At one point Los Angeles County District Attorney George Gascon's Office told the court they would not oppose Scott Breckenridge's petition for release after he served 30 years of a 73-year sentence.
Prosecutors later said they had misinterpreted a new office policy and they no longer support Breckenridge's release.
On Wednesday, Breckenridge still made his case to a judge to become a free man, as one of his victims listened to the proceedings by telephone.
It has been 30 years since Breckenridge raped the woman, identified only as Lori R. She was on her way to a bus stop in January 1991 when Breckenridge forced her into a stairwell and raped her.
"This is something that stays with me, especially in the darkness of the morning when the time changes because that's when my incident happened, around 6-6:30 in the morning," Lori R. told the court via telephone.
"That's a fear that stays with you."
Breckenridge was found guilty later that year, on nine counts involving several victims.
Over the summer, the DA's Office said it would not oppose the defendant's request for a shorter sentence, which would have helped clear the way for Breckenridge to walk free.
That changed on Sept. 7, when the deputy district attorney on this case said the team misinterpreted Gascon's resentencing policy, and that they no longer support Breckenridge's release.
Since taking office last December, Gascon has issued sweeping changes to how his office handles cases, some of them generating controversy for potentially leading to reduced sentences and early releases.
LA County DA George Gascon's sentencing policies questioned by crime victims' families
LA County DA George Gascon's policies on sentencing spark controversy
Still, Breckenridge took his opportunity to speak up about something he says happened to him in 1985, while he was serving in the U.S. Army.
He told the court he, too, was raped, by a sergeant.
"I realized that he put something in my drink, because I woke up maybe nine or 10 o'clock that night, and he was on top of me," said Breckenridge. "I was on my stomach and he was sodomizing me."
That, his attorney said, contributed to PTSD.
What it did not do, for Judge Terry Bork, was show cause or excuse Breckenridge's behavior in the years after.
Judge Bork denied the petition, saying the factors that led to Breckenridge's original sentence still hold true today.
Lori R. told the court: "When I watch (shows involving rape) on TV, when I hear it on the street, on the news or anything like that, that fills a total mental hatred inside of me because of people like him."