Aaron, seen here at his mother’s home in Mobile, Ala., was released from prison in 2014 after 22 years. His life, he says, is still in a state of transition
Radcliffe Roye for Time
By Maya Rhodan
October 27, 2016

Before Clarence Aaron was sentenced to life in prison for charges related to crack cocaine, he was a 23-year-old linebacker at Southern University at Baton Rouge. Strapped for cash, he decided to make extra money by introducing two sets of friends who were both in the drug business. For this, Aaron was paid $1,500. He never got involved with weapons or violence, and he says he never handled the drugs himself. But each of his co-conspirators testified against him, pinning 24 kg–more than 50 lb.–of cocaine on the former Boy Scout. Federal sentencing guidelines for drugs were extremely harsh in the 1990s, and Aaron was sentenced to three concurrent life sentences, far more time than anyone else involved.

“Prison is a very gloomy, bad place. In order for you to survive in there, you have to elevate above the situation that you’re in,” he says. “The first thing I did was get a job.” He took classes in economics and religion, earned a computer-programming certification and eventually served in the highest inmate-occupied position in the prison’s textile factory. When he was transferred to a lower-security facility in Alabama, he was a leader in a prison factory that produces uniforms for the U.S. military.

Aaron was supposed to die in prison, but a decision by President Obama made it so that he did not have to. On Dec. 19, 2013, Aaron and seven other nonviolent drug offenders found out their sentences were commuted. For the Obama Administration, Aaron’s case was a clear example of the human cost of the harsh laws of the war-on-drugs era, particularly for citizens of color. Obama has since shortened the sentences of 774 prisoners, more than the past 10 Presidents combined, and pushed for legislation that would reduce the prison population by 17,000 between 2017 and 2021. The moves were intended to close a chapter of American history that overcrowded prisons and tattered the social fabric of urban communities. But for the individuals, release into society is one step, albeit a big one, in a lengthy struggle to readjust.

Last spring Attorney General Loretta Lynch visited Mobile, Ala., where Aaron now lives, to discuss the challenges of re-entry. She invited the former inmate, now 47, to offer the perspective of former prisoners. Aaron related a story of hope hedged with continued hardships. Just getting out, he said, wasn’t a silver bullet. Returning citizens need jobs, he said. “I’m not asking nobody to give me nothing. I want to earn everything I get,” Aaron said, leaning on the wooden lectern for support. “It’s just about an opportunity.”

Aaron had been working 14 hours a day, six days a week, at a restaurant owned by a friend. He has since cut that in half so he’ll have more time to focus on finding something better. He’s applied for a handful of jobs but has yet to hear back on any of them. “I don’t know if it’s that people look at you as incarcerated, convicted felon or what,” he says. “I’m just having an issue with that right now. It’s a continued uphill fight.”

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Three years on, life is a mixed bag for the low-level nonviolent drug offenders Obama freed at the start of his second term. TIME spoke to six of the original eight over the course of the summer–one didn’t wish to be included, and another could not be reached–to get a sense of what is in store for the hundreds of others who have the President to thank for their release. After decades of being away, two live on their own, two live with partners and two live with parents. Their median age is 46. Reconnecting with family was easy for some. For others, children still struggle with having an absent parent back at home.

Most juggle part-time work to make ends meet, but breaking out of low-wage jobs has not been easy. Yet for all the challenges, spirits are high. Life outside prison definitely beats the alternative. They keep in touch, not just with each other but also with friends they met behind bars. Through Facebook groups and email chains conversations happen among like-minded folks whose circumstances can be fully understood only by others who have experienced them.

That’s actually a lot of people. Each year, about 600,000 prisoners are released from state and federal prisons. At the federal level, only about 2.5% of current prisoners are locked up for life, meaning nearly every person behind bars right now will eventually get out. For returning citizens, some challenges are all too apparent–landlords who won’t rent to former felons, schedule restrictions placed by parole officers. But others are more subtle, and in many ways more difficult to address.

After decades behind bars, everyday behaviors that others learn without even realizing it–like ordering at a fast-food joint or figuring out how to work a TV remote–can prove challenging. Family dynamics change. Some relatives have passed away. Others harbor guilt toward their incarcerated moms, dads, brothers, sons, daughters. And many former prisoners say they live in constant fear that their past incarceration–the third or more of their lives lived under federal supervision–is obvious to every casual observer. “There’s so much catching up to do when people have spent decades behind bars, and then somehow we expect them to assimilate,” says Julie Stewart of Families Against Mandatory Minimums, a Washington-based organization that has advocated for executive clemency.

For some, that adjustment proves too difficult. A recent U.S. Sentencing Commission study found that almost half of the federal prisoners released in 2005 were rearrested after eight years, and a quarter ended up back behind bars. But in some ways demography really may be destiny, and crime remains largely a young person’s game. The longer you’re behind bars and the older you are at sentencing and release, the less likely you are to go back. Another Sentencing Commission report–focused solely on crack-cocaine offenders who were released early–found that those offenders were no more likely to recidivate than other prisoners. There are barriers for returning citizens of all ages in the free world too, known as “collateral consequences.” These are the rules that bar former offenders from obtaining professional licenses and securing housing and, in some cases, food benefits. For someone convicted of a drug offense, there are at least 50 federal collateral consequences, according to an American Bar Association database, though they vary by state. For example, Alabama, where Aaron lives, bars former prisoners from working or volunteering in child care or at an adult-care facility, and it can be difficult for former prisoners to obtain an athletic-training license. “People do find jobs–it’s not as if they don’t work,” says Steven Raphael, a public-policy professor at the University of California, Berkeley. “It’s more an issue of how the opportunity set that they’re selecting from is shaped.”

The Obama Administration has taken steps to address barriers to re-entry. “Right now the deck is stacked against people being able to successfully stay out,” says White House senior adviser Valerie Jarrett. “So while they’re in prison let’s give them the tools that they need, and when they’re released from prison let’s ensure that we give them a job, that they have a place they can live.” Last spring the Administration made obtaining an ID easier for former prisoners, expanded their medical coverage and banned questions about arrest histories on preliminary applications for federal jobs.

At the start of Obama’s final year in office, there was hope that federal criminal-justice reform would finally pass Congress. The proposed bills would make retroactive the 2010 reductions to federal sentencing guidelines on crack cocaine, reduce mandatory-minimum sentences for low-level drug crimes and remove some barriers to re-entry. But momentum has slowed. Donald Trump cast himself as the “law and order” presidential candidate as violent crime ticked upward in some major cities. House Speaker Paul Ryan has signaled interest in carrying criminal-justice reform over the finish line in the lame-duck session, but he could face an obstacle in the form of Senate majority leader Mitch McConnell.

Because Helen Alexander Gray lives in a small town, everywhere she turns, someone recognizes her as the woman who went to prison. “They don’t come up directly to me,” she said in a phone call from her hometown of Ty Ty, Ga. (pop. 727), about 90 miles north of Tallahassee, Fla. “They will say, ‘That lady right there, she went to federal prison.’ I hear them, but I pretend I don’t.”

Gray was a 40-year-old homeowner when her boyfriend’s drug dealing landed her with a 20-year prison sentence in 1996. She claims she never actively sold or did drugs, but when her boyfriend and his co-conspirator went down for crack cocaine, she did too. Gray held a job her entire time behind bars and ultimately earned a commercial driver’s license. Because she was freed early, Gray celebrated her 60th birthday with family and friends in late July. She counts herself fortunate to have a house waiting for her–even though the floors were rotting out and her closets of clothes reeked of mildew and decay. “I don’t know what I’d do about paying rent,” she says.

The size of Ty Ty has made her job hunt difficult. The places that typically hire former inmates, she says, are miles away. Working in a hospital or driving a school bus are out of the question. Likewise, working for a courier service; lifting boxes would strain her back. “It’s very hard for a person like me in a small town to get a good job,” she says. “I had a decent education when I went to prison. I had good jobs when I went to prison. But when I came back, with those same skills, I haven’t had the same opportunity.” For now, Gray drives tractor trailers with a childhood friend when he has extra work, but that’s about it. She relies on her two sons, ages 35 and 38, for help with bills.

To keep her spirits up, Gray keeps in contact with a group of women she bonded with in prison, each of whom are experiencing different iterations of the same story. Their bond is more familiar than friendly, she says. Sometimes, on the phone, they revel over no longer being behind bars. Other times, they swap stories about their challenges via email. “Prison is not an easy ride, can’t nobody describe prison to you until you go there and stand in those shoes,” Gray says. The same can be said for re-entry.

Jason Hernandez still wakes up at 5:30 every morning, not far from the time he’d rise for breakfast in the prison mess hall at FCI El Reno. But now he controls what he eats for his first square meal of the day, and his mother is often the cook. When he was younger, he was a well-known drug dealer in McKinney, Texas, learning the ropes from his brother J.J., who introduced him to the streets at age 15. When J.J.’s drug dealing and addiction landed him behind bars, Hernandez took the reins, supplying marijuana and eventually dealing cocaine and crack. By age 21, Hernandez had joined his brother in prison with a life sentence and no possibility of parole, leaving behind a young son. Life, he says, was like that in Groundhog Day: every day was more or less the same.

These days Hernandez lives with his parents, and life is flexible as well as routine. This summer, at age 41, he graduated from high school. He works part time as a welder, a skill he picked up in prison. He got the position because he took his clemency letter to job interviews as a reference. After all, who would turn down a guy the President vouched for? The bulk of his free time is spent on advocacy work. He works with activist organizations and colleges on prison-related projects and is a youth-outreach coordinator for a Texas-based substance-abuse recovery program.

When Hernandez was locked up, he and his brother launched a website called Crack Open the Door aimed at helping other nonviolent lifers seek justice. A few of the prisoners profiled on his site have already received executive clemency. But the names of others whose stories mirror his he recites from memory: Michael Holmes, Altonio O’Shea Douglas and Eva Palma Atencio. His work has paid off. Recently, Obama commuted the sentence of Josephine Ledezma, for whom Hernandez filed the petition for clemency.

For now, Hernandez says, his social life is nonexistent and dating is out of the question. “I can’t get into a relationship and have another kid,” he says. “I can’t give dedication to family and work.” Plus, how would he introduce himself and his life’s work without having to explain how and why he became a criminal-justice crusader? He goes through a sample icebreaker over the phone, in which he introduces himself and is subsequently asked what he does for a living. Bam, right into a discussion about how he spent 17 years in prison. “Whoa, who’d you kill?” is a response he’s gotten before. But as much as he considers his status as a formerly incarcerated person a black mark, he doesn’t want to lose sight of it. “No matter what I do, I’m an ex-felon,” Hernandez says. “But that’s O.K. That’s what drives me. I don’t want to forget that.”

There’s a peculiar feeling ex-prisoners get when they move freely about society, a tinge of anxiety many say they’ve felt walking down the street or driving home from the store. When Billy Ray Wheelock walks down a street, he is often aware of the people approaching behind him, a habit he picked up after two decades behind bars. But Wheelock, who was convicted of intending to distribute 50 g of crack, doesn’t live with regret. “It’s been over two years now. I haven’t had one bad day,” says Wheelock, who celebrated his 2014 release from a federal halfway house by getting married to a woman, Berna, he met online while in prison. “I’d seen my hell for 21 years. Every day I’m in heaven.”

That’s not to say Wheelock’s life is without challenges. Earlier this year Berna was diagnosed with colon cancer. Her illness left her unable to work, leaving Wheelock, 53, as the primary breadwinner. (She recently had her last chemotherapy session.) Wheelock takes great pride in the work he does as a line cook and dishwasher in chain hotels and as an HVAC repairman around Denver. For a while, he says, he was so popular at his temp agency that he was in “high demand.” Now he’s working full time as a cook at a local volleyball club and supervising other HVAC repairmen. He also works part time doing security at Denver Broncos games and other sporting events. And he’s writing a book, titled Faith Without a Date, about his time behind bars and his belief that he would be released despite having been sentenced to life. “I’m not Mr. Perfect,” he says. “I’m still trying to adjust to freedom and to life, but what defines you at the end of the day is your ability to keep moving forward.”

When prisoners spend years behind bars, a lot changes. Technology evolves. Fashion shifts. Babies are born, and family members die. Hernandez’s brother was killed in a Texas prison in 2002. He says that death awakened him to the dangers of conforming too much to life inside prison. Weeks before receiving the news of her commutation, Stephanie Yvette George was informed that her youngest son had been shot and killed. His death has complicated her efforts to rekindle her relationship with her surviving children. Soon after her release, she called her kids to arrange outings for lunch or dinner, but neither her son nor her daughter ever seemed to be free on the same day. When she finally confronted them about it, they said that when the three of them are together, the loss of their little brother, who was just 20, stings more.

“When they’re around me, it brings back memories of him not being here with us,” George says from her home in Pensacola, Fla. “It’s getting better. It’s not something that we can get over, but we’re going to get through it.” When George was younger, drug dealers were her type–men who would support her financially as long as she helped them sell drugs. When she was 23, she was put on probation after being caught on a porch next to a bag of drugs and confessing to arresting officers that she was carrying crack. Three years later, thanks to the help of confidential informants keeping tabs on her, police raided her home and found drugs, cash and paraphernalia. At age 26, she was sentenced to life in prison.

Her transition since being released hasn’t been easy, but things are looking up for George. She was recently brought on as a full-time employee at a Hitachi Cable America, where she works on an assembly line building brake lines. The work is faster-paced than her previous job as a server at a buffet restaurant, where she worked only about 24 hours a week for $8.47 an hour. Now she works 10 hours a day for $10 an hour and is eligible for overtime, health benefits and a 401(k). After sending out as many job applications as she could, George seems to be inching toward what she has craved since her release. Although she still pays $5 a month to pay off a $3,000 loan she took out for beauty school before prison, she’s doing O.K. “I’m comfortable paying my bills,” George says. Compared with where she was, “I’m not really stressing.”

For all the difficulties each of the former prisoners we spoke to have faced outside prison, they don’t make a habit of complaining, knowing the alternative as well as they do. But while Aaron and Gray are still waiting for an opportunity to demonstrate their full potential in society, Reynolds Wintersmith got his chance not long after his release.

As a teen, Wintersmith worked for two weeks in a job in his hometown just outside of Chicago. He hoped to use the money to assist himself and his siblings, who’d been left to fend for themselves after their mother overdosed on drugs and their grandmother was sent to prison for cocaine trafficking. But the first check Wintersmith brought home was for $75, not enough to take care of his family. So he quit and sought out work on the streets. He sold drugs, got involved with a gang and soon joined its top ranks. At age 19, Wintersmith was sentenced to life in prison. When he was on trial, he realized he needed to take control of his life. He earned his GED before his first official day in prison.

His whole mind-set changed, Wintersmith says. He wanted to become a better person, and wasted no time doing it. When he was released at age 39, he took the same approach, using the skills he’d learned in prison to find a job working for a fashion designer in Chicago, a woman he met after she put on a fashion show at his halfway house during Black History Month. They bonded because she had a son in prison, also convicted of a drug crime, and the only way her son would be released from prison was via executive clemency. The sight of Wintersmith, free after being destined to die behind bars, gave her hope.

From there, Wintersmith networked in search of more meaningful work. He’s now a counselor at a charter school on the city’s West Side, helping disaffected youth stay on the right track. “When I was incarcerated, I never stopped believing that I was going to get out of prison,” he says. “I would die in a prison cell before I stopped believing that I was going to get out of one.”

The drive he brought to redefining his life, both inside and outside prison, serves as a lesson in the importance of self-control, he says. Early on a summer evening, as a community-college semester drew to a close, Wintersmith observed that life outside is not so different from life inside. “There’s many more distractions, there’s a lot more freedoms that you didn’t have in prison,” he allowed. “But fundamentally, for me, it’s the same.”

Besides freedom, attitude is what the first people freed by Obama have in common. There is a hopefulness underlying their post-release woes, a quality that may ease the way for those coming behind them.

Back in Alabama, Clarence Aaron has yet to hear back on all the jobs he applied for. But he’s still not complaining. The longer a person is out of prison, the less important their criminal history becomes, especially if their crime was nonviolent. “My transition has been a joyful one, even though it’s a work in progress,” he says. “I’m at a crossroads. I know that I’ve done what I’m supposed to do, but is there more that I can do?”

This appears in the November 07, 2016 issue of TIME.

Contact us at editors@time.com.

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