Now, the state's first lethal injection attempt since then is running dangerously close to another execution night mess.
The problem with Morales in 2006 was a failure to find medical professionals to assist with the execution.
This time, Albert Greenwood Brown is scheduled to die at 9 p.m. Thursday -- just three hours before the Friday expiration date of the state's entire supply of sodium thiopental, a sedative used to knock out inmates before they are fatally injected with two other drugs.
In addition, a state appellate court ruling that cleared the way for the execution doesn't take effect until Thursday.
The drug issue was spotlighted late Monday, when the 9th U.S. Circuit Court of Appeals ordered U.S. District Court Judge Jeremy Fogel to reconsider his decision refusing to block the execution.
"After a four-year moratorium on executions in California, multiple proceedings in federal court, a state administrative law proceeding, and state court appeals, it is incredible to think that the deliberative process might be driven by the expiration date of the execution drug," the appeals court said.
Legal maneuvering has accelerated with the approaching execution of Brown, who was convicted of abducting, raping and killing a 15-year-old girl on her way home from school in 1980.
The appeals court said Fogel needed to take more time than he did to assess the state's new lethal injection procedures adopted last month.
Fogel then gave attorneys just six hours to file legal arguments addressing whether the procedures avoided imposing cruel and unusual punishment.
In his response, David Senior, one of Brown's attorneys, attacked the narrow window of opportunity for the execution as having a "Cinderella quality."
Senior told Fogel the "fiasco" was created when the attorney general's office sought to execute someone soon after the new lethal injection regulations were adopted on Aug. 29.
"It appears they were so desperate to execute that they were seeking dates of execution even when they knew they wouldn't have the drugs to perform them, or were unaware of this," Senior wrote. "It is hard to figure out which is worse."
Deputy Attorney General Michael Quinn, the lead government attorney handling the execution, said he didn't know when prison officials had told him of the problem with the sodium thiopental. Quinn declined further comment and referred calls to the attorney general's press office, which in turn referred questions to the Department of Corrections and Rehabilitation. Prison department spokeswoman Terry Thornton declined comment.
In his filing to Fogel, Quinn didn't address the issue of expiring drugs. Instead, he urged the judge to allow the execution to proceed, arguing the state's new lethal injection regulations protect inmates from pain.
It was Fogel who ordered a halt to California executions in 2006 and ordered prison officials to overhaul the lethal injection process.
Prison authorities responded by building a new death chamber, overhauling the way executions teams are selected and trained, and making several other changes to its lethal injection procedures to comply with Fogel's order.
Last Friday, Fogel refused to block Brown's execution, saying it appeared the state had made significant process in improving its procedures.
In its push to execute Brown, the attorney general's office sought a pre-emptive order Monday from the state Supreme Court that the state appeals court ruling clearing the way for the execution would become final at 5 p.m. Thursday.
Deputy Attorney General Michael Quinn acknowledged he was seeking extraordinary relief in asking the high court to take action.
But he said the impending expiration of the sodium thiopental supply left him with no alternatives if Brown is to be executed on schedule.
The state's regulations call for each condemned inmate to receive two 1.5-gram injections of sodium thiopental. If the warden determines Brown is still awake, he would receive two more shots of 1.5 grams, according to the state's regulations. The state has only 7 grams on hand.
Once unconscious, Brown would be injected with pancuronium bromide and potassium chloride, which should prove fatal.
Even if Brown is put to death, it's unlikely any more executions will be set until next year, when officials hope to receive a new batch of the sedative. Hospira, the company that makes the drug, said it has encountered production problems and can't deliver a fresh supply until early next year.
Authorities previously canceled a hearing that had been planned Sept. 14 in Ventura County to set an execution date for inmate Michael Morales.
Brown is one of several death row inmates who have lost all of their trial appeals and is eligible for execution. Brown is the first in line because the Riverside County district attorney asked a court for an execution the day after California adopted its new lethal injection regulations.
Judge Fogel, attorneys for Brown and death penalty watchers were caught by surprise when Riverside County prosecutors -- assisted by lawyers from the attorney general's office -- obtained an execution date during an Aug. 30 hearing.
Riverside County prosecutors had pushed the judge for a Sept. 29 execution date with no mention of the drug expiration issue. Riverside County District Attorney Rod Pacheco said Tuesday his office was first informed this week of the issue.
"How is this possible? This is ridiculous," said Pacheco, still optimistic the execution would proceed. "I'm a little frustrated. The death penalty in California is becoming surreal."