On the night of Feb. 22, Doyle Lee Hamm lay strapped to a gurney, hoping to die. Earlier that evening, the Supreme Court had voted 7–2 to let Hamm’s execution proceed despite grave doubts about the ability of executioners to access his compromised veins. Those doubts proved prescient. For several hours, employees of the Holman Correctional Facility in Alabama stuck needles in Hamm’s body in an effort to flood his veins with deadly drugs. They allegedly punctured his bladder and femoral artery, releasing a torrent of blood. But the executioners were unable to find a suitable vein for lethal injection. At 11:30 pm, they gave up, sending the still-conscious Hamm back to death row, where he has languished for 30 years.

“I wouldn’t necessarily characterize what we had tonight as a problem,” Alabama Department of Corrections Commissioner Jeff Dunn told reporters shortly thereafter.

Hamm’s botched execution is not the first time that American executioners have tortured an inmate on the gurney. But it does raise a relatively novel legal question: Now that Alabama has tried and failed to kill Hamm once, does it have the constitutional authority to try again? Supreme Court precedent provides no clear answer. And Hamm’s attorney, Bernard Harcourt, may now have a real shot at saving the life that Alabama could not extinguish.

Harcourt has represented Hamm since 1990, just three years after Hamm was sentenced to death for killing a night clerk during a motel robbery. There are numerous irregularities in Hamm’s case: His earlier attorney, William Travis Gobble, ignored mitigating evidence—including severe childhood abuse and brain damage—that might’ve persuaded a jury to spare Hamm’s life. Gobble also failed to investigate Hamm’s prior conviction for a robbery—a crime that contributed to his death sentence, but one which he had not actually committed. The judge who refused to give Hamm a new sentencing hearing on the basis of this evidence issued an opinion that was literally written by prosecutors.

But none of these issues were on the table as Hamm’s execution date drew closer. (Alabama appears to have moved up the date so it could stop treating him for cancer.) Because the courts had foreclosed a new sentencing hearing, Harcourt argued that Hamm’s death by lethal injection would violate the Eighth Amendment’s ban on “cruel and unusual punishments.” Hamm has lymphatic cancer, carcinoma, and Hepatitis C; his cancer treatment, combined with his age (61) and past use of intravenous drugs, have made his veins extremely difficult to access.

Hamm’s botched execution is not the first time that American executions have tortured an inmate on the gurney.

The Supreme Court has ruled that an execution violates the Eighth Amendment when it presents a “substantial” or “objectively intolerable” risk of “serious harm.” It has also held that an inmate who wishes to avoid a certain method of execution must propose a less risky alternative. So Hamm suggests that Alabama kill him using the protocol that Oregon doctors administer to terminal patients under their “death with dignity” law. Alabama refused and fought for the right to kill him through lethal injection.

Harcourt asked Mark Heath, a doctor and professor of medicine at Columbia University, to examine Hamm for usable veins. He found just one, which still had “a high chance of rupturing.” Two U.N. human rights experts also called on Alabama to delay the execution, declaring that failed lethal injection “may amount to torture.” But the prison procured its own doctor, who declared that several of Hamm’s veins could be accessed. On the advice of this doctor, a federal judge allowed the lethal injection to move forward. Over the dissent of Justices Sonia Sotomayor and Ruth Bader Ginsburg, the Supreme Court declined to stay Hamm’s execution.

And so, on the night of Feb. 22, prison staff took Hamm to the execution chamber and tied him to the gurney. They began inserting needles into his legs and ankles, to no avail—as predicted, they could not access a vein. The team flipped Hamm on his stomach and slapped his legs to generate a vein, but that didn’t work, either. Having failed to establish “peripheral” venous access, the team decided to attempt “central” venous access, a more complicated (and painful) procedure.

Suddenly, an unidentified man and woman—who wore business suits and no protective clothing other than gloves—took over. The woman used an ultrasound to locate a vein in Hamm’s right groin. Executioners attempted to access the vein but failed and seem instead to have punctured Hamm’s femoral artery as well as his bladder. Blood began gushing out of the wound they had created. Finally, the team gave up. Hamm had been conscious the entire time, silently hoping that the executioners would just “get it over with.” Several executioners unstrapped him and lifted him off the gurney; he promptly collapsed in agony. Over the next few days, he urinated blood and developed a painful infection in his lymph nodes.

Now Alabama wants a do-over. But Harcourt doesn’t think the state deserves a second shot at killing his client. In fact, he argues that another execution attempt would violate the Constitution. Harcourt has clear proof that lethal injection causes Hamm the kind of “needless and “severe suffering” prohibited by the Eighth Amendment. He also asserts that a second execution would run afoul of the Fifth Amendment’s bar on double jeopardy, which forbids the government from putting any person “in jeopardy of life or limb” twice for the same offense.

In 1947, the Supreme Court ruled that attempting a second execution after the first one fails does not automatically violate the Eighth or Fifth Amendments. But the case involved a surprise equipment failure—not willful ignorance on the state’s part—and the court splintered badly in its reasoning. Four justices found that a second execution is permissible only when “an unforeseeable accident … for which no man is to blame” thwarts the first. Justice Felix Frankfurter concurred only in the judgment, holding that “a single, cruelly willful attempt” at execution may violate the Constitution and prevent the state from trying again. Four justices dissented.

Hamm’s case presents an entirely different set of facts. Here, the botched execution was not “unforeseeable,” but predicted. Alabama was well aware that it might wind up torturing Hamm; it moved forward with the execution anyway. As Harcourt notes, Hamm’s failed execution “was caused by the state’s deliberate decision to disregard the significant risk, raised for months prior to the execution, of a botched and bloody execution.” Alabama’s first effort to kill Hamm therefore looks a lot like the “single, cruelly willful attempt” that Frankfurter warned about.

Harcourt is now asking a federal judge to rule that a second lethal injection would infringe upon Hamm’s constitutional rights, thereby sparing his life for the foreseeable future. With luck, the courts will be chastened by their misplaced trust in the state’s previous claims, which have been graphically refuted. Alabama has already ignored medical experts and tortured Hamm once. The Constitution does not give executioners a mulligan.