade them. It didn’t. South Dakota bought 500 vials. Kayem stopped selling the drug to the U.S. immediately after that.

Nebraska also turned to a middleman named Chris Harris, who contacted another company, called Naari, that made sodium thiopental in India. When Nebraska prison officials later announced that they’d obtained sodium thiopental from Naari, the firm’s CEO was livid. He wrote to the chief justice of the Nebraska supreme court saying he’d been duped: Naari had supplied Harris with vials of the drug only because Harris had offered to get it registered for future sale in Zambia, where there is a huge need for cheap surgical drugs. The CEO wrote that Harris was “not authorised to sell the product” to Nebraska and that Naari was “deeply opposed to the use of the medicines in executions.” He demanded that the vials be returned. They were not.

In Oklahoma, with sodium thiopental increasingly difficult to get and an execution scheduled for December 2010, officials decided they could no longer avoid finding a substitute. They settled on another powerful barbiturate that was more easily available: a short-term therapy for insomnia called pentobarbital, made in the U.S. by a Copenhagen-based company called Lundbeck. According to state officials, pentobarbital was ideal “for humane euthanasia in animals.” Oklahoma used the new drug in the execution of John David Duty. It worked.

Oklahoma had found its solution just in time: the federal Drug Enforcement Administration was about to start raiding prisons. Since Hospira had been the only FDA-approved supplier of sodium thiopental, states that had imported it had done so illegally. Prisons had become, in effect, drug smugglers, and while the FDA may have been willing to look the other way, the DEA was not. In March 2011, agents seized Georgia’s supply of sodium thiopental. In April, they seized Tennessee’s, Kentucky’s, South Carolina’s, and Alabama’s.

Meanwhile, as other states followed Oklahoma’s lead and shifted to pentobarbital, pressure mounted on Lundbeck, the drug’s manufacturer, to block prisons from buying it. Reprieve issued press releases, the Danish media picked up the story, The Lancet published an open letter urging the company to stop supplying executions, and shareholders threatened to divest.

Maya Foa knew that pharmaceutical companies like Lundbeck had no interest in supplying executions—the fact that their drugs are used to kill people makes for terrible publicity. But what could Lundbeck do about it? Foa researched the American pharmaceutical industry and learned about controls that a manufacturer can put in place to restrict a drug’s distribution if, for example, new side effects come to light or the company wants to prevent off-label uses. She met with Lundbeck’s senior executives to present an idea: Why not put distribution controls on pentobarbital, and prevent middlemen from selling it to prisons?

“We can’t do that,” one of Lundbeck’s communications officers told her. But as he began to explain his objections, the CEO interrupted.

“Why not?”

The room fell silent.

Seven months after pentobarbital was first used in an execution, Lundbeck instituted distribution controls. Departments of corrections could no longer get their second-choice anesthetic.

Oklahoma's death chamber. (AP)

At 5:30, half an hour before Lockett’s execution was to begin, a young reporter named Katie Fretland rode in a prison van with other witnesses. They were taken to the death-row law library to wait. Fretland heard a low thrumming fill the halls, the sound of inmates banging on their cell doors in tribute to the condemned.

Fretland had arrived in McAlester just that day, but Oklahoma was something of a second home to her. She’d first come in 2012, a few years out of college, after landing a 14‑week temp job with the Associated Press. The AP had asked her to cover the execution of Timothy Stemple, a Tulsa man convicted of killing his wife. Fretland tried to find out where the state would get the execution drugs, but she quickly ran into a roadblock: Oklahoma had passed a law less than a year earlier that made nearly every aspect of executions a state secret, including where officials obtained the drugs.

Fretland decided to follow the money. She had a source who worked at the prison, and she asked him how the state’s Department of Corrections would pay for the drugs. He said it would use petty cash. She couldn’t believe it. Could the department do that—use an account with no public oversight to buy execution drugs? She filed a series of records requests and kept asking questions. She found petty-cash purchases of pentobarbital totaling more than $50,000.

Pentobarbital was by now no longer available from Lundbeck, but Fretland learned that compounding pharmacies were copying execution drugs and selling them to prisons. Compounding pharmacies exist to fill niche needs—for example, making a version of a drug for a patient who is allergic to an additive in the mass-market product. Part drug company, part pharmacy, they operate in a gray area with little oversight. (In April 2013, after a deadly meningitis outbreak was traced to a compounding pharmacy in Massachusetts, FDA officials announced that they had inspected about 30 compounding pharmacies and found unsanitary conditions in all but one of them.)

Fretland kept filing records requests, and accumulated reams of documents. Her AP job ended, but she couldn’t leave the story alone. She crashed with friends while continuing to interview pharmacists and former wardens, trying to put together a picture of Oklahoma’s frantic pursuit of execution drugs.

She turned up e-mails from early 2011 in which state officials discussed how they should respond to their peers in Texas, who had asked for help addressing the drug shortage. An Oklahoma assistant attorney general wrote to a colleague, “I propose we help if TX promises to take a dive in the [University of Oklahoma–University of Texas football] game for the next 4 years.” His colleague suggested that Texas should provide tickets for “Team Pentobarbital (you, me, Martha, the Warden, Mike Oakley, plus anyone else we can think of who is deserving) to the 2011 OU‑Texas game plus an on-field presentation of a commemorative plaque at halftime recognizing Oklahoma’s on-going contributions to propping up the Texas system of capital punishment.” He added, “And throw in lifetime passes for the North Dallas Tollway, Highway 121 and the Bush Turnpike. That would be a good deal.”

Fretland also learned that in some executions, the prisoner had died of an overdose of the first drug, the anesthetic, and that the executioners had then disposed of the other two drugs by injecting them into the corpse.

Georgia had used pentobarbital from an undisclosed source in a June 2011 execution, and Fretland found e-mails from the next month proving that Oklahoma officials knew that the inmate had remained conscious for longer than he was supposed to and may have experienced severe pain. But a month after that e-mail exchange, they spent $10,400 of petty cash to buy pentobarbital. They made another purchase a year later, this time spending $40,000.

In March 2014, Fretland published her findings in The Colorado Independent. She editorialized just once. “Banter about exchanging lethal injection help for football tickets and other favors,” she wrote, “raises questions about how seriously Oklahoma officials take the death penalty.”

A month later, Fretland came to McAlester to watch Clayton Lockett’s execution. A little before 6, she and the other witnesses were taken down a long hallway. She turned a corner into the viewing area, where two tiered rows of metal folding chairs faced the death chamber. Fretland took her seat along with 11 other reporters, two of Lockett’s lawyers, and an assortment of Oklahoma officials. Stephanie Neiman’s family would sit in a separate room for the victim’s relatives. Blinds covered the windows to the death chamber, so Fretland couldn’t see what was going on inside.

She sat down, and waited.

Katie Fretland (Photo by Kenneth M. Ruggiano)

About two months earlier, Mike Oakley, the general counsel for the Oklahoma Department of Corrections, had returned from vacation to find the department in a near-frenzy. Before he’d left, the department had ordered pentobarbital from a compounding pharmacy for the executions of Clayton Lockett and Charles Warner, a 46-year-old man convicted in 2003 of raping and killing his roommate’s 11-month-old baby. But compounding pharmacies had come under pressure to stop selling drugs for executions, and Oklahoma’s supplier had backed out. With the executions scheduled for March 20 and March 27, one of Oakley’s deputies began driving around the state, walking into pharmacies and asking for pentobarbital, without success.

Oakley didn’t know why the task of finding drugs for executions fell largely to him: he had no medical training. But he wanted to help his colleagues—especially the warden, whom he considered conscientious and hardworking—because he knew how much strain carrying out a death sentence put on them. He had gone into corrections, 25 years earlier, because Oklahoma was doing interesting work in mediation between victims and offenders. Now he was about to retire, and he found himself, as his swan song, developing a new execution cocktail.

Oakley had to report on his progress to Robert Patton, the director of the Oklahoma Department of Corrections, first thing in the morning and again before he went home each day. The attorney general’s office called Oakley multiple times a day, and Patton himself was getting pressure from the governor’s office.

Both the attorney general, Scott Pruitt, and Governor Mary Fallin had elections coming up, and there were rumors that a Tea Party candidate might outflank Fallin on the right. Oakley believed they were worried about looking soft on crime.

In mid-March, Pruitt had to make the embarrassing admission, as part of a brief to the state’s court of criminal appeals, that Oklahoma didn’t have all the necessary drugs, and Lockett’s and Warner’s executions had to be delayed.

Fewer and fewer medical experts were willing to advise Oakley, even unofficially. But he had professional contacts he’d met through the National Institute of Corrections, and he asked them for advice. He and members of the attorney general’s staff also looked at expert testimony related to executions in Florida.

In October 2013, Florida had used a sedative called midazolam in the execution of William Happ. Florida officials had determined that it was “the most humane and dignified way to do the procedure.” Doctors sometimes administer midazolam during anesthesia, but usually just to relax the patient, and in combination with a drug that blocks pain. In a high enough dose, it should render the patient unconscious—but some experts argue that, unlike sodium thiopental and pentobarbital, midazolam cannot produce the deep, coma-like state needed to guarantee he feels no pain.

William Happ shook his head, blinked, and opened his mouth during his execution. Witnesses had no way of knowing whether he was in pain, but he appeared to remain conscious longer than offenders given sodium thiopental or pentobarbital. Ohio used midazolam in the execution of Dennis McGuire a few months later, and witnesses reported that McGuire snorted, heaved, clenched one of his fists, and gasped for air.

Oakley asked his counterpart in Ohio about the state’s experience with midazolam. The media had exaggerated the problems, he was told. Yes, the new drug took a little longer to put a person to sleep, but it wasn’t as bad as everyone was saying. Midazolam was also relatively easy to obtain: multiple U.S. companies made it. Oakley’s wife had just had a kidney stone removed, and one of the drugs she’d been given was midazolam. Both Oakley and the attorney general’s office recommended that the state use it.

On April 23, 2014, six days before Lockett’s execution, Mike Oakley retired.

Midazolam had been used in just two other states before Clayton Lockett's execution. (AP)

April 23 would, by coincidence, prove to be a decisive day for the Oklahoma judicial system, for Clayton Lockett, and for his legal team, including Dave Autry.

Autry is a soft-spoken man of 56 with a ponytail that hangs halfway down his back. He seems to subsist on tobacco and caffeine—24-ounce mini-mart coffee cups and jumbo cans of Red Bull clutter his office. Autry had represented Lockett for 11 years, since shortly after Lockett exhausted his state appeals. He felt just about ready, after nearly 30 years, to leave the high stakes and emotional toll of death-row work to younger lawyers. Clayton Lockett would be his second-to-last death-row client.

As time winds down, a death-penalty lawyer has one goal: keep the client alive as long as possible. In October 2013, Autry’s co-counsel, Dean Sanderford, and an attorney for Charles Warner had petitioned the U.S. Supreme Court to review their cases, a last-chance effort to argue that constitutional errors had been made during trial or sentencing. They knew the Court was unlikely to review either case. They also knew from experience that as soon as the Supreme Court declined to hear the cases, Oklahoma would set execution dates. The lawyers needed a plan they could put in motion the instant the Court decided.

The simplest strategy would have been an Eighth Amendment challenge. But they couldn’t make a convincing case that the drugs Oklahoma officials planned to use would lead to cruel and unusual punishment, because the state’s secrecy law kept them from getting any information about where the drugs were coming from. In that lack of information, however, perhaps they could find an opportunity. The lawyers could argue that the secrecy law denied their clients “access to the courts” and was therefore unconstitutional. As they prepared to make this case, Oklahoma executed Michael Lee Wilson, a 38-year-old charged with beating a co-worker to death. After the pentobarbital was injected, Wilson said, “I feel my whole body burning.”

In January 2014, the U.S. Supreme Court declined to hear the cases. Lockett’s and Warner’s lawyers joined forces to challenge Oklahoma’s secrecy law, and they requested a stay of execution for the prisoners until the challenge was decided.

The case began ping-ponging around the Oklahoma justice system. A state judge in Oklahoma City, Patricia Parrish, heard the challenge but said she didn’t have the authority to grant a stay, so the legal team appealed to the Oklahoma supreme court. The supreme court transferred the stay request to the state’s court of criminal appeals; the court of criminal appeals asked for supplemental briefs.

By that point Lockett’s execution was days away. In their supplemental brief, the lawyers for Lockett and Warner argued that any of these courts had the authority to grant a stay. The government filed an opposing brief arguing that none of the courts did. But it was in this brief, down on page eight, that Attorney General Pruitt made the stunning admission that the state did not have all the drugs it needed for the executions. Two days before Lockett was scheduled to die, he and Warner got a one-month reprieve so that the state could find drugs. A minor victory. Lockett’s execution was rescheduled for April 22, Warner’s for April 29.

The same day, Katie Fretland published her bombshell article exposing disturbing details about how the state handled executions. A week later, on March 26, Judge Parrish decided the challenge to the secrecy law in Lockett and Warner’s favor. The law was indeed unconstitutional. “I do not think this is even a close call,” she said. She still believed she lacked the authority to grant a stay, but her ruling gave Lockett and Warner another chance: their lawyers could now ask the state for information about the drugs, and perhaps find the basis for a cruel-and-unusual-punishment lawsuit.

Right away, Oklahoma announced that it would appeal. Doing so put an automatic hold on Parrish’s decision. By the time the appeal was resolved, Lockett and Warner would likely be dead. 
The case began ping-ponging again. The inmates’ legal team went to the court of criminal appeals to ask for a stay, but the judges ruled that the case didn’t belong in their court. The lawyers then turned to the Oklahoma supreme court, which told the court of criminal appeals that it did, in fact, have jurisdiction. The court of criminal appeals disagreed and again denied the stay. To Autry and the other lawyers, the judges seemed to be passing the buck back and forth while Clayton Lockett and Charles Warner waited to die.

Finally, on April 21, one day before Lockett’s execution, a miracle: the Oklahoma supreme court, divided 5–4, granted a stay. The justices made clear that they intended to seriously contemplate the issues. The ruling seemed likely to put the executions off for a long time and give Lockett and Warner a chance of actually winning the case. Since the case challenged state law, Oklahoma couldn’t take it to the U.S. Supreme Court. No court in the country could overturn the ruling.

Autry called Lockett’s stepmother and drove out to Del City to give Lockett’s favorite aunt the news in person. It was an emotional evening, one of the rare moments in a death-penalty case this far along when you get to celebrate. At the prison the next morning, Lockett was moved out of the isolation unit where the condemned spend their final days, and sent back to a regular cell.

That same day, a shocking reversal: Governor Mary Fallin stepped in. She issued an executive order saying she did not recognize the Oklahoma supreme court’s authority to grant the stay. “The execution for Clayton Derrell Lockett,” she announced, “is therefore scheduled for April 29, 2014”—just one week away, and the same night as Charles Warner’s execution.

Autry had never heard of a governor doing something like that. Was it even legal? Could a governor just do away with a ruling by the state supreme court?

The next day things got even worse: a state representative filed articles of impeachment against the five justices who had voted for the stay. The Oklahoma supreme court bowed to the pressure. Two days after saying that it would need a long and proper debate in order to determine the constitutionality of the secrecy law, the court issued a decision: the law was fine. The stay was lifted.

The national media went into a frenzy. It looked as though the state’s judicial system had collapsed. “Execution Case Roils Oklahoma Courts,” The New York Times declared; other publications quoted the attorney general calling the events a “constitutional crisis.” Reporters descended on McAlester. It seemed as though everyone with even a fleeting interest in the Oklahoma justice system had come to the penitentiary. Everyone except Governor Fallin. On the night of the executions, she was headed to the Chesapeake Energy Arena, to watch Kevin Durant and the Oklahoma City Thunder in Game Five of the NBA conference quarterfinals.

Mark Gibson prosecuted Lockett. After listening to his nonchalant confession, Gibson came to believe Lockett was pure evil. (Kenneth M. Ruggiano)

At 5:27 p.m., a paramedic approached the gurney. Like the three executioners, she would remain anonymous. Before the blinds opened, she would retreat into the chemical room while a doctor and the prison’s warden stayed with Lockett in the death chamber. But first she had a job to do: prepare the drugs and medical equipment, and get an IV into Lockett. (Those who participated in the execution either did not respond to requests for interviews or could not be reached. Court records provide a detailed account of what happened.)

The paramedic later told investigators that she’d felt incredible pressure since she’d walked into the room an hour earlier. She’d never participated in an execution that used midazolam. She’d never participated in two executions in one night—not many people in the world had. And she knew the media were watching.

To make matters worse, the equipment was all wrong: the saline was packed in bags instead of syringes, the drugs were in syringes that looked smaller than she was used to, and the tubing for the IV was the wrong kind. But she tried to focus on doing her job and getting everything set up on time. She would be paid $600 for the two executions.

The paramedic stuck a needle into a vein in Lockett’s left arm. A few drops of blood moved up the catheter—“flashback.” A good sign. It meant the needle was in the vein. But she’d forgotten tape to hold the IV in place. She asked someone to bring it to her, but the IV slipped out before she could secure it. Lockett’s arm started to bleed, so she put pressure on it and tried again. This time, she didn’t get flashback. Then she tried a brachial vein, near Lockett’s biceps. No luck there.

By now, she’d tried to place an IV three times. She’d been taught that if you can’t find a vein after the third attempt, you ask someone else to step in. So she asked the doctor to help.

The doctor, Johnny Zellmer, was a last-minute substitute. (Zellmer, whose name was revealed in a lawsuit following the execution and in multiple press reports, has not denied his involvement. He did not respond to requests for comment.) He was a local family-medicine and emergency-room physician who’d participated in just one previous execution. Zellmer had arguably violated his profession’s oath to “never do harm” the moment he stepped into the death chamber. Indeed, the American Medical Association’s code of ethics states that physicians should not participate in executions, even in a supervisory capacity. But Zellmer thought his job would be limited to checking the offender for consciousness and pronouncing the time of death. He wasn’t expecting to actually do anything to Lockett.

The paramedic’s request for help put him in the position of no longer just observing the execution but actively facilitating it. She was clearly struggling, though. He scanned Lockett’s body and didn’t see any good veins. Then Lockett turned his head, and the paramedic saw a vein in his neck pop up. She pointed it out to Zellmer. “Get me a needle for the jugular,” he said.

This was an odd choice. IVs in the neck are painful, and also hard to place. On the arms and legs, you can use a tourniquet to bring the veins up. You cannot do that on the neck, because a tourniquet on the neck is effectively a noose, and while this was an execution, it was not a hanging.

As Zellmer tried to get the needle into the jugular, the paramedic stuck Lockett three more times on his right arm, failing each time.

Zellmer got the needle into Lockett’s neck and saw flashback, but then saw blood spread under the skin—he thought the needle might have gone all the way through the vein. Zellmer decided to try a subclavian line, in a vein running beneath Lockett’s collarbone. The paramedic brought him a central-venous catheterization kit, and Zellmer numbed Lockett’s chest with lidocaine. The paramedic tried two different veins on Lockett’s right foot; both attempts failed.

Zellmer kept trying to get the needle into Lockett’s subclavian vein. He finally saw a little flashback, then lost the vein and couldn’t get the needle back in. After repeatedly sticking Lockett’s chest, he decided to try the femoral vein, in Lockett’s groin. The paramedic went to get a longer needle.

As the warden, Anita Trammell, watched the doctor and the paramedic work on Lockett, she felt a sliver of pride for the inmate. He’d now been stuck with needles more than a dozen times. She knew he was in pain, but she thought he was taking it like a man. Trammell tried to make conversation to help calm him. She knew he had been a drug user. “What was your drug of choice?” she asked him.

“Ice.”

“I thought that was a white man’s drug,” she said, and he laughed.

The paramedic came back and said she had no needles longer than an inch and a quarter. That presented a problem. The femoral vein lies deeper in the body than other veins, so they would ideally use a needle at least twice that length. There were longer needles inside a second central-venous catheterization kit, like the one they’d just used on Lockett’s chest, but neither Zellmer nor the paramedic thought of it. Zellmer asked for an IO-infusion needle. IO stands for “intraosseous”—into the bone. It is, in effect, a power drill, used to bore a hole through bone and into the marrow, and therefore doesn’t require finding a vein.

The prison had no IO needle. Zellmer had only the absurdly short one-and-a-quarter-inch needle. “Well,” he told the paramedic, “we’ll just have to make it work.”

Lockett’s prison scrubs and underwear were cut away. Zellmer stuck the needle into Lockett’s femoral vein and saw flashback on the first try. Finally, after almost an hour, they had an IV.

Right away, the paramedic noticed a potential warning sign. Saline should have been flowing easily through the IV, but it flowed only when she propped up the line. Instead of starting over, though, she taped the IV in place. Two IVs are typically used to administer the drugs, but with the execution running way behind schedule, the doctor and the paramedic decided they would proceed with just one.

Warden Trammell asked Lockett whether he needed anything. “I was gonna see if I could get my mouth wiped off,” he said. She got a Kleenex and wiped it for him.

Finally, a sheet was draped over Lockett, covering him up to his chest. The execution could begin.

A diagram from an autopsy performed on Lockett. Pathologists found nothing to explain why the doctor and the paramedic had had so much trouble placing an IV. (Oklahoma Department of Public Safety / AP)

Lockett’s closest family members were about two hours away. His stepmother, LaDonna Hollins, had made the drive to the prison countless times. During her final visit, she and Lockett had sat looking at each other and crying. “I do not want you to be at the execution,” she later recalled him saying, “because I do not know the outcome. I do not think it’s gonna be very good. Because the drugs that they use have not been tested.”

Lockett knew that Michael Lee Wilson had said “I feel my whole body burning” when the state executed him earlier that year. Lockett was scared. “Do me one favor,” Hollins told him, according to an article in the German magazine Der Spiegel. “As long as you can talk on that gurney: Talk. Let the world know how they are executing people here in Oklahoma.”

After that visit, she heard that the prison had refused Lockett’s request for a last meal—chateaubriand, fried shrimp, baked potato, garlic toast, and a whole Kentucky bourbon pie—because it exceeded the $15 limit. Hollins called the prison and said she’d pay for it, or even drive the meal down herself, but she wasn’t allowed to. She didn’t think Lockett could be spared after what he’d done, but she didn’t think he should suffer anymore, either. So she did what she’d always done: try, however she could, to offer him some small comfort.

Lockett had first shown up on her doorstep in Southern California at the age of 3, crying and soaked in urine. His mother had put him on a bus all the way from Oklahoma to live with his father. There’d been no notice.

Hollins testified in court that when Lockett was a young child, she saw his half brother, who was about five years older, lying on top of him, the two boys looking strange together. Then a call from the school. Lockett was in the infirmary. He’d come in crying and complaining of pain around his anus.

Another memory: Lockett following his father, John, from room to room as he got ready for work, and then following him out of the house, into the street. Lockett in tears, certain that his father would never return.

Once, as a birthday present for his brother John Jr., the boys’ mother agreed to talk with them on the phone. Lockett waited for his turn with anticipation—he was now 4, and hadn’t heard his mother’s voice since she had put him on the bus. But she took offense when John Jr. referred to Hollins as “Mama LaDonna,” and hung up before Lockett got to talk with her.

John Sr. disciplined Lockett and his other children with everything from belts to two-by-fours. Hollins tried to protect the boy, but she wasn’t exempt from John Sr.’s violent temper either; he broke her arm twice.

John Sr. taught his children to steal—groceries sometimes, televisions other times—and punished them only for getting caught. Hollins remembers John Sr. blowing marijuana smoke up Lockett’s nose and sitting him down to watch porn when Lockett was a child. “Boy,” he said, “you need to tear that pussy up.” That’s what he told Lockett he was going to do to Hollins.

By the time Lockett was in middle school, his father and Hollins had brought him back to Oklahoma. To his eighth-grade teacher—a woman whose son, Mark Gibson, would later prosecute him—he stood out as smart and likable. Lockett brightened around small children. He babysat younger family members, liked to cook for them, and carried them around on his back. He had a girlfriend whose baby had Down syndrome, and he was the only person who could always make the little girl smile.

But he also spent a lot of time trying to act tough, and racked up charges including burglary and intimidating a witness. At 16, he was sentenced as an adult and sent to the Oklahoma State Penitentiary. With no one to protect him, he was raped almost immediately by three other inmates.

When Lockett got out, at age 20, he wanted to be feared. He wanted everyone to know that if they crossed him, they’d pay. So, a few years later, when a guy named Bobby Bornt seemed to be holding out on a $40 debt for marijuana and a tattoo, Lockett got his cousin and a friend and a shotgun and went to see him.

That same night, by terrible coincidence, Stephanie Neiman and a friend drove to Bornt’s house in Neiman’s new Chevy pickup truck, which had a Tasmanian Devil sticker and vanity plates that read Tazzz. Neiman was an only child whose parents had instilled in her a strong sense of right and wrong. She was admired by her classmates and by school administrators for her kindness and loyalty, and because of what she had overcome—she was considered “intellectually challenged” but had played saxophone in the school band and earned her diploma. Those who worked with her at the school believe she wasn’t able to understand how serious the situation was that night, or what the consequences might be.

Neiman and Bornt had known each other since they were young children; they’d been in the same YMCA day care. When the girls arrived at Bornt’s house, Lockett and the others were already there, attacking Bornt. Neiman reacted in a way that unsettled Lockett: she seemed unafraid. He told her to hand over the keys to her truck. She said no—the truck belonged to her. Lockett and his accomplices beat up Bornt, raped Neiman’s friend, and bound all three victims. Then Lockett led the group into Bornt’s and Neiman’s trucks and out of town, north into Kay County, up on the border with Kansas. The men threatened to kill the three victims if they reported the night’s crimes to the police. Bornt and Neiman’s friend swore they wouldn’t, and Lockett later let them go. But Neiman refused. Her parents had taught her to tell the truth. So when Lockett asked whether she would go to the police, she said yes.

Lockett asked her a final time. Then he raised the gun and fired.

Twenty-three minutes behind schedule, the blinds to the death chamber opened. Warden Trammell stood facing the witnesses. She asked Lockett whether he had any last words.

“No.”

“Let the execution begin.”

Just behind Lockett’s head, in the chemical room, one of the three executioners pushed the plunger on a syringe full of midazolam. The sedative went into the tubing, traveling 132 inches through the hole in the wall, into the death chamber, under the sheet, and into Clayton Lockett’s groin.

But not all of it went straight into his bloodstream. Somehow, the IV dislodged, and midazolam was pumped into Lockett’s tissue instead of his vein. Some of the drug would make its way into his bloodstream, but the smaller dose would be less effective.

Minutes passed. Lockett remained alert. He pursed his lips and blinked. He licked his lips.

To Katie Fretland, he looked confused. Several more minutes passed. Lockett turned his head and looked toward the witnesses. He looked back up. Finally, he closed his eyes.

In the chemical room, the executioners counted time on a stopwatch. Five minutes after they pushed the midazolam into the line, they flipped a switch and a light bulb went on in the death chamber, signaling that it was time to check whether Lockett was unconscious. Zellmer got up and checked Lockett. He was still conscious. The light went off.

Two minutes later, the light came on again—a signal to check Lockett a second time. The doctor blew in Lockett’s eyes, rubbed his sternum, and pinched him. This time, he determined that Lockett was unconscious.

The executioners injected a syringe full of vecuronium bromide, a paralytic, into the line. When properly administered, vecuronium bromide blocks the signals that the nervous system sends to the muscles, turning the body into a vehicle the brain no longer controls. It’s as if the wire that connects them has been severed and signals can no longer pass—including the signal that says breathe.

An incompletely sedated person under a paralytic might look serene, because his face muscles are paralyzed. But he’s suffocating: when he tries to expand his chest and draw breath, nothing happens. The Animal Welfare Act has banned the use of paralytics without anesthesia in the euthanasia of animals.

To anti-death-penalty advocates, the fact that these drugs are used in executions is revealing. If the sedative worked, why would you need to paralyze someone? They argue that the paralytic prevents us from seeing the offender’s distress, so that the procedure appears clinical and painless—even if it’s not.

One of Lockett’s executioners would later recall noticing something strange: the plunger was hard to push. He had no way of knowing that he might be injecting fluid into tissue, though, so he simply pushed harder. He heard what sounded like a moan come from the chamber.

Zellmer watched Lockett, oblivious to the fact that, under the sheet, the IV was not in place. In the chemical room, the executioners administered the third drug, potassium chloride.

At 6:36, Katie Fretland saw Lockett move.

During Lockett’s trial and his early years on death row, he showed no remorse. In his letters, he posed as a member of a far-reaching criminal network. “Im an assassin—point blank!” he wrote to one friend. “You honestly think that my boys is gone let a nigga as valuable me go to the penn forever? Fucc No!”

He was a terror, hiding homemade weapons in his cell and once throwing urine and excrement at a guard—anything he could do to show his disdain for authority. But in letters to his father, now also in prison, Lockett still yearned for a bond. He told his father about a girlfriend on the outside.

Dad I can send her to visit you, keep me informed on how you’re doing … Dad it’s a few people on my team that will be sending me money. I’m not going to be needing all that, I just really want a tube and some canteen and Im cool. Dad, I know you aint got too many people in your corner so I know you’ll need some money. Give me a few months to get my stable in order and I can start sending you some ends through my girl.

Gradually, the weight of his crime began to overwhelm him. He talked often with Autry, his lawyer, about what he’d done to Neiman’s parents, taking away their only child. A couple of years in, he tried to kill himself. After that, he took to all the prison self-improvement pastimes: reading, painting, philosophy. Autry lent him books, and Lockett became the most well-read client the attorney had ever had. Still, there was a hollowness to Lockett’s new persona, as though he had gone from posing as a gangbanger to posing as a self-educated prison sophisticate.

When the time came for a clemency hearing before the pardon-and-parole board—one of his last chances for survival—Lockett declined to show up. Instead, he gave Autry a letter to read to Neiman’s family. “It would be disingenuous of me to tell you that I woke up one day and suddenly felt remorse,” he wrote. “Or that I found some arcane bible verse that miraculously inspired me to change. The truth is not so simple as that.” He told them that for him, remorse had been slow, but debilitating. “I want you to know that if by me relinquishing my life you find solace in my death & can one day find the strength to forgive me then I am okay with this.”

Right up to the very end, Lockett pretended he actually had some control.

To Warden Trammell, it looked as though Lockett was trying to communicate something. He kicked his right leg. He began to breathe heavily. He clenched his teeth. He rolled his head. Then he tried to speak.

My God, Trammell thought. He’s coming out of this.

Lockett lurched up against the restraints. While the witnesses looked on, he started writhing as if trying to free himself, to get up off the gurney. He struggled violently, twisting his whole body.

Autry, sitting in the viewing area, couldn’t believe it; next to him, Dean Sanderford, Lockett’s other lawyer, began to cry. Lockett got his whole head up off the gurney, as far as the restraints would let him go. He kept trying to speak but couldn’t form the words, and he rolled his head back and forth.

Zellmer watched the monitor. The potassium chloride was supposed to stop Lockett’s heart immediately, by disrupting the electrical charge that causes the heart muscles to contract. But although Lockett’s heart was slowing, it kept beating.

The normal resting heart rate for an adult is between 60 and 100 beats per minute. Lockett’s dropped into the 20s. From the waves on the screen, it looked like his heart muscles were starting to fire erratically. The doctor thought Lockett might be starting to seize. But he still felt uncertain of his role, and hesitated to intervene.

Finally Lockett managed to speak: “Man.”

Zellmer had seen enough. He came to the gurney and lifted the sheet. Underneath, he saw a protrusion almost the size of a tennis ball on Lockett’s groin.

From the viewing area, Katie Fretland could see the doctor’s face for the first time, and his expression was clear: Oh, fuck. Another witness saw Lockett open his eyes and look right at the doctor, like something out of a horror movie.

The warden glanced under the sheet and noticed what looked like blood and clear liquid pooled around Lockett’s groin. She looked up and addressed the witnesses: “We’re going to lower the blinds, temporarily.”

From the chemical room, the paramedic heard someone say, “He’s trying to get off the table!” She came into the death chamber as the doctor was trying to figure out how to finish the execution.

“I need to get another IV in the left femoral,” Zellmer told her. She swabbed Lockett’s groin with a sterile pad.

“Take deep breaths,” the paramedic told Lockett, in case he could hear her, while Zellmer pushed the short needle back into Lockett’s groin. Blood squirted all over Zellmer, so much of it that it soaked his jacket.

“You’ve hit the artery,” the paramedic said.

“It’ll be all right,” Zellmer told her. “We’ll go ahead and get the drugs.”

Did he intend to put drugs in an artery? The paramedic didn’t want to countermand the doctor’s authority, but that made no sense. “We’ve got to get the vein,” she said. The doctor pulled out the needle.

Lockett mumbled incoherently. His heart rate dropped into the teens as more of the potassium chloride that had been pumped into his groin seeped into his bloodstream. Eventually, the doctor and the paramedic stopped what they were doing.

The warden asked whether it would be possible to resuscitate Lockett. Zellmer said he could start CPR, but that in order to save him, they’d have to take him to an emergency room. This further confused the paramedic. He’s dying, she thought. Isn’t that why we’re here?

Stephanie Neiman’s family was in shock. After the blinds came down, prison staff took them to a rec room and tried to console them. While Neiman’s mother, Susie, wept, someone from the state attorney general’s office tried to explain what had happened, something about Lockett’s heart and a vein exploding. Susie said she wanted to go into the chamber and touch Lockett; otherwise she couldn’t know for sure that her daughter’s killer was dead.

Fretland and the other reporters felt almost as stunned. In the viewing area, a black telephone she hadn’t noticed before started ringing. Robert Patton, the Oklahoma Department of Corrections director, picked it up and left the room, pulling the phone cord out into the hall and closing the door behind him.

Warden Trammell was calling from the death chamber. Patton asked her, “Has enough drugs been administered to cause death?” He heard Trammell repeat the question. He heard the doctor say no.

“Is there another vein available, and if so do you have another set of chemicals back there?” Again, Trammell repeated the question; again the doctor said no.

“I wanna be real clear with this, Warden, and I want you to ask the doctor specifically. Has enough drugs entered the inmate’s system to cause death?” A third time, he heard Trammell repeat the question. A third time, the answer was no.

Patton hung up the phone and huddled in the hallway with the state secretary of safety and security and two members of the attorney general’s office. Someone briefly floated the idea of using the drugs reserved for Charles Warner’s execution. Patton spoke on the phone with the governor’s general counsel, Steve Mullins, in Oklahoma City.

Mullins asked Patton, “Do you want to stop the execution?”

“Yes.”

“You have the authority to stop the execution,” he told Patton.

When they hung up, Mullins called the governor—the basketball game was now an hour from tip-off—to brief her.

At 6:56, a call came in to the death chamber. Patton had instructions for the warden. He said something like “stand down,” which Trammell didn’t quite understand.

“Do you mean to stop?”

Yes, he said, stop the execution.

"I believe the death penalty is an appropriate response and punishment to those who commit heinous crimes," Oklahoma Governor Mary Fallin said at a press conference the day after Lockett's execution. (Alonzo Adams / AP)

Ten minutes later, at 7:06 p.m., Clayton Lockett was declared dead. He had been dying amidst all the chaos, just very slowly and in apparent agony.

The next day, Governor Fallin gave a press conference to remind everyone about Lockett’s crimes, voice her support for the death penalty, and announce an investigation into what had gone wrong. Later in the week, a reporter asked President Obama about Lockett’s execution. Obama called the events “deeply troubling.” He maintained his support for the death penalty but added, “We do have to, as a society, ask ourselves some difficult and profound questions” about how it is applied.

Mark Gibson, the prosecutor, doesn’t consider what happened to Lockett a tragedy. “If there is ever somebody who deserved it, it was him,” he says.

Two separate autopsies were conducted. The results of one suggested that Lockett’s struggles against the restraints had been so violent that they’d caused blunt-impact injuries. Neither autopsy explained why it had taken the doctor and the paramedic so many tries to place an IV; there was nothing wrong with Lockett’s veins. The pathologists also found that the amount of midazolam that had made it into his bloodstream should have been enough to render him fully unconscious.

An attorney for Lockett’s family, David Lane, filed a lawsuit in federal court against Governor Fallin, prison officials, and Zellmer, as well as the unidentified paramedic and executioners, two drug manufacturers, and two compounding pharmacies for violating the Eighth Amendment and standards of international law. Lane characterizes what happened to Lockett as “human experimentation.” The named defendants have filed motions to dismiss, which, as of this writing, are still before the court. (The Oklahoma Department of Corrections declined to grant interviews for this article, citing the pending litigation.)

Charles Warner’s execution had been delayed that night, and it was delayed two more times while the state finished investigating Lockett’s execution, and while officials tried to find more drugs. In July, Arizona used midazolam in the execution of Joseph Wood. He took nearly two hours to die, and witnesses reported that he gasped throughout.

Lawyers for Warner and three other men on death row asked the U.S. Supreme Court to review Oklahoma’s lethal-injection method. They also asked for a stay while the Court decided whether to take the case.

On the night of Warner’s execution, January 15, 2015, the Court still had not ruled on the stay request. The execution was delayed by an hour as the justices made their decision. They were one vote short of the five needed to grant a stay.

Witnesses said Warner didn’t appear to be in any pain, but after the midazolam was administered, he said, “My body is on fire.” He died in 18 minutes.

The next week, even though Warner, the lead petitioner, was now dead, the Supreme Court decided to consider the challenge to Oklahoma’s lethal-injection method. Oral arguments were scheduled for April 29, the one-year anniversary of Lockett’s death. Warner’s co-complainants have been granted stays until the Court decides the case or Oklahoma changes its execution method. Then–U.S. Attorney General Eric Holder recommended that all states stop executions, at least until the Court issues its ruling.

That decision is expected in June.