One Year After Obama-Ordered Release, Former Drug Prisoner Finds New Career

By McCarton Ackerman 01/16/15

Reynolds Wintersmith once faced life in prison, but a presidential pardon granted him a new beginning.

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Reynolds Wintersmith
Reynolds Wintersmith via YouTube

Reynolds Wintersmith was one of eight drug defendants whose sentences were commuted by President Barack Obama in 2013, but the former teen inmate has taken his unlikely opportunity to devote his life to helping at-risk teens turn their lives around.

Wintersmith was raised by a drug-dealing grandmother in Rockford, Ill., and eventually turned to drug dealing to support his siblings. In 1994, at the age of 19, he was sentenced to life in prison after being charged in a federal drug conspiracy. But after being released last January with the help of Obama, he now has a home in Chicago and a job as a counselor at CCA Academy, a charter high school for at-risk youth in the city.

"I have 21 years worth of things to talk to them about. That is what I worked on every day in prison…freeing my mind and doing my best to gain mental fortitude,” said Wintersmith. "When I walked out of prison, it wasn't like something clicked. I had been carrying this in spirit all along."

The job is an extenson of the work Wintersmith engaged in while behind bars. He earned over a dozen certificates after taking courses in a wide range of topics from computers to suicide prevention, and also mentored many of his fellow inmates.

It was that determination to better himself which that Chicago fashion designer Barbara Bates first noticed. She met him at the Salvation Army halfway house, where he lived in the first few months after his release, and ultimately gave him a recommendation to CCA.

"He has convictions that are really strong." said Bates. "Convictions that most of us (who) have freedom don't think about. He doesn't get excited about the stuff the rest of us get excited about…He would only care if someone had a good heart."

CCA founder and principal Myra Sampson immediately hired Wintersmith and had him lead “talking circles” for the students, as well as smaller private talks between students who are in conflict. She said he fits in perfectly with the school’s restorative justice program, which promotes dialogue over punishments when dealing with student conflicts and behavioral issues.

"We think the whole school has benefited," she said. "He is definitely a good person…because of the way he listens and the way he helps to restore. When you feel that nobody hears you, or nobody wants to hear you, sometimes you have to get a little deeper with students. And I really think he hears."

Last month, Obama once again commuted the sentences of eight federal drug defendants, including four who either had life sentences or were on death row. The bold move is part of a broader effort by the Obama administration to help correct the errors of harsh laws for nonviolent drug crimes.

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McCarton Ackerman is a freelance writer and editor living in Portland, Oregon. He has been a contributor for The Fix since October 2011, writing on a wide range of topics ranging from medical marijuana in Colorado to the world's sexiest drug smugglers. Follow him on Linkedin and Twitter.

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