Updated 11:05 pm 12/11/13
Late Wednesday evening, the U.S. Supreme Court vacated a stay of execution for Missouri inmate Allen Nicklasson. Shortly later, the Department of Corrections carried out the execution.
Gov. Jay Nixon denied clemency, and soon after 10 pm, the attorney general said the execution was clear to proceed. It was the second execution under the state's controversial new rule that hides the identity of the supplier of the drug.
The inmate was put to death for the killing of Richard Drummond, who stopped on the side of the road to help Nicklasson.
Earlier this week, federal judges issued a stay of execution, pertaining to the inmate's claim of ineffective counsel in his original trial and appeal. The state appealed that stay. After the 8th Circuit refused to consider lifting the stay, the ruling made its way to the Supreme Court.
Although the state had hoped to carry out the execution early Wednesday morning, the death warrant was valid the whole day. The Supreme Court removed the stay with just a couple hours left.
At the same time, another federal judge is hearing a case on the constitutionality of Missouri's new execution method. We've reported extensively on the new rule, and how the state's secrecy and drug source could mean the Department of Corrections could use a drug that isn't sufficiently potent.
"The use of anonymously compounded pentobarbital puts Mr. Nicklasson at risk of an excruciatingly painful execution," Nicklasson's lawyers write.
In 2012, a group of anti-death penalty lawyers filed a lawsuit questioning Missouri's execution methods. Since the state has changed its method numerous times in the past few months, the merits of that case haven't been ruled on. Nicklasson's lawyers say that since he stands a fair chance of winning that case, his execution should be postponed.
His lawyers are also asking for sanctions against the state for not providing documents vital to the case.
"Their conduct has been intentionally dilatory, unethical, unworthy of the people of the state of Missouri, plainly reprehensible, and clearly calculated to deprive plaintiffs of due process of law," the lawyers wrote in a motion filed Tuesday.
The sanctions would force the Department of Corrections to hold off on executions until the state produces the documents the lawyers are asking for in the case.
That suit is before Judge Nanette Laughrey, who had sharply reprimanded the state for its conduct in the prior execution. She took issue with the Department of Corrections changing its execution method numerous times before the execution date, and then arguing that the case was moot because the method had changed.
"The defendants keep changing the protocol that they intend to use," Laughrey wrote in November. "It would be a substantial departure from the way in which law suits are generally handled by this court, to allow defendants to succeed with this strategy. Litigation is not a game of chess."
But her stay was overturned by higher courts last month. So on Wednesday, Laughrey denied a motion for a stay of execution, citing the ruling in last month's execution. In her order, Laughrey called it a "Catch-22."
"A stay of execution is not appropriate because Mr. Nicklasson has failed to show a demonstrated risk of harm and can only offer speculative allegations," Laughrey wrote. "But, Mr. Nicklasson has had no opportunity to show a demonstrated risk of harm because the protocol in this case has changed so recently and frequently and because the identity of the pharmacist is secret and the testing of the actual drug to be used has only been revealed in the last few days and only updated a few hours ago. Nonetheless…this court is bound by (the Supreme Court’s) ruling."
Nicklasson's lawyers have appealed Laughrey's ruling to the 8th Circuit Court of Appeals, which previously denied the stay.
In court filings last Thursday, the state detailed the reasons the courts shouldn't postpone the execution.
Attorney General Chris Koster and his office focused heavily on jurisdiction -- arguing that the federal courts don't have rule over this case since the Department of Corrections has changed its execution method.
Koster's filing did not address the claim that using drugs from a secret compounding pharmacy would put the inmate at a greater risk of a slow and painful death.
Compounded drugs aren't regulated by the Food and Drug Administration like manufactured drugs are.
As far as the secrecy, Koster's office defended keeping the supplier confidential. State filings complain that it's hard to get execution drugs since most private businesses don't want their products to be used for lethal injections.
Koster points to Texas, where a compounding pharmacy supplied the Lone Star State with an execution drug, but asked for it back when their name got out.
"It was my belief that this information would be kept on the 'down low' and that it was unlikely it would be discovered that my pharmacy provided these drugs," the Texas pharmacy wrote, asking for the drugs back.
You can read the motion to stay the execution below, as well as the state's response.
Follow Chris McDaniel on Twitter: @csmcdaniel