Reynolds Wintersmith, left, and Serena Nunn share their stories at a briefing on Capitol Hill in May to urge members of Congress to support sentencing reform. [Photo by John Kuhn, Social Justice News Nexus)

Reynolds Wintersmith had been asked the question before, by prison guards and other inmates. He had even asked it of himself. But one morning last May, as the Chicago man sat wearing a charcoal suit in a jam-packed room on Capitol Hill, Wintersmith was asked the question for the first time in front of people who have the power to change the answer.

“How much time do you think that you needed in prison?”

Wintersmith knew, of course, how much time he had gotten. In 1994, when he was convicted at age 20 for selling crack, a federal judge had sentenced him to life plus 40 years. He served more than 20 years of that sentence before President Obama commuted it in December, making him one of only 10 commutations the president has granted out of more than 14,000 requests.

Wintersmith’s answer to the question posed to him during that May briefing in Washington?

He struggled. “It’s impossible for me to measure how much of my liberty should have been taken away,” he said.

His freedom comes just as the nation itself grapples with the question of how to rethink the decades-long war on drugs. Swelling prison populations, ballooning federal budgets and new research on the impact of mass incarceration have garnered bipartisan support for reforms within the criminal justice system.

Since 1970, the U.S. prison population has quadrupled. In a 2014 report, the National Research Council found that roughly 1 out of every 100 adults are in prison or jail, which puts the U.S. rate of incarceration up to 10 times higher than that in Western European countries and other democracies.

The situation in Illinois isn’t much better. The state prison population has increased roughly 9 percent over the past seven years, said Tom Shaer, director of communications for the Illinois Department of Corrections. With just under 49,000 people now serving time, IDOC is operating close to its 50,523-inmate capacity. “Crowded? Yes. But not overcrowded,” Shaer said.

That may not be true for long. Projections from an April 2014 IDOC quarterly report predict that next March the inmate population will surpass 50,000.

In 2012, the Government Accountability Office reported that federal prisons were operating at 38 percent over capacity. In 2010, the U.S. spent roughly $80 billion on corrections, or about $260 per U.S. resident.

Three proposals are currently offered for federal prison reform.

First, and most comprehensive, is the Smarter Sentencing Act, a bill introduced by Sen. Dick Durbin, D-Ill. It would cut mandatory minimums in half and allow about 9,000 prisoners a chance to return to court for re-sentencing consistent with today’s sentencing guidelines.

Wintersmith, for example, was convicted at a time when crack counted 100 times more than cocaine in terms of sentencing, even though the two are the same base product. The 2010 Fair Sentencing Act drastically reduced the penalty for crack possession, but it didn’t apply to people already locked up. The Smarter Sentencing Act would make the Fair Sentencing Act retroactive along with slashing mandatory minimums.

This proposed legislation continues to draw co-sponsors from both sides of the aisle – 32 in the Senate and 50 in the House. When Tea Party favorite Sen. Ted Cruz, R-Texas, signed on to support the legislation this year, Durbin joked that he thought to himself, “I’d better re-read this bill right now.”

The bill passed out of the Senate Judiciary Committee but has not yet been called for a full vote.

Second, in April the U.S. Sentencing Commission voted to adapt guidelines that federal judges use to determine prison terms so the quantity of drugs that offenders possess at the time of their arrest will count less in the convoluted sentencing formula used to decide sentence length.

And last month, the commission voted unanimously to apply the new guidelines to those already in prison. This could mean an average sentence reduction of more than 20 months for nearly 50,000 prisoners. Unless Congress rejects the proposals, the new guidelines will be implemented in November. Sentences would not be eligible for reduction until November 2015, however, to give judges and prosecutors time to process the changes.

Third, an initiative within the Justice Department would revamp the clemency application process, making it easier for inmates like Wintersmith to be identified and granted commutations if their cases warrant.

However, as talk of change makes headlines, opposition has bubbled up.

Nearly 30 former top Justice Department and Drug Enforcement Agency officials wrote a letter in May to Senate leaders urging them to kill the Smarter Sentencing Act, arguing that the reason the U.S. has seen a drop in crime over the past three decades is because of severe penalties for drug offenders.

Disagreement among top-level officials and lawmakers only crystallizes the difficulty of sentencing offenders in a manner that’s perceived as fair, not just for prisoners, but also for communities across America.

Race and the war on drugs

Throughout the 1980s and early ‘90s, crack reigned in inner-city environments while cocaine ran through suburbs and more affluent – majority white – communities, intensifying an already stark divide. Neighborhoods in America most torn apart by the effects of crack were black neighborhoods in big cities.

Black men between the ages of 26 and 34 were more likely to use crack than people of any other racial and gender combination. According to a 2013 study by the National Forum Journal of Counseling and Addiction, 85 percent of offenders arrested in the last three decades for crack cocaine were black.

Research published by economics professors at the University of Chicago in 2006 shows that between 1984 and 1994, when crack use exploded, the homicide rate for black males between the ages of 14 and 24 nearly doubled.

“During this period, the black community also experienced an increase in fetal death rates, low birth-weight babies, weapons arrests, and the number of children in foster care,” wrote authors Steven Levitt and Kevin Murphy.

The reality of these numbers gripped many communities across the country with fear, and legislators responded with more severe punishments for criminals.

In her 2010 book, “The New Jim Crow: Mass Incarceration in the Age of Colorblindness,” civil rights lawyer Michelle Alexander argues that today’s criminal justice system is responsible for redesigning a racial caste system in America. The book has been described – even by some of its critics – as having successfully launched the effects of mass incarceration into the national consciousness.

“An extraordinary percentage of black men in the United States are legally barred from voting today, just as they have been throughout most of American history,” Alexander writes in the book’s introduction, referring to men with felony convictions.

“They are also subject to legalized discrimination in employment, housing, education, public benefits, and jury service, just as their parents, grandparents, and great-grandparents once were.”

But some say that the storyline isn’t as neat as Alexander suggests.

James Forman Jr., a professor at Yale Law School and son of civil rights leader James Forman, wrote in a 2012 article for The New York University Law Review that the Jim Crow narrative fails to fully recognize the dramatic increase in violence that the U.S. saw prior to the war on drugs.

“The analogy generates an incomplete account of mass incarceration — one in which most prisoners are drug offenders, violent crime and its victims merit only passing mention, and white prisoners are largely invisible,” Forman wrote. He argues that from 1959 to 1971 street crime quadrupled, and that between 1963 and 1974, homicide rates doubled and robbery rates tripled.

Nor, Forman wrote, does the analogy recognize the support that “tough on crime” policies had in black communities.

In Washington in the early 1970s, for example, members of the Congressional Black Caucus met with President Richard Nixon, encouraging him to step up the drug war.

Wintersmith’s attorney, MiAngel Cody, a federal public defender based in Chicago, said that although those laws weren’t implemented malevolently, they were a rash reaction to the inner-city drug problem.

“Yes, it was very bipartisan,” Cody said. “But the key fact is that it was kneejerk and it lacked the empirical evidence to support the mandatory minimums and the disparity between crack and powder.”

This disparity largely accounts for Wintersmith’s long sentence. Today, instead of 100-1, the crack-cocaine sentencing ratio is 18-1. But this policy change wasn’t retroactive, meaning people in prison for nonviolent drug crimes are serving sentences that simply wouldn’t be handed out now.

However, that may not be true for long.

“People are realizing that the legislative solution not only failed but it has perpetuated the problem,” Cody said. “People who are perpetrators of the drug epidemic, in my experience, typically are harmed by it first.”

Polls show the public is ready for a shift in focus. An April report from the Pew Research Center, a nonpartisan think tank based in Washington, D.C., found that 67 percent of Americans favor treatment for drug offenders over prosecution.

Kid to convict

As a child, Reynolds Wintersmith split his time between Rockford and Chicago. But no matter where he lived, drugs pervaded his life.

When he was 11, he lay next to his mother as she died of a heroin overdose, he says. After her death, he moved in with his grandmother. She didn’t use drugs. She sold them out of the house. When Wintersmith was 16, his grandmother was sent to prison. Someone had to take care of the home and the younger children living there. Wintersmith knew one way to do it: sell drugs.

Drug dealing allowed him to provide the things his family needed. For a while, he was able to send his little sister to the grocery store with $400 and tell her to fill up the cart.

His career as a drug dealer didn’t last long, about a year, Wintersmith said. But that was long enough for him to be considered a leader within the drug ring he worked.

He was arrested three weeks before his 20th birthday, and convicted as part of a conspiracy on four counts of possession of crack cocaine with intent to distribute, which added up to the sentence of life plus 40 years in federal prison.

Even the judge who sentenced him, following the mandatory minimum requirements, seemed taken aback by the sentence. “It gives me pause,” said U.S. District Judge Philip Reinhard, “to think that that was the intent of Congress, to put somebody away for the rest of their life.”

Time inside

Despite his life sentence, Wintersmith never believed that he would die in prison.

He remembers another inmate telling him, “You can do prison two ways. You can come here and die mentally or physically – you can make it your graveyard. Or, you can use it as a school and you can learn things that you could never learn anywhere else that will help you better your life.” It was advice he took to heart.

He started reading voraciously, books like the autobiography of Assata Shakur, who wrote about her life as a Black Panther, struggles against the government and subsequent time in prison. “Only way to empower yourself in a concrete box is if you grow mentally,” he said. Books gave him the confidence that he could get through whatever he was going to face, he says. His reading and conversations with other inmates allowed him to articulate the maze of emotions he felt about being locked up.

Lucas Payne, who works as a nightclub and talent promoter in Chicago, met Wintersmith while they were both serving time at a federal prison in downstate Illinois. He said it was apparent immediately that with Wintersmith’s character, focus and confidence, he would one day be released. The two men taught other inmates at a school in the prison.

“He still has served a role as a father, a big brother, a mentor. He’s been able to facilitate a lot of that from behind bars,” Payne said recently, reflecting on Wintersmith’s commutation.

To gain qualifications to teach, Wintersmith completed a 4,100-hour teaching apprenticeship program as an inmate. He also served as a counselor for inmates struggling emotionally to deal with their prison time.

And, Payne said, Wintersmith helped develop a curriculum used to teach lessons like the proper way to shake hands, be interviewed, make eye contact and speak in front of groups – a job-hunting course taught by a man sentenced to die in prison.

Wintersmith would tell Payne, “You struggle, I struggle – I struggle alone.”

“You don’t struggle alone,” Payne would respond. “Because your struggle is mine and it impacts all of us.”

Shift in the Obama Administration

Obama has been slow to implement reforms within the criminal justice system. For example, Wintersmith was one of 10 commutations the president has granted out of 14,406 requests. Though clemency petitions are historically rare, so far Obama has granted fewer than any president since Dwight Eisenhower.

That could soon change.

In January, a deputy to Attorney General Eric Holder asked both public and private sector attorneys across the country for help identifying federal prisoners who had been given far longer sentences than they would have received if convicted today.

Holder announced the White House wanted to consider more clemency applications “to restore a degree of justice, fairness and proportionality for deserving individuals.” This became known as the clemency initiative. In early May, surveys were sent to all federal prisoners, giving those interested a chance to explain why they would make good candidates for commutation.

Inmates submitted roughly 20,000 petitions in response, according to Molly Gill, director of government affairs for Families Against Mandatory Minimums, a nonprofit created to oppose mandatory sentencing laws. Attorneys, working pro bono, are looking for the strongest cases, and eligible candidates will be matched with the attorneys moving forward, Gill said.

In general, ideal candidates for commutation have served at least 10 years of their sentence, have not committed any violent crimes and were sentenced under laws no longer on the books, according to Deputy Attorney General James Cole.

Further, the Office of the Pardon Attorney, a part of the Justice Department that recommends clemency applications to the president, recently announced a change in leadership. Ronald Rodgers, who was heavily scrutinized after a 2008 Justice Department inspector general report found that he withheld important material from President George W. Bush regarding a clemency recommendation, has been replaced with Deborah Leff, a top Justice Department attorney.

Before Leff joined the Justice Department in 2010, she held various positions in the private, public and nonprofit sectors, including a stint as president of the Public Welfare Foundation, which focuses on criminal and juvenile justice reform. Her supporters say she has dedicated her career to fairer sentencing and support for low-income Americans, and that her appointment signifies the Obama administration’s willingness to revamp the clemency process.

Like the Smarter Sentencing Act, though, the clemency initiative recently hit roadblocks. In late May, the House voted to bar the Justice Department from hiring additional attorneys to help wade through backlogged clemency applications.

Rep. George Holding, R-N.C., who sponsored the amendment, said the clemency initiative is not “as the Founders intended,” but rather the “use of the pardon power to benefit an entire class of offenders who were duly convicted.”

“My amendment prevents the administration from abusing their power by not allowing for the expansion of the Pardon Office,” he said in an emailed statement in June.

‘I wish I knew how it would feel to be free’

What made Wintersmith’s clemency petition stand out in a sea of more than 14,000?

His lawyer identifies two factors:

The first is the facts of his case – teenager, no priors, assigned a life sentence; the second, Cody said, is simply that “the person he has grown into and become over the last 20 years has made the sentence even more unjust.”

The day Wintersmith heard news of his commutation started out like a lot of others.

He had just finished working out. He took some cool-down laps in the recreation yard while listening to music on his MP3 player. Then he was called to the assistant warden’s office. Cody needed to talk to him on the phone. He waited for the call back.

Fifteen minutes later, he was on the line with an ecstatic Cody. Neither she nor the associate warden’s secretary could believe how calm Wintersmith seemed. But Wintersmith said he just always knew that this day would come.

“I knew that the wall is just a wall, they all fall down,” he said. “Didn’t know when mine was going to fall down but when it did I was going to be ready for it.”

“I prayed for this, I expected it, I believed it. To me I didn’t have a reaction of disbelief because I never stopped believing that I was going to go home,” Wintersmith said.

Wintersmith smiles each time he tells the story of the song playing on his MP3 player when his name sounded from the loudspeaker that day.

“Nina Simone – ‘I Wish I Knew How It Would Feel To Be Free.’”

Moving beyond the headlines

At 6 feet 4 inches tall, Wintersmith is built like a linebacker, which he isn’t, and dresses like he works for a fashion company, which he has. After his release, he went to work for Barbara Bates of Bates Designs in Chicago. He lives on the West Side, in North Lawndale.

Building an ordinary life, he said, is his focus now.

“What I want are opportunities to show that I’m more than just a headline,” he says.

That’s not necessarily easy to do. Four out of every 10 offenders return to prison within three years of their release, according to a Pew report from 2011. And not all neighbors welcome former drug offenders into their communities.

Bates, his employer, provided some of the security that has helped Wintersmith move forward. He met her when she visited the halfway house in Chicago where he was transferred after his clemency announcement. Bates has been a motivational speaker at the halfway house for years.

Bates said she felt Wintersmith’s spirit when she first met him. Later, he called looking for an opportunity, looking for employment, looking for a chance. She didn’t need help at the time, but she granted him an interview anyway. She had a friend sit in with her, she recalled, “because sometimes I can be a sap.”

“I knew that he was sincere. Just looking back on the whole situation, I thought he needed a second chance. If Obama can grant him one,” she said, “then I sure can.”

Some people get out of prison and they look worn down. Their time behind bars shows on their faces. Bates said that when she met Wintersmith, she didn’t see the time on him.

Wintersmith played myriad roles for Bates. On an afternoon last May, he sat poised behind a cluttered desk, papers, magazines and clothing bits strewn about, a laptop in front of him.

He was impeccably dressed – a pink shirt with thin stripes, pressed slacks and dress shoes. Observant of the store’s constant commotion but not thrown off beat, Wintersmith spoke at length about his life in a quiet voice and with an easy smile.

Bates was with Wintersmith the day he was released, and she accompanied him to the WVON studios where he spoke with “Talk of Chicago” host Perri Small. He talked at length about his time behind bars. And he took calls from listeners across the Chicago area, listeners whose views reflect the impact drugs have on Chicago communities, particularly black ones.

One caller spoke about the challenges of large-scale reform, alleging wholesale clemency is too much ammunition for those opposed to it, and that there’s not much of a constituency that favors shorter sentences. Another caller asked him how he thinks the community should welcome back men and women like him who once brought so much pain to their neighborhoods. Because of drug dealers, the caller said, he can’t let his daughter play basketball in the local park.

Wintersmith said he wants to use his experience to help others understand the effects of drug dealing as well as severe sentencing. The time he spent in Washington in May is one way he is slowly trying to do that.

For Wintersmith, though, the only way to keep true to himself is to keep his focus right in front of him, to work one step at a time.

Just this week, he took another step forward. Wintersmith began working as a counselor at Community Christian Alternative Academy, a private high school in North Lawndale.

“I won’t measure how far along I am based on somebody who’s been out here with 20 years worth of experience and an accumulation of things,” he said.

“When the lights go off and the people stop talking about how the president commuted my sentence, then what am I still responsible for?

The life of Reynolds Wintersmith.”

This story was produced as part of the Social Justice News Nexus, an initiative at Northwestern University’s Medill School of Journalism that brings together reporters, community watchdogs and journalism students to cover issues that impact Chicago. Applications are currently being accepted for SJNN fellowships. Learn more at The Social Justice News Nexus is supported by the Robert R. McCormick Foundation.