COUNCIL BLUFFS — More than 25 years after his first-degree murder conviction, Jeffrey Ragland will again have a chance to challenge his life sentence.
The Iowa Supreme Court ruled Friday that Ragland can ask the court system to rule on whether the sentence, because he was a juvenile at the time it was imposed, is cruel and unusual punishment under the state and federal constitutions.
Ragland was 17 when he was convicted of first-degree murder in 1986.
Timothy Sieff, 19, of Omaha died from head injuries after being struck with tire iron during a fight in the parking lot of the old Rog and Scotty's Supermarket on West Broadway.
Ragland's friend, Matthew Gill, wielded the tire iron. Two other teens with Ragland and Gill also were charged in the assault.
Gill and the two other teens accepted plea bargains. Gill pleaded guilty to second-degree murder and was sentenced to 50 years in prison. He was paroled after three years.
Ragland went to trial and a jury found him guilty of first-degree murder. That brought the sentence of life in prison without the possibility of parole.
Ragland had filed numerous appeals, and all had been unsuccessful. The Iowa Supreme Court's decision said Ragland cannot appeal his conviction, but the sentence is another matter.
While the Fourth District Court and the Iowa Court of Appeals both denied his appeal, the Supreme Court ruled that the District Court must hear the cruel and unusual punishment challenge.
Pottawattamie County Attorney Matt Wilber said he is prepared to argue to uphold the sentence.
Wilber said that, in recent years, there has been a push nationwide by courts to rule on whether sentencing a juvenile to prison for life amounts to cruel and unusual punishment. But Wilber noted that most of those cases have not dealt with a homicide.
"The conviction has been ruled good, nothing is going to overturn that," Wilber said. "The question is (Ragland's) age at the time of the crime and the punishment."
Ragland's case has taken a number of turns over the years.
In 1997, he was one of six inmates who overpowered two private security guards at a Texas highway rest area while being transferred to a New Mexico prison. All six prisoners were recaptured a day later 100 miles north of the rest stop.
In 2002, Ragland told the Daily Nonpareil his escape was motivated by his desire to stay in an Iowa prison, close to his mother, who later died of cancer.
That same year, Council Bluffs attorney David Richter, who was the Pottawattamie County attorney at the time of Ragland's conviction, wrote a letter to then-Gov. Tom Vilsack asking him to pardon Ragland. Vilsack declined.
Wilber said the case is a prime example of his contention that first-degree murder cases "never go away."
"We have litigated this for the last 25 years and it continues," he said.
There has been no District Court date set to rehear Ragland's motion.