The Obama 8: Stories from the Prisoners whose Sentences Obama Commuted

TIME talks to five of the federal crack-cocaine offenders whose sentences were commuted by President Obama

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Courtesy of Steve Hernandez /

Jason Hernandez and his son Estevan during a prison visit in 1999.

Read about Obama’s Legacy Project in this week’s TIME magazine.

None of the eight federal prison inmates whose sentences were commuted on Dec. 19 ever got a chance to vote for President Barack Obama, but they all tried, and succeeded, at making sure Obama knew their names.

The voices of the commuted prisoners, all of whom have served at least 15 years in life sentences for crack-cocaine related crimes, help tell the story of the Obama administration’s plan to fix what it sees as broken aspects of the criminal justice system. As we detail in a piece in this week’s magazine, the legislative and executive actions that make up that plan are slowly beginning to have an impact. The latest move saw Attorney General Eric Holder calling on states to restore voting rights to the nearly six million people disenfranchised because of felony convictions. Yet despite the executive actions and proposed legislation, thousands face sentences that would have been shorter if they were convicted under updated drug laws.

For a story in this week’s magazine about the president’s criminal justice reform record, I ended up speaking to five of “Obama’s eight,” most of whom are in low-security camps and halfway houses across the country awaiting their first step toward release back into society. They were all first time, non-violent drug offenders who got caught up in the tough-on-crime federal sentencing rules that attached long sentences to crack-cocaine involvement. Many of their stories were told in detail in an American Civil Liberties Union report on people sentenced to life for non-violent crimes.

These five people—Jason Hernandez, Helen Gray Alexander, Billy Ray Wheelock, Clarence Aaron, and Reynolds Wintersmith—have spent much of their lives behind bars, and expected to remain behind the wire until death, until their sentences were commuted.

Clarence Aaron was a 23-year-old college student when he was sentenced to life without the possibility of parole in 1993 for conspiracy to possess cocaine and crack after he acted as a middleman in a drug transaction. He maintained a job throughout his stint behind bars, continued his education (he collected certifications), and was able to save $1,000 a year.  “I could have died behind the fence, but I would have been happy with the things that I accomplished,” he said.

Now Aaron won’t have to die in prison, a fact he does not take lightly. “I went from having a death sentence to actually having a date where I can walk out of those gates and become a productive citizen again,” he said. “When I walked out of that fence, it was only the beginning.”

Reynolds Wintersmith, who was one of the youngest of the eight, got involved in a large-scale conspiracy as a teen and was convicted of distributing and possessing crack. He said when he found out his sentence was commuted he “knew he had work to do.”

“I’m not making a bucket list like I’m getting ready to die,” Wintersmith said. “God gave me the strength to endure and I hope to be able to share that with other people—that you can endure if you choose to. You can do extraordinary things even under bad conditions.”

Besides the extreme gratitude the five expressed (Hernandez said he was “indebted” to the President; Wheelock sent Obama a thank you note) the most compelling part of the experience for the prisoners was seeing the effect these commutations had on those still behind bars. According to Aaron, there was a sense of hope restored among those in prison facing lengthy sentences for non-violent crimes—hope that someone on the other side might just have their backs.

Helen Gray was convicted of conspiracy to distribute cocaine and possession of a firearm by a convicted felon in 1996. She said that leaving some of the women she encountered in prison made her sad. “You can’t help yourself in prison,” she said. One of her goals upon her scheduled release on April 17 is to start sharing her story with women and girls with hope that it will keep someone from facing a fate similar to hers.

Billy Ray Wheelock, who will be released from a minimum-security camp on Feb. 18, said that outside of prison he hopes to be the voice of those who have either died or remain behind bars. “My freedom comes with responsibility and commitment,” he said in a phone interview. Wheelock was sentenced to life in prison in 1993 for distributing more than 50 grams of crack and intent to distribute more than 5 grams within 1000 feet of a school.

Some of their goals outside of prison are more lighthearted. Wheelock plans to marry his fiancé, who he met online behind bars, two days after his release from a Denver halfway house. Jason Hernandez said he can’t wait to take care of his parents. And Clarence Aaron is really looking forward to taking a bath.

“I have had to take showers for 20 years,” said Aaron. “I just want to sit in a bath.”

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