Meet Three Ex-Drug War Prisoners Doing Amazing Things With Their Lives

Don Diva Kev n Diddy II
Apr 21 2016

Meet Three Ex-Drug War Prisoners Doing Amazing Things With Their Lives

April 22nd, 2016

Reentering society after serving time in our nation’s correctional facilities thanks to the misguided War on Drugs can be a strangely disheartening experience. Sure, it’s a chance for a new start in life—something we’ve waited for for months, years, or even decades. But for many of us, the stigma of a felony hanging over our head makes it hard to get a job, to get credit or even to find a place to live.

With recidivism rates hovering nationally at 50 percent or higher, it’s an ever-present reality that many ex-drug war prisoners will end up back in prison. Unfortunately, because of the many barriers formerly incarcerated people face, success stories are just not that typical.

But they do exist. And I’m trying to be one myself. I earned a master’s degree during my 21 years of continuous incarceration for a first-time, nonviolent drug offense. I was released in 2014. And from my own experiences I know that the harder you work while inside, the better your chances of making the transition.

I spoke for The Influence to three other ex-drug war prisoners, who have each done their time and gone out in the world to put their talents to use, to find out how they made a successful reentry. They refused to let their felony convictions or the years stolen from them affect their future.

I hope you’ll find them as inspiring as I do—even if we cannot forget how many other human beings are left inside, and how much more needs to be done to heal the damage.

Inspired by Socrates

Michael Santos, now 52, spent 26 years inside the Belly of the Beast after being convicted of running a cocaine trafficking ring in Seattle. “I started selling cocaine when I was 20,” he tells me. “Those bad decisions led to me being arrested and convicted and sentenced to serve 45 years.” Remarkably, he didn’t give up. “Even though I was at the start of a term that would keep me in prison for decades, I knew that I wanted to change.”

On the street Santos’ mindset was straight Scarface, but after getting locked up he found a new muse.

“Soon after a jury convicted me, I found a story that described the life of Socrates. That story spoke to me because Socrates was in jail awaiting his execution. When I read his logic for declining an opportunity to escape punishment, I learned a great deal,” Santos relates. “After reading about Socrates, I realized that I’d been living by a bad philosophy.”

Despite the length of time he had to serve, Santos set himself goals that he hoped would allow him to reconcile with society and bring new focus to his life. He put a three-part strategy in place: He would work to educate himself, work to contribute to society, and work to build a support network.

He succeeded beyond his wildest ambitions.

“While incarcerated I earned a bachelor’s degree and a master’s degree,” Santos says. “Publishers brought several books of mine to market, and university professors used those books to teach students.”

Santon prisoners talk

Inspiring fellow prisoners.

Santos was released from prison in 2013. “Three weeks after concluding my obligation to the Bureau of Prisons, I began teaching as an adjunct professor at San Francisco State University,” he says. “Simultaneously, I worked to create programs that I hoped would help more people emerge from prison successfully.”

In essence, Santos hit the ground running, and instead of looking back with regret for his own lost years, he’s doing all he can to improve the prison system for others.

He’s found plenty of personal success, too. Today, he has a full-time job and owns five properties, with an ownership interest in three growing businesses.

Santos suit

“I’m very passionate about working to improve outcomes of our nation’s prison system,” Santos says. “In truth, the preparations I made in prison had everything to do with the success I experienced after the prison term concluded. I also metthe love of my life and we married inside of a prison visiting room. ”

Santos wife visit

Santos with his wife, Carole, during a prison visit.

Michael Santos is also the host of the Earning Freedom podcast, which interviews and profiles other people who have emerged successfully from the prison-industrial complex. Through his work as a prison consultant, professor of criminal justice and prison reform advocate, Santos is writing a whole new story for himself.

The Publisher

At 28 years old, Kevin Chiles was facing a natural life sentence under the federal kingpin statute as the head of a continuing criminal enterprise. Labeled by the government as one of the biggest drug dealers in Harlem since Nicky Barnes, he was arrested along with 21 associates and family members in the fall of 1994. After two trials and two hung juries, Kevin’s lawyer’s negotiated a 10-year prison term.

His environment shaped the young man he became. “Seeing my mother struggle forced me to forego my childhood and get out and hustle at the age of 12,” Chiles, who is now 48, tells me. “I wanted to do whatever I could to make a difference in my circumstance. Back then, I would buy what was called a fat dime bag and be able to roll a minimum of 20 joints to sell, doubling my money.”

In Harlem, the drug dealers were the stars of the neighborhood, reveling in their notoriety. To the young kids coming up, the cars, jewelry, money and women that the drug dealers had access to seem like the American Dream.

“I had an uncle who turned out to be my biggest influence and mentor of sorts. My uncle was a street hustler, selling cocaine and heroin.” says Chiles. “One day I got the courage to ask him to sell me some cocaine for a friend. I bought 7 grams, 1/4 of an ounce. Back then cocaine was really expensive, about $50,000 a kilo. That breaks down to what I purchased being about a $700 investment in 1982.”

His hustling career over, Chiles found himself in federal prison. But being a forward-thinking individual, he developed there the ideas that would launch Don Diva magazine, the original street bible covering hip hop’s lyrical lore, from his cell block.

“Five years into my sentence, with another three-and-a-half years to go before my earliest release date, opportunity knocked,” Chiles recalls. “A former girlfriend who worked in the music industry started visiting me frequently. She was running an upstart record company and would often discuss her marketing ideas with me.”

It was on a visit in 1999 that Chiles came up with the concept that birthed Don Diva. Soon, it grew into a well respected publication that sold all over the world and was huge in the hip-hop industry and urban community. Tiffany, the former girlfriend, became the editor-in-chief of the magazine, as well as Kevin Chiles’ wife. “She’s my business partner, my life partner and the mother of my youngest child,” he says.

jail visit photo

Kevin Chiles with his wife, Tiffany, on a prison visit in 2001.

Seventeen years later, their enterprise has evolved into Don Diva Global Media, a digital media company focused on bringing cutting-edge opportunities to other minority entrepreneurs. They’ve formed business relationships with some of entertainment’s most influential figures, like P. Diddy, 50 Cent, Floyd Mayweather and Cash Money Records (they’re pictured with Diddy and others above). And their website is today one of the top urban sites on the internet.

Making the News

Growing up, Keri Blakinger, now 31, was a competitive figure skater with Olympic aspirations. She skated pairs and competed at Nationals twice, but when her skating career ended, she hit some problems and started doing heroin. She kept doing heroin—and pretty much any other drug she could find—off-and-on for the next nine years. She became severely addicted.

“I got arrested in 2010 during what should have been my senior semester at Cornell.” Blakinger tells me. “I was sentenced to 2.5 years behind bars—which was incredibly lucky, because I would have gotten 15-to-life under the old Rockefeller laws—and served 21 months. Eventually, Cornell allowed me to finish up that last semester and I graduated in 2014.”

Graduation 1

Graduation day

But when she got out of prison in 2012, she wasn’t sure what she wanted to do with her life. She didn’t know how to get around her past in the career world, or even if she could ever be in the career world. The stigma of “addict” or “ex-con” stuck to her uncomfortably. It was hard to envision success.

“I attempted to avoid my past.” Blakinger says. “But I quickly found out that was often difficult to do. Part of it was the fact that my initial arrest received a fair amount of publicity. Part of it was the many restrictions associated with being a newly released felon. Part of it was that I felt, and probably looked, like a deer in headlights, baffled and unsure about how to readjust in society.”

A large chunk of her life had been consumed by addiction and then by incarceration. It permeated so many aspects of her life that it was often difficult to pretend it didn’t exist. So she stopped trying. She realized the only person she could be is who she was.

“I know that I don’t deserve to be judged by my past anymore and I will not hide who I am today out of fear of what people will think about what made me who I am today,” Blakinger says. “I’ve made it a part of who I am today. I have learned that people will judge me regardless—but when I embrace my past they are judging me on my own terms instead of theirs.”

Blakinger started communicating openly about her arrest and addiction in 2013 for an article on local heroin use in the Ithaca Journal. After more freelance writing, she parlayed her talents into her current job: at the New York Daily News. In an age that desperately needs progressive criminal justice reforms, her voice is one that should be listened to.

“I write for the New York Daily News, which means that I have an incredible opportunity to give voice to important issues,” says Blakinger. ”Obviously, what goes on inside the crazy and shady world of the prison system is something that interests me on a personal level. Before my arrest I really didn’t know jack about the criminal justice system. But once I got out I realized that a lot of other people didn’t really know jack either.”

And these days, she is busy informing them, combining her personal success with working for the greater good.

IC speech

Keri Blakinger giving a speech about her experiences.


Seth Ferranti was released in 2014 after serving 21 years for a first-time, nonviolent drug offense. He blogs at gorillaconvict.com and his latest book, Gorilla Convict, is a compilation of his writings about prison gangs, the mafia, hip-hop and hustling. His last piece for The Influence was “Is Drug Dealing a Hard Habit to Kick? Just Ask Former Kingpin ‘Freeway’ Rick Ross.” You can follow him on Twitter: @SethFerranti.