Johnny Lee Olds was born at his family’s home in Selma, Alabama. He was the youngest of 11 children, and he was and forever would be his mother’s baby.

Being part of a large family had its upsides. Olds had a built-in group of friends, which was especially helpful when his parents separated. His mother wanted a fresh start, so she moved him and his siblings to Pensacola, Florida, when Olds was about 5. A few years later, when Olds was 9 years old, he started hanging out with some older kids, many of whom were his cousins. They would often sit together in someone’s yard, and Olds would try to impress them by doing flips off cars.

During one of these outings around 1988, Olds and his friends noticed that a neighbor’s car was gone. They figured that meant the neighbor was also gone—and because his car was relatively nice, they also figured that he might have some money in his house.

“We needed some money, and we went and broke into one of the houses. Back then, a couple dollars was big to us,” Olds recounted. “We got away with it, so we kept doing it.”

But soon, the stealing caught up with Olds. Around 1989, Olds was placed in juvenile detention for grand theft auto. This became a pattern: Each time Olds was released, he would do something else—boost cars, mostly—and go right back in. 

“I’ve been incarcerated all my life,” Olds said. “Never stayed out over four months. From 9 all the way to right now.”

In 1994, when Olds was just 16 years old, he was transferred to a prison for adults. That facility was called Columbia Correctional Institution, and it was an eight- to 10-hour bus ride from his family. He was eventually transferred to yet another facility, which was even farther from his home. When he was released at the age of 19 in 1997, it took a full day to travel back to Pensacola by bus.

Olds knew that he wanted to stay out of prison this time, which meant he needed a job.

“I [was] working on the Pensacola docks, like unloading the ships and stuff, unloading the pallets and stuff coming in off the ships, and I worked in construction with my brother,” he said, but he knew working in the streets would pay more than a traditional job.

Around this time, Olds started a relationship with his child’s mother. While he wanted to settle down, the lack of employment opportunities led him back to the streets.

In September 2008, Olds sold a handgun at a pawn shop for $45. According to the plea agreement later entered in his case, Olds was selling the gun “for a relative because the relative did not have the required identification to conduct the pawn transaction/sale.” But Olds already had a few felony convictions by this point, which meant that he was prohibited by federal and state law from possessing a firearm—even if, in the government’s view, that possession lasted only the length of the pawn shop transaction.

State police initially picked up Olds, but then his case was transferred to federal prosecutors. They indicted him for being a felon in possession of a firearm in January 2009.

“In the state [system], I’m thinking the only thing I could get was five years at the most,” Olds said. But when federal prosecutors picked up his case, things changed. 

“When my public defender came to talk to me he said, ‘Man, you’re looking at anywhere from 10 years to 15 years.’ [Then] he’s telling me if I go to trial, nine out of 10 judges are gonna try to give me life; everything they can give me. So I said I’m just gonna take the 15 years [offered through a plea deal].” 

But when Olds went to court to enter his guilty plea in 2009, he says the judge balked. According to Olds, the judge talked about how she thought that he should go away for even longer than the government recommended.

“I’m so dumb to the federal system at the time,” Olds said. “I’m sitting there listening to [the judge], letting her talk this way to me.”

Olds acknowledges that, at the time, he was living “a messed up lifestyle,” but many of his choices at the time were influenced by the community he grew up in and the poverty he was navigating. “If I could go back in time right now—I regret everything I did when I was coming up,” he said.

When the judge informed Olds about the length of his sentence, he didn’t immediately understand how long it was because she read it in months.

“But when I added all the months up, when it said 17 [and a half] years, I just broke down in tears, man. I went back to the jail and looked at my kids’ pictures and started crying,” he said. At the time, Olds had a 6-year-old daughter, a 4-year-old son, and a daughter on the way.

These kinds of harsh sentences disproportionately affect Black men like Olds, who are imprisoned at five times the rate of white Americans. While Black people are only 12.5% of the U.S. population, they make up more than 50% of federal felon-in-possession cases.

And Black men like Olds are not only convicted and imprisoned disproportionately; they also go to prison for a disproportionately long time. In 2019, Black Americans constituted 46% of the prison population who had already served at least 10 years. The law’s reliance on criminal histories as a basis for determining prison sentences is a major driver of racial disparities in imprisonment, according to the research and advocacy group The Sentencing Project.

In the years since Olds’ 2009 sentencing, the law relevant to his case evolved. By 2019, it was clear that both his sentence and conviction were unlawful because courts reconsidered what type of criminal history should qualify people for longer sentences. This means Olds should not have been sent to prison for as long as he was. By this time, courts had also reconsidered what prosecutors needed to prove to convict someone for being in possession of a firearm if they were previously convicted of a felony, which also means that prosecutors may have lacked the proof necessary to convict Olds.

But in 2024, Olds has no path to relief from either his conviction or his sentence. 

The more things change, the more things stay the same

Who gets to benefit from changes in the law? It’s a question that has plagued U.S. courts for decades.

From time to time, courts reinterpret the Constitution and statutes. These new interpretations are sometimes more favorable to criminal defendants than prior interpretations. Courts must then decide who in the criminal legal system can benefit from these new interpretations. 

Consider, for example, the Supreme Court’s 1963 decision in Gideon v. Wainwright, in which a Florida man named Clarence Earl Gideon was charged with a felony. At trial, he asked that an attorney be appointed to represent him because he could not afford one himself, but the court denied his request. Gideon’s case eventually made its way to the U.S. Supreme Court, which held for the first time that the Constitution requires states to provide an attorney to indigent people charged with felonies.

The right to an attorney in criminal proceedings is now seen as a foundational constitutional guarantee. But when Gideon was decided, it was a revelation: the case interpreted the Constitution in the exact opposite way it had previously been understood. Before Gideon, states were not obligated to provide counsel to people who could not afford representation. After Gideon, they did.

When a ruling was issued for Gideon, many people who had been tried and convicted without an attorney were sitting in prison. Courts then faced the question: Should Gideon apply retroactively to them? In other words, did the courts have to release or retry all these incarcerated people because the current law suggested their trials were unconstitutional? Or should these people remain in prison because their trials were seen as perfectly constitutional at the time they occurred?

Courts ultimately decided to apply Gideon retroactively, and, according to the Journal of Criminal Law and Criminology, that decision brought about “re-trials and releases from prison unparalleled in American history.”  

Since Gideon, however, the federal courts have changed their approach. They are now much less likely to apply new rules to people who are already in prison. Supreme Court Justice Brett Kavanaugh has said that this stingy approach is designed “to mitigate the disruptive effects of overrulings in criminal cases.” In other words, courts do not want a repeat of the aftermath of Gideon. They don’t want to have to release or retry thousands of people each time they announce a new rule.  

The upshot of this current approach is that, even if a new rule confirms that someone is innocent, courts sometimes keep them in prison. That is essentially what happened to Olds.

No relief

When Olds was convicted and received his 17.5-year sentence, he knew he wanted to challenge it. When someone is in federal custody and wants to challenge their sentence or conviction, they have two basic options: First, file an appeal. This means the case then goes to a federal court of appeals and, on rare occasions, may continue to the U.S. Supreme Court. This process is called “direct review.” 

If a new rule is announced while the case is on direct review, the case usually benefits from it. But when direct review ends, the person’s conviction and sentence become final.

A person does still have a second way to challenge his conviction or sentence. That way is called post-conviction proceedings, or habeas corpus. This post-conviction process exists in part “to ensure that someone is not in jail for something that can’t be made criminal,” according to professor Amanda Tyler of Berkeley Law School.

“We are talking about incarcerating people and taking away the most fundamental of liberties—one’s freedom, one’s liberty in the truest, purest sense,” Tyler said. “At its core, habeas reflects the idea … that we want to get it right. We don’t want someone sitting in jail where their constitutional rights have been violated and those violations have contributed to the outcome that put them there. We need to be able to trust the process, and, because of the severity and the importance of what’s at stake, it is imperative to make sure that we should trust the process—that is, we need to ensure that it was fair and did not run roughshod over the Constitution in the race toward a conviction.”

Habeas review is more limited than direct review because courts want to give some deference to the direct-review process. For example, new rules generally do not apply in habeas proceedings, and in courts hearing habeas petitions, “a presumption of innocence has dissolved into a presumption of guilt,” says associate professor Jonathan Abel of University of California, San Francisco, Law. These limitations and others make habeas relief very hard to come by.

In 1996, however, Congress thought that securing habeas relief was still too easy and that federal courts were being overrun with “frivolous” habeas claims. Congress’ solution was to enact a new law called the Anti-Terrorism and Effective Death Penalty Act (AEDPA).

AEDPA imposed several new restrictions on habeas relief. For example, it required that incarcerated people seek habeas relief within one year of when their convictions become final, and it generally prohibited people from seeking habeas relief more than once. Additional requests for habeas relief are allowed only if they rely on newly discovered evidence or a new rule of constitutional law.

Most new rules from courts are not about constitutional law. In fact, courts are supposed to avoid ruling on constitutional questions whenever possible. But courts do regularly issue new rules that interpret statutory law—and sometimes those reinterpretations change our understanding of a criminal offense or how much prison time a person should get.

This is essentially what happened in Olds’ case.

Stuck again 

When Olds was sentenced in 2009, the judge thought the law required at least 15 years in prison. In a variety of circumstances, federal law requires judges to extend a person’s sentence because of his criminal history. In Olds’ case, the judge thought he was subject to a longer sentence because he had a certain number of prior “violent” felony convictions.

By 2016, however, that view seemed to be incorrect. A court held that some of Olds’ prior felony convictions were not actually “violent,” so they could not be used to subject him to a longer sentence. If he had not been subject to that longer sentence, then the law said he should have been sentenced to no more than 15 years.

“It’s sad because I know it didn’t have to be that way,” Olds said, reflecting on his sentence. “Because I see other people get caught with all kinds of guns, and they don’t get no five or six years. I get caught with one gun, and it wasn’t even in my possession, and I get 17.5 years.”

In 2019, the law evolved yet again in a way that impacted Olds. This time, it was his conviction—rather than his sentence—that proved to be on shaky footing.

To convict someone of a crime, the government must prove each element of a defendant’s alleged crime beyond a reasonable doubt. If the government fails to prove an element, it has failed to prove the defendant’s guilt. In the eyes of the law, the person is innocent.

For decades, courts held that to convict someone of being a felon in possession of a firearm, the government did not need to prove that the defendant knew they were a felon. In 2019, however, the Supreme Court held in a case called Rehaif v. United States that the government did have to prove a person’s knowledge of their felon status to convict them of this crime.

When Rehaif was decided, almost everyone who was in prison for being a felon in possession had been convicted without that proof. Many incarcerated people quickly moved to vacate their convictions, arguing that because the government failed to prove an element of their offense, they were innocent in the eyes of the law and should be released.

According to AEDPA, however, Olds cannot seek relief from his now-unlawful conviction or sentence.

Olds had filed a motion for habeas relief in 2014 before any of these changes in the law occurred. That motion was unsuccessful. 

Although Olds wanted to file another motion for habeas relief after the recent changes in the law, AEDPA only allows someone to file a second motion for habeas relief if that second motion relies on newly discovered evidence or a new rule of constitutional law—neither of which helps Olds.

If Olds attempted to file a new motion for habeas relief based on Rehaif, that motion would fail because Rehaif did not interpret the Constitution—it interpreted only a federal criminal statute. Similarly, if Olds sought relief from his sentence, that motion would fail because it would rely only on recent court decisions interpreting a federal sentencing statute, not the Constitution. Everywhere he turns for post-conviction relief, Olds faces another closed door.

Olds said that the way the federal judge in his case talked to him “really messed my head up at the time, and I really ain’t recovered from that because I’m still suffering from something I know I could have gotten less time for. She took me away from my family for 17.5 years … She knew all my kids were young at the time. All of them were babies,” he said.

The Supreme Court doubles down

Another law—called Section 2241—could prevent unjust outcomes in cases like Olds’. Section 2241 says that anyone who claims to be unlawfully detained can seek habeas relief, and AEDPA says that a person can seek habeas relief under Section 2241 if the remedy in AEDPA is inadequate.

For decades, most courts agreed that Section 2241 created a path for people in Olds’ position to seek habeas relief. But in 2023, in a case called Jones v. Hendrix, the Supreme Court rejected this view of the law—leaving Olds, again, stuck in prison.

As a leading law school textbook explains, “Jones v. Hendrix marks yet another Supreme Court decision in recent Terms scaling back opportunities for post-conviction review while elevating the principle of finality [of criminal convictions and sentences]. It is, in this respect, in considerable tension with decisions from only a few terms prior.”

“This time around in prison I feel like, shoot, I really can’t describe it, but it was hell being away from my family,” Olds said. “And I feel like it was for no reason … [because] I could have gotten less time for it. I could have got no time at all.”

After years in prison, Olds was released to a halfway house May 8—allowing him to finally reconnect with his children, who are now fully grown. But he’ll never get over how unjust the system is and how much of his life he lost to it.

“I feel like I’ve been mistreated, and [the justice system] took half of my life away from me,” Olds said. “I look at it [like] they just took the shackles off [our] legs and put them on our brains. That’s all there is to it.”

Editor’s note: Kendall Turner knew Johnny Lee Olds prior to writing this piece and for a time helped with his case.