As questions linger about Missouri's shadowy lethal-injection protocol, the state is days away from killing another inmate.

As questions linger about Missouri's shadowy lethal-injection protocol, the state is days away from killing another inmate 

As questions linger about Missouri's shadowy lethal-injection protocol, the state is days away from killing another inmate.

click to enlarge EXECUTION.jpg

Chris Gash

At 10:52 p.m. December 11, the Missouri Department of Corrections executed Allen Nicklasson with a single, lethal drug dripped into the convicted murderer's veins.

Just before the dose was administered, Missouri Attorney General Chris Koster issued a statement to the media saying that "the highest court in the nation has removed the last restriction to carrying out the lawfully imposed punishment of Allen Nicklasson."

Except, for the second time last year, that wasn't quite the case.

"Missouri put Nicklasson to death before the federal courts had a final say on whether doing so violated the federal constitution," said Judge Kermit Bye, of the 8th U.S. Circuit Court of Appeals, in a December 20 opinion.

Bye, a federal appellate-court judge since 1999, said the 11 judges on the 8th Circuit had not yet voted on Nicklasson's request for a stay of his execution.

Missouri put Nicklasson to death before his due process had been fully resolved.

A death-row inmate's gauntlet of appeals often takes years, and Nicklasson's run through the courts was no exception. He was sentenced to death in 1996. Death-penalty proponents say the appeals process is expensive and drags out the suffering of victims' families. But that process is designed to safeguard against the possibility of an innocent person suffering an irreversible fate — and to ensure that the death penalty is administered properly.

There was no question of innocence in Nicklasson's case. He had admitted to shooting Excelsior Springs businessman Richard Drummond in the middle of a 1994 crime spree, after Drummond offered to help Nicklasson and Dennis Skillicorn with their broken-down car. Rather, Nicklasson's attorneys were trying to figure out where Missouri would obtain the drug it intended to use on him. Is that drug, they wanted to know, suitable to kill a prisoner with a right to avoid a painful death? Nicklasson died before he got those answers.

So did serial killer Joseph Franklin. When Franklin was executed November 20, he, too, was still awaiting a final ruling from a judge on whether his attorneys could learn more about Missouri's death-penalty protocol.

"I think that because they didn't let the courts do what they were supposed to do, it undermines the authority of the court," says Rita Linhardt, board chairwoman for Missourians for Alternatives to the Death Penalty. "It's setting Missouri above the law that the court isn't allowed to do what it's allowed to do."

Bye's opinion has attracted newfound skepticism of Missouri's whack-a-mole execution methods.

State Rep. Jay Barnes, a Republican from Jefferson City, called for a hearing before the Missouri House committee on Government Oversight and Accountability over whether the state is affording condemned prisoners their due process before their executions. "Regardless of what anyone thinks of the death penalty, everyone should agree that it must be carried out according to the requirements of the Constitution and the laws of our state," he said in a January 13 statement.

That hearing was canceled when George Lombardi, director of the Missouri Department of Corrections, declined to testify.

Rep. John Rizzo, a House Democrat from Kansas City, has called for a one-year moratorium on Missouri's death penalty while the Legislature studies the Department of Corrections' actions.

But that scrutiny hasn't slowed the Department of Corrections. Herbert Smulls is the next death-row prisoner set to die. His execution is scheduled for January 29.

"The trend nationwide is away from executions, and Missouri is jumping into this full force," Linhardt says.

Missouri officials are staying quiet publicly. The Department of Corrections, Koster's office and Gov. Jay Nixon's office have all either declined or ignored The Pitch's requests for comment on Bye's decision and other questions about Missouri's death-penalty practices.

Ahead of Smulls' execution, though, a lawsuit is under way in the U.S. District Court in Kansas City, as well as in the 8th Circuit in St. Louis. Attorneys for several condemned prisoners are asking those courts to cast light on Missouri's shadowy death-penalty methods.

So far, lawyers suing the state believe that Missouri has purchased its lethal-injection drug from a compounding pharmacy in Oklahoma that is not licensed to do business in Missouri.

The state of Missouri, responding to an open-records request, disclosed a heavily redacted copy of a license from the pharmacy from which it obtained pentobarbital. Two things not redacted were the date upon which the license was issued (November 16, 2012) and the fee paid for the license ($255). 

The Pitch obtained from the Oklahoma Board of Pharmacy a list of licenses processed on that date.

Three Oklahoma pharmacies on that day received the type of license and the specific combination of permits shown on the redacted license released by Missouri, and made the $255 payments. One was Pharmcare in Hydro; another was Economy Pharmacy in Muskogee; the third was the Apothecary Shoppe in Tulsa.

The Pitch called pharmacy technicians at all three businesses and asked if they performed sterile injectable compounding, a method through which compounding pharmacies make drugs suitable for injections. Technicians at Pharmcare and at Economy Pharmacy said they did not; a pharmacy clerk at Apothecary Shoppe said the company did. 

The Pitch reached Apothecary Shoppe CEO Deril Lees on January 20. When asked if the pharmacy had ever supplied Missouri with pentobarbital or had a contract with Missouri, Lees said no.

"There are serious questions about the integrity of the pharmacy," says Tony Rothert, legal director of the American Civil Liberties Union of Missouri. "If you wanted to buy a drug from an [unlicensed] out-of-state pharmacy for a controlled substance, you'd be put in jail."

Compounding pharmacies, unlike conventional drug makers, exist outside the reach of the stringent federal regulatory framework. They operate in the murky "gray market" of the pharmaceutical industry — theirs is not an illegal black market but one in which a product's origins are untraceable and beyond the watch of the U.S. Food and Drug Administration. It's often difficult to determine in advance the potency of a compounding pharmacy's product or whether it's contaminated or impure.

In 2011, the Missouri Board of Pharmacy tested 158 compounded drugs from various pharmacies. It found that 17 percent failed its potency test.

Why does anyone care where the Department of Corrections gets its drugs? The primary concern is whether condemned inmates suffer painful and unconstitutional deaths by lethal injection — something that has almost surely happened in Missouri.

Missouri's first lethal-injection machine was designed by a Nazi sympathizer.

Fred Leuchter was the only bidder in 1990, after Missouri resumed the death penalty in 1989 and needed a device to administer fatal drugs. He had no formal training in medicine or engineering, but that didn't stop him from advertising his invention as an effective means of capital punishment at a time when previous methods were falling out of favor.

The Constitution protects Americans from cruel and unusual punishment, and by the 1970s and 1980s, electrocuting or gassing inmates to death was widely considered problematic. In 1928, photojournalist Tom Howard sneaked a camera into New York's Sing Sing Prison and snapped a photo of Ruth Snyder at the moment she received a fatal jolt of electricity. Howard's grotesque document of Snyder — hooded and strapped to the electric chair — ran on the front page of the next day's New York Daily News and gave the world a glimpse of state-sanctioned death.

After that came consistent reports of inmates screaming as currents ran through their bodies and of the odor of burning flesh. Florida dispensed with its electric chair after the 1999 execution of Allen Lee Davis, who witnesses said convulsed and bled while being electrocuted. The Florida Supreme Court later released troubling photos of Davis that showed what was under his hood when prison officials lifted it: a bloodied face mashed against the leather strap meant to keep his head still.

The gas chamber didn't make a suitable replacement; inhaling cyanide gas proved to be a painful way for some inmates to die.

Lethal injection, first used by Texas in 1982, was proposed as humane and painless. An inmate would receive a drug and drift off into a medically induced slumber, as though waiting to have a molar pulled. Some death-penalty critics opposed lethal injection because they didn't want Americans to have the illusion that state-sanctioned death was a clean procedure.

The lethal-injection machine that Missouri bought from Leuchter was designed to pump three drugs into an inmate: one to knock him out, another to paralyze him, and the last to end his life.

Everybody but the Missouri Department of Corrections had written off Leuchter, whose credibility was shredded when he offered his testimony in support of anti-Semite Ernst Zündel in 1988. Zündel was on trial that year in Canada, where it is illegal to antagonize ethnic and racial groups with bogus information. He had published Richard Verrall's pamphlet "Did Six Million Really Die?" that questioned whether Jews were exterminated by Nazi Germany before and during World War II.

Leuchter was one of the chief experts testifying on Zündel's behalf, presenting so-called evidence denying the Holocaust. The minimal scientific veneer of his testimony was undercut when his phony engineering credentials were exposed, and Leuchter was charged in Massachusetts in 1990 for running an unlicensed engineering practice. A New York Times article about Leuchter's legal troubles reported that an anesthesiologist in Illinois had testified that Leuchter's lethal-injection protocol would "paralyze inmates and cause them intense pain before they died."

Missouri ultimately canceled its contract with Leuchter but pushed on with a similar three-drug protocol, despite experts' misgivings about whether a method that presented itself as antiseptic and painless was actually an excruciating way to die.

The first drug to enter an inmate's veins was sodium thiopental, a fast-acting anesthetic commonly used in outpatient surgeries to induce unconsciousness. It's not as strong as general anesthesia, though, and is prone to wearing off. The next drug was Pavulon, which paralyzes muscles. Finally, potassium chloride was used to stop the inmate's heart.

But questions persisted about inmates receiving enough of the sodium thiopental. Without an adequate dose, death would be painful, and expression of that pain would be impossible because of the paralyzing Pavulon.

Carol Weihrer, a Virginia resident, became the spokeswoman for what is now called anesthetic awareness when the sodium thiopental she was given for an eye surgery in 1998 wore off before her doctors completed the procedure. She sent written testimony to the Pennsylvania House of Representatives in 2005 that described her experience.

"I remember the intense pulling on my eye, the spine-chilling instructions of the surgeon to the resident to 'cut deeper here, pull harder, no pull harder, you really have to pull.' I remember fighting with every ounce of energy and thought process I had to let the surgical team know I was awake," she recalled.

Sean O'Brien, a University of Missouri–Kansas City School of Law professor and frequent legal counsel to death-penalty inmates, says he first became interested in the potentially painful effects of lethal injection when Missouri executed Emmitt Foster in 1995.

In those days, Department of Corrections personnel involved in the execution would shout "foxfire one" when the first drug began its flow to the inmate, "foxfire two" when the next drug was pushed, and "foxfire three" when the fatal drug began its course. "Checkmate" was the word when the inmate was pronounced dead.

O'Brien says when the first drug reached Foster, the inmate started coughing and twitching. Something seemed amiss. Prison officials closed the curtain to the window that allowed witnesses to observe the execution.

A prison official realized that a strap was restricting the flow of drugs to the rest of Foster's body. The band was removed, and Foster took 30 minutes to die.

The April 16, 2005, edition of the weekly medical journal The Lancet analyzed autopsy and toxicology reports of 49 executed inmates. It found that 43 of them had received doses of sodium thiopental lower than the standard for surgery, and that 21 had received such a low dose that they could have been aware of what was happening to them.

"That is: those being executed may have been awake," the report's abstract reads. "Of course, because they were paralyzed, no one could tell. It would be a cruel way to die: awake, paralyzed, unable to move, to breathe, while potassium burned through your veins."

The same report pointed out that the American Veterinary Medical Association and 19 states ban the use of drugs such as sodium thiopental in the killing of animals. In other words, the drugs that can be used in a state-sanctioned execution of a human are in some places deemed unsuitable to put down a dog with an untreatable case of heartworm.

The Lancet article came out a month ahead of Vernon Brown's scheduled execution in Missouri. His lawyers used the journal's findings as the basis to ask the state how much sodium thiopental it planned to use in Brown's execution. But Missouri fought Brown's attorneys in court, ultimately killing Brown without having to tell him how much of a drug they were going to give him.

The concern was well-founded. The following year, it was discovered that a doctor who had assisted in 54 Missouri executions was dyslexic and, according to his testimony, had improvised the dosages.

Missouri corrections officials couldn't keep the doctor from testifying in front of a federal judge, but they succeeded in obscuring his name from the public record.

A federal judge in Kansas City was furious about the doctor's testimony and lamented that Missouri lacked a written protocol for its lethal injections. He ruled that the state needed to come up with a better lethal-injection method and to stop using the doctor in question.

Despite the state's secrecy, reporters with the St. Louis Post-Dispatch figured out that the dyslexic doctor was Alan Doerhoff, a physician who had been reprimanded by the Missouri Board of Registration for the Healing Arts for trying to hide the fact that he had been sued for malpractice.

Missouri's embarrassment over the Doerhoff affair slowed the state's death-penalty pipeline. The state didn't execute another prisoner until Dennis Skillicorn, in 2009.

Missouri's capital-punishment methods returned to the international limelight in 2013, when the state prepared to execute Joseph Franklin. He was an admitted mass murderer, but his case attracted attention from someone he didn't kill.

Larry Flynt, the pornography magnate who doubles as a free-speech proponent and anti-death-penalty activist, has been in a wheelchair since 1978. That was when Franklin, a white supremacist who took exception to Flynt's Hustler magazine showing photo spreads of interracial sex, shot Flynt and a lawyer in Georgia. Flynt and the American Civil Liberties Union sued to find out which medical personnel were participating in executing Missouri's condemned.

Doctors are supposed to save lives and are thus prohibited by virtually all professional codes of conduct from helping with an execution.

Flynt's lawsuit didn't stop Franklin's execution. But it was the European Union that temporarily stalled Missouri's death penalty.

Missouri had dispensed with the old three-drug method and was planning to kill Franklin with a drug called propofol.

Propofol, used as a relaxant and an anesthetic, is coveted by hospitals and doctors in the United States. It's manufactured mostly in Germany, where capital punishment is illegal. When the Germans caught wind of Missouri's plans to use propofol, the European Union threatened to stop exporting the drug to the United States.

Several medical associations expressed annoyance at the prospect of a propofol shortage if the state pressed on with the drug for Franklin's execution. That got Missouri Gov. Jay Nixon's attention. He delayed the execution until the state could figure out another way to kill Nicklasson.

Some states' use of federally approved drugs against the wishes of their manufacturers has resulted in something of a shortage of drugs that have other legitimate medical functions.

Joel Zivot, a medical director and an anesthesiologist at Emory University School of Medicine in Atlanta, wrote in a December 16 editorial published in Ohio's Lancaster Eagle-Gazette that drug maker Hospira stopped producing sodium thiopental in protest of states using the drug in executions. This left him without access to the medicine: "States may choose to execute their citizens, but when they employ lethal injection, they are not practicing medicine. They are usurping the tools and arts of the medical trade and propagating a fiction."

With propofol out of the picture, the Missouri Department of Corrections changed its execution protocol several times in the weeks leading up to Franklin's execution, a move that frustrated attorneys representing Franklin and other inmates.

On October 18, the state proposed using pentobarbital. On November 15, it changed the execution recipe again, five days before Franklin was scheduled to die. That left little time for lawyers to investigate what the drug was and where Missouri was getting it. Franklin's attorneys made a motion before the U.S. District Court in Kansas City to stay his execution, but he died November 20, before a judge could get to that motion.

The shell game that preceded Franklin's execution, coupled with Missouri's secrecy over how it plans to carry out future executions, is the subject of intense litigation in the U.S. District Court in Kansas City — just days before Herbert Smulls is scheduled to die.

Modern capital-punishment laws have typically kept the identity of the executioner secret. The stigma attached to ending someone else's life, even in a state-sanctioned execution, has enabled governments to justify obscuring an executioner's name from public view.

Until 2010, Utah used a firing squad for some of its executions. The custom called for five rifle shooters to aim at the prisoner. One of the five guns was loaded with the rough equivalent of a blank cartridge to ease each shooter's conscience; each man could doubt whether he had fired one of the lethal shots.

Missouri laws also keep secret the names of members of the state's execution team, which includes not only the person who administers the fatal dose but also those who assist that person. Missouri officials have tried to expand that cloak to include the pharmacy that makes the execution drug and the pharmacist who writes a prescription for the fatal dose. Attempts by attorneys for death-row prisoners to learn the whereabouts of the state's drug supplier were met throughout 2013 by resistance from the Missouri Attorney General's Office and the Department of Corrections, which insisted that Missouri law allowed corrections officials to keep the drug supplier secret as part of the execution team.

Toward the end of 2013, state officials deployed the "state secret" privilege to convince federal judges to affirm the shield around the death team. It's a legal concept normally used in matters of national security, intelligence gathering, and budgets for federal organizations such as the National Security Agency and the Central Intelligence Agency.

That led to a December 12 teleconference among U.S. District Judge Nanette Laughery and attorneys for both prisoners and Missouri officials. Joseph Luby, a lawyer with Kansas City's Death Penalty Litigation Clinic, reminded Laughery of his legal team's Catch-22.

"The only scientific expert that is present in this case says that we actually do have a need to know who it is that is supplying these drugs, who has compounded them, so that we have an idea of what it is that the state is administering and seeking to administer in the future," Luby said, according to a transcript of the conversation. "Otherwise, we don't know where the active pharmaceutical ingredient comes from, how it was manufactured, the circumstances under which it was compounded, what impurities might exist and what hazards are involved in administering it."

The scientific expert whom Luby referenced was Larry Sasich, chairman of the pharmacy practice at the Lake Erie College of Osteopathic Medicine in Pennsylvania and adviser to the Food and Drug Administration commissioner. Sasich offered a lengthy affidavit outlining the potential hazards of compounded drugs: "The potential harm associated with the use of such contaminated or sub-potent drugs is extremely high. Consumers who use compounded drugs do so at their own risk."

Andrew Bailey, a lawyer representing the Missouri Department of Corrections, reiterated the need for secrecy to protect the safety of those involved with an execution. He cited the slaying of a former Missouri Department of Corrections official a year ago.

He didn't name the victim, but he was likely talking about Tom Clements, the longtime Department of Corrections director who took the same position in Colorado in 2011. He was killed at his home in March 2013 by a man who investigators believe was a white supremacist and may have been carrying out an assassination.

But Clements' identity and responsibilities were widely known. The issue of secrecy wasn't a factor in his death.

Bailey pressed on, saying that disclosing the identity of the drug supplier would have no effect on whether the state could carry out an appropriate execution.

"The director [Lombardi] has stated that he will not use chemicals that aren't pure, potent and sterile and the director's administered two successful executions at this point," Bailey said.

Laughery didn't find the state's position persuasive. She rejected both the state-secrets argument and the notion that Missouri law required that the pharmacy remain secret.

"The balance clearly weighs in favor of revealing the information to the plaintiffs [prisoners] because it's impossible for the plaintiffs to meet the burden of proof established by the courts in the absence of those elements," Laughery said. She ordered the Missouri Department of Corrections to hand over information about its drug supplier, the pharmacist writing the prescription, and the lab reports about the drug to Luby and to Cheryl Pilate, a Kansas City lawyer who is part of the death-row-inmate legal team.

The information was supposed to go to Luby and Pilate and no one else.

Missouri officials tried to get Laughery to change her mind on December 16, but she didn't and instead reiterated that Missouri must release its drug-supplier records.

Pilate on December 16 sent several e-mails to Department of Corrections lawyers, asking for the information she was expecting. She sat before her computer until midnight, waiting for information that never came.

Attorneys for Missouri kept resisting disclosure while trying to get the 8th Circuit to reverse Laughery's decision.

In an odd twist, Missouri officials did send their information to Laughery's office. And in an odder twist, Laughery sent the information to Pilate and Luby on December 28, not knowing that, the day before, the 8th Circuit had said to hold off.

Once Laughery realized that a higher court had intervened, she told Pilate and Luby to sit tight with any knowledge they had gleaned from her disclosure. On December 30, she held another teleconference with all of the lawyers involved. She told Pilate and Luby not to act on anything they had learned from the Department of Corrections' file and to scrub any record of it from their files and computers.

That left attorneys representing condemned prisoners with knowledge of a key piece of information — the identity of a pharmacy they fought in court for more than a year to discover — but unable to investigate it further.

Laughery recused herself from the case on December 30.

"We have a pharmacy in Oklahoma that is manufacturing chemicals and importing them into Missouri in violation of Missouri and federal law and possibly in violation of the intellectual rights of pentobarbital's manufacturer," says UMKC's O'Brien.

Meanwhile, the tortured legal proceedings over whether prisoners are allowed to know where Missouri's death-penalty drugs comes from is in limbo while a new judge, former Kansas City U.S. Attorney Beth Phillips, gets up to speed. A trial is scheduled for June 16.

That leaves unresolved the fate of Herbert Smulls. Will his attorneys persuade the state or federal judges to delay his January 29 execution while the peculiarities surrounding Missouri's death penalty get sorted out? Will Missouri give federal judges enough time to figure it out?

At least one appellate judge may stand in Missouri's way.

Judge Kermit Bye wrote in a biting December 20 opinion: "Missouri's ... current practice of using shadow pharmacies hidden behind the hangman's hood, copycat pharmaceuticals, numerous last-minute changes to its execution protocol and finally, its act of proceeding with an execution before the federal courts had completed their review of an active request for a stay has committed this judge to subjecting the state's future implementation of the penalty of death to intense judicial scrutiny, for the sake of death-row inmates involved as well as adversaries and advocates for capital punishment alike."

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