Albert Woodfox once told a friend after languishing for decades in isolation that he would not be broken — but friends and supporters worry about the toll it has taken on his mind and body.

The 68-year-old Woodfox is the last member of the "Angola Three" still locked up in a case that has highlighted the use of solitary confinement in U.S. prisons.

"Realistically, I thought Fox was dead," said Parnell Herbert, a 66-year-old New Orleans playwright and boyhood friend of Woodfox, describing his thoughts after learning in 2001 of his friend's solitary confinement. But Woodfox told Herbert, "They will never break me."

Woodfox's case took a dramatic turn Monday when a judge ordered his immediate release and barred the state from seeking his retrial on charges that he murdered a prison guard in 1972.

But the state is appealing the ruling and on Tuesday won an emergency stay of his immediate release, meaning he is likely to remain in jail until at least Friday.

Woodfox was part of a group of three men who came to be known as the "Angola Three" for their extensive stays in solitary confinements at the Louisiana State Penitentiary, a state prison farm and former slave plantation located in Angola, Louisiana.

One of the three, Herman Wallace, died in October 2013, days after a judge freed him and granted him a new trial. The third, Robert King, was released in 2001 after the reversal of his conviction in the death of a fellow inmate in 1973.

Woodfox is the last left.

He's long maintained his innocence in the guard's killing, which happened during protests of brutal conditions inside the huge penitentiary. His two previous convictions were overturned for possible racial prejudice, and the state is currently trying to try him a third time.

Woodfox was put in solitary confinement after being accused of the guard's murder, but his supporters say it was retribution for his Black Panther Party activism to protest prison conditions.

The federal judge who ordered his release Monday said the state can't fairly try Woodfox a third time for the prison guard's slaying, and that the "only just remedy" would be setting him free after all the years he spent in "extended lockdown."

The use of solitary confinement in his case has drawn international condemnation by supporters. They describe the conditions under which Woodfox has been held as inhumane and a form of torture.

Most of the time was spent at Angola, where he was generally denied contact with the general prison population and kept in a roughly 55-square-foot cell 23 hours a day, his supporters say.

The isolation continued when he was moved to another state prison in 2010.

An attorney for Woodfox, George Kendall, described the conditions Woodfox has served his time under as "brutal," and blasted the attorney general for fighting to keep him incarcerated.

"This case ought to end," he said.

But state authorities contend his situation is not that harsh. They say he has been allowed visitors and reading material, and can see a television and communicate with others, including other inmates and chaplains, through the bars of his cell. And they've pointed repeatedly to the severity of the crime he's accused of.

"The perception of 'solitary confinement' is a far cry from the reality," said Aaron Sadler, a spokesman for the Attorney General's office.

Many of his supporters have followed the case intensely.

Angela Allen-Bell, an assistant professor of legal writing and analysis at Southern University Law Center in Baton Rouge, said she speaks with Woodfox regularly by telephone and visits him about once a month.

Speaking of the judge's Monday ruling, she said: "I read the order line by line and cried when I read it."

She described a litany of health issues that she blames on his isolation, including panic attacks. And she said he suffers from health problems such as diabetes that have been exacerbated by the solitary confinement.

"He does not allow himself to be very optimistic about things. I think that that is a coping mechanism that he has developed. But we talk often about the power of prayer and the ability of God to deliver miracles. And I do believe that he believes that that is possible," Allen-Bell said.

The "Angola Three" were all active in hunger strikes and work stoppages that spurred improvements to prison conditions, and all three suffered harsh treatment thereafter as prison authorities kept them isolated at Angola to prevent more disruption behind bars.

Herbert said that at one point, the Angola Three refused to submit to dehumanizing cavity searches for contraband. He said they were then taken to a chamber where prison guards beat them with clubs and baseball bats — but they eventually won a battle in court to end the searches.

In ruling against a third trial, Brady cited the inmate's age and poor health; the unavailability of witnesses; "the prejudice done onto Mr. Woodfox by spending over forty years in solitary confinement"; and "the very fact that Mr. Woodfox has already been tried twice" before his convictions were overturned.

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Associated Press writers Rebecca Santana in New Orleans and Brian Slodysko in St. Francisville contributed to this report.