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Executing people is harder than it sounds. That’s what Ohio discovered in 2009 when it tried to kill Romell Broom, a man who had been sentenced to death for abducting, raping, and killing a 14-year-old girl in Cleveland in 1984. Broom was scheduled to die by lethal injection, but when officials brought him to the death house, the execution team could not find a suitable vein to insert the IV that would deliver the lethal drug. Members of the team, none of whom were doctors, spent two and a half hours jabbing him with needles, to no avail. After an hour, corrections officials managed to bring in a prison doctor with no experience in executions to assist, but that didn’t help either.

After being stuck with needles 18 times, Broom was crying from the pain and emotional trauma. He insisted on seeing his lawyer, who was not allowed to enter the room with him. She eventually contacted state prosecutors, who alerted then-Gov. Ted Strickland about the situation, and the governor halted the execution.

The state tried to reschedule the execution for a week later, but Broom’s lawyers succeeded in blocking it with an appeal over the central question: If someone survives an execution attempt, can a state legally try it again? Or does the process itself constitute such torture that it qualifies as unconstitutional cruel and unusual punishment? Those arguments have been working their way through Ohio’s courts until this week, when the Ohio Supreme Court agreed to hear the case.

Since the Broom debacle, lethal injection executions have become far more controversial, largely due to moves by pharmaceutical companies to stop selling or exporting the drugs to prisons for use in executions. Drug shortages have spawned legal fights over the drug supply, as inmates have sued to keep themselves from being executed with drugs whose origins and make-up the states are working hard to keep secret. And of course, there’s the recent case of Clayton Lockett, whose botched execution turned those hypothetical legal arguments about the potential dangers of such drugs into a reality. (Lockett almost became the second man after Broom to survive a botched lethal injection, as the procedure was halted when it became clear something was wrong. He ended up dying of a heart attack.)

Broom’s case is a good reminder that the drugs are only part of the problem. A bigger issue is the incompetence of the people overseeing the procedure. Doctors are ethically prohibited from participating because helping kill someone violates their Hippocratic oath, so those MDs who do take part often aren’t at the top of their fields. The most famous example of this problem is Dr. Alan Doerhoff, the dyslexic surgeon who oversaw 54 executions in Missouri, despite the fact that he’d been subject to at least 20 malpractice suits and was banned from working in two different hospitals. Others involved in executions often have little or no medical training. Maryland’s death team once included a state trooper forced to retire after refusing to cooperate with an internal investigation after he was charged with assaulting a teenager. Another team member had been suspended for spitting in inmates’ food before it was given to them, according to expert testimony in a federal legal challenge.

Such people are tasked with setting catheters or IV lines in people whose veins are in a pretty sorry state thanks to long histories of IV drug abuse or years of confinement-related obesity. Even before Broom’s tortuous experience, Ohio previously had several troubled executions stemming from problems finding viable veins in the condemned. In 2006, Joseph Clark yelled during his execution, “It don’t work! It don’t work!” His execution took 90 minutes, largely because a vein collapsed after the IV was inserted. A year later, the execution of Christopher Newton took so long that he was even given a bathroom break because officials had spent so much time trying to locate a viable vein.

How the court will rule on Broom’s petition is uncertain. The US Supreme Court has said that “equipment failure” doesn’t equal the wanton infliction of unnecessary pain that would violate a person’s due process rights or equal cruel and unusual punishment. That opinion came in a famous 1947 case involving Willie Francis, an African-American teenager in Louisiana who, at 16, was convicted of murdering a local white pharmacist and was sent to the electric chair.

In 2006, Joseph Clark yelled during his execution, “It don’t work! It don’t work!” His execution took 90 minutes

A drunk prison guard and an inmate from the notorious prison in Angola set up the chair (known as “Gruesome Gertie”) incorrectly. As a result, Francis didn’t die when the switch was thrown. Instead, he screamed from behind the hood, “I’m not dying!” The execution was halted, and he fought the state’s efforts to try to kill him again. His case went all the way to the Supreme Court, which in a 5-4 decision, ruled that a second execution attempt wouldn’t violate Francis’s constitutional rights. The court said:

The cruelty against which the Constitution protects a convicted man is cruelty inherent in the method of punishment, not the necessary suffering involved in any method employed to extinguish life humanely. The fact that an unforeseeable accident prevented the prompt consummation of the sentence cannot, it seems to us, add an element of cruelty to a subsequent execution.

That opinion, which was used for decades to sustain the use of the electric chair despite evidence that it caused violent, painful death, doesn’t bode well for Broom. But the case wasn’t quite as clear cut as the majority made it sound. The deciding vote was cast by Justice Felix Frankfurter, a death penalty foe who nonetheless deferred to the state. He wrote a concurring opinion that expressed great unease with the outcome. He opened the possibility that a different set of circumstances might lead to a different result down the road. Frankfurter was apparently so disturbed by this case and his role in Francis’ demise that he secretly sent his Harvard Law School roommate, a member of the Louisiana bar, to petition the governor of Louisiana to commute the teen’s sentence to life in prison. (He didn’t.)

And unlike Frankfurter, the dissenters in the case saw an execution do-over as a clear-cut constitutional violation. “How many deliberate and intentional reapplications of electric current does it take to produce a cruel, unusual, and unconstitutional punishment?” wrote Justice Harold Burton. “If five attempts would be ‘cruel and unusual,’ it would be difficult to draw the line between two, three, four and five.” He wrote emphatically:

Taking human life by unnecessarily cruel means shocks the most fundamental instincts of civilized man. It should not be possible under the constitutional procedure of a self-governing people. Abhorrence of the cruelty of ancient forms of capital punishment has increased steadily until, today, some states have prohibited capital punishment altogether. It is unthinkable that any state legislature in modern times would enact a statute expressly authorizing capital punishment by repeated applications of an electric current separated by intervals of days or hours until finally death shall result.

Given Ohio’s long and troubled history when it comes to lethal injections, it’s possible that its high court will decide that the country has evolved since the days of Willie Francis. Indeed, under current Supreme Court precedent, Francis’ original death sentence would be illegal as the court has banned the execution of juveniles. One justice currently on the Ohio court, William O’Neill, has already blasted capital punishment as inherently barbaric and invoked Broom in a dissent last year as evidence that lethal injection was unconstitutional. Perhaps his colleagues will decide that trying to kill someone twice by such a method is barbaric, too.