Life outside the Lovelock Correctional Facility, a medium security prison in Nevada's high desert, could well resemble Simpson's solitary years after he was acquitted in the slayings of his ex-wife, Nicole Brown Simpson, and her friend Ron Goldman, CNN legal analyst Jeffrey Toobin said Thursday.
"I think it will be a lot like life was between 1995 and 2007," Toobin said. "He was really a pariah. His old life was gone -- celebrity pitchman, sportscaster, actor, all gone."
So what's next for the 70-year-old who was known as the "Juice" during his football heyday?
The next chapter in Simpson's life could begin as soon as October, the earliest he could be released, according to David Smith, a spokesman for the Nevada Board of Parole Commissioners. The state must now develop his release plan.
What will Simpson do?
One option for Simpson, Toobin said, would be to return to a life of memorabilia sales and autograph signings.
"I think it will be a pretty seedy existence," Toobin said. "He'll be trying to make money off what's left of his fame. It's mostly infamy, not fame."
Simpson's involvement in the world of memorabilia sales was what got him a nine-to-33-year sentence for his role in a 2007 incident that unfolded in a Las Vegas hotel room.
Simpson and armed associates allegedly confronted two memorabilia dealers and took pieces of memorabilia from them.
The "Juice" was convicted on charges including kidnapping, armed robbery and assault with a deadly weapon.
The former college and pro football star said at his sentencing that he was trying to reclaim family heirlooms and other personal items that had been stolen from him, and claimed he was unaware his associates were carrying guns.
What skills has Simpson gained behind bars?
At his parole hearing Thursday, Simpson said that he is a Baptist, and that a few other inmates asked him to help create Lovelock's first Baptist service.
"I worked with them," he said. "We now have an ongoing Baptist service that ... is well attended. I attend it religiously, and pun is intended."
"I was always a good guy but could have been a better Christian and my commitment to change is to be a better Christian," he added.
Simpson also said he recently became commissioner of the 18-team softball league.
"My primary responsibility was rules enforcement and, you know, player comportment," he said, adding that he decided on removing players from games and suspensions.
"I never got any blowback from the guys because they know how to act. I've done the best I can and just trying to keep them out of trouble. So my agenda was full here. I've been active, totally active for as long ... I've been here. I don't have much time to sit around and do anything."
He also completed a number of courses, he said, including one entitled "Alternative to Violence."
"I think it's the most important course anybody in this prison can take, because it teaches you how to deal with conflict, through conversation," Simpson said.
"I have been asked many, many times here to mediate conflicts between individuals and groups," he said. "And it gave me so many tools on how to use it, that you ... try to walk these guys through. Not throwing punches at one another."
O.J. Simpson, the webcaster and blogger?
Simpson said he completed a computer course that has helped him stay in touch with his four children.
"I took a computer course here not because I was computer illiterate, but I took the computer course because ... sometimes I could never get my kids on the phone," he said. "But if you text them or send something to them on the computer you can get them."
In June 1967, Simpson, then 19 years old, married his 18-year-old high school sweetheart, Marguerite Whitley. The couple had three children, Arnelle, Jason and Aaren. Aaren drowned in the family swimming pool just before her second birthday in 1979.
At his parole hearing, Arnelle Simpson, O.J. Simpson's oldest daughter, said her father was "my best friend and my rock."
Simpson lamented to the parole board that he had missed too many graduations and birthdays. He's anxious to get back to family and friends.
"I've done my time," he told the board. "I would just like to get back to my family and friends, and believe it or not, I do have some real friends."
Simpson and Brown married in 1985 and had two children, daughter Sydney and son Justin.
In a letter to a friend -- which was read in court -- Simpson wrote, "Who knows, you may even see a webcast/blog in my future."
Simpson urged the friend, Ozzie Fumo, now a Nevada state legislator, to support prisoner education.
"It wasn't until I got to prison that I realized just how many people did not have the exposure to ... education -- in part because of their circumstances i.e. gangs, bad neighborhoods, lack of parental supervision, poverty, etc.," Simpson wrote.
How much is Simpson's NFL pension worth?
Simpson stands to do better than most who have just been released from prison.
The NFL won't say how much he'll get from his NFL pension,
and it's hard to estimate without knowing some key details, such as when he decided to start collecting benefits. But according to the NFL benefits formula, if Simpson waited until age 65 to start drawing his pension, he could receive as much as $100,680 a year, and could have amassed more than $500,000 during the time he was in prison.
If he started at age 55, he would have accumulated $566,000 in benefits up until now, but he'd only get about $47,000 a year going forward.
Simpson also reportedly has made $5 million in contributions to a retirement plan run by the Screen Actor's Guild, according to USA Today.
Were the Goldman and Brown families compensated?
Simpson was found liable in a 1996 civil trial for the deaths of Goldman and Brown-Simpson, and was ordered to pay $33.5 million in damages -- more money than he had. Most of that money has not been collected.
He moved to Florida, where state law prevented his pension and home from being seized to pay the damages. Simpson's Heisman Trophy was ordered sold and brought in $230,000.
Where will Simpson go?
Simpson told the parole panel that he will likely return to Florida.
"I could stay in Nevada but I don't think you guys want me here," he joked.
The Nevada Division of Parole and Probation will investigate Simpson's proposed release plan.
Michelle Glady, a spokeswoman for the Florida Department of Corrections, said in a statement that if Nevada's relocation request for Simpson "meets all criteria, Florida must accept the transfer."
Fumo, the lawyer and Nevada state legislator, told CNN affiliate KLAS-TV
that the former running back is "looking forward to the future."
"He's a better person than what a lot of people, you know, think he is," Fumo said.
"He's not going to be golfing everyday. I think the physical part has really taken a toll on his life."
Toobin predicted Simpson's eventual return to Florida, where bankruptcy laws will enable him to protect his assets from the Goldman family. Toobin also predicted that Simpson will likely continue to surround himself with seedy figures from the memorabilia world.
"It's a far cry from the old life in Brentwood, but it's a hell of a lot better than being in Lovelock prison," he said.
Simpson will likely make money selling interviews and memorabilia, Toobin said.
"He is a deeply delusional and self-obsessed narcissist, and, you know, good luck to America once he's out," he said.