Rob Burgess

When I say the name Rick Ross, who comes to mind? If you’re conjuring a newly trim, tattooed rapper from south Florida, then you don’t know the half of it. The true story is way more interesting.

Making its television debut, the first part of the documentary “Freeway: Crack In the System” will premiere at 10 p.m. Sunday and conclude at 10 p.m. March 8 on Al Jazeera America, according to a Feb. 2 press release.

I have been on to the story told in this film for quite a while. Back when I was a reporter for the Ukiah Daily Journal in Ukiah, California, I was shocked to discover the rapper who calls himself Rick Ross is actually named William Leonard Roberts, a former prison guard. As I wrote in my Aug. 3, 2008 column, “When keeping it real goes wrong,” this situation resembled the 1993 Chris Rock mockumentary “CB4”, in which the identity of a prisoner (Charlie Murphy) is stolen by aspiring rappers.

Late last month, I had the opportunity to interview the real Rick Ross, the former drug kingpin whose life story is profiled in the documentary. A major story line in the movie, which I was lucky enough to preview, involves his ultimately unsuccessful legal battle to reclaim his name. “I pretty much have just moved on with my life,” he told me. Ross now sells T-shirts emblazoned with the words: “The Real Rick Ross Is Not A Rapper.”

One of the most fascinating parts is Freeway Rick Ross was earning more than a million dollars a day from crack sales in the 1980s, all while being illiterate. “Reading wasn’t something that I felt I could use, so I never picked it up,” said Ross, who has since founded the Freeway Literacy Foundation and now speaks to students across the country. “But once I was in prison and I got my indictment papers and whatnot, I found out for the first time there was something on a piece of paper that I wanted to know what it was.”

In fact, I think Ross has one of the most compelling stories for why reading is important. As the film shows, through his own legal scholarship he was able to win release from behind bars after being improperly charged.

“I was really smarter than my lawyer, my prosecutor, the judge and all the cops on my case because I was able to find something in the law that either they overlooked on purpose or they didn’t understand what they were reading,” Ross said.

Ross said he recognized award-winning director Marc Levin as the perfect candidate to tell his story, as he had been covering these issues for years. The film does an excellent job of showing how Ross was being supplied with cocaine by Nicaraguans raising money for the CIA-backed Contras through drug sales.

“I was at the Iran Contra hearings as a young producer for Bill Moyers on his [1987 PBS] special ‘The Secret Government,’ which won him and I an Emmy,” Levin told me in December. “So, I was there when Oliver North testified.”

Levin was later introduced to Ross by the late Pulitzer Prize-winning San Jose Mercury News investigative reporter Gary Webb. (Webb’s book, “Dark Alliance,” which I’m reading now, and a book about him, “Kill The Messenger,” by Nick Schou, which I’ve just read, also form the basis for the Jeremy Renner-starring drama of the same name released last year.) Levin said they met in person in 2006 and bonded over their shared love of tennis. After Ross was released from prison, he called Levin right away.

“[Ross] said, ‘I told you I’d get out. I’m on the bus ride home and you’d better get out to LA. Let’s make that movie we’ve been talking about,’” Levin said.

And now? Ross is still applying his entrepreneurial skills. He is selling his own book he co-wrote with Cathy Scott, “Freeway Rick: The Untold Autobiography.” He says he’s even looking for fashion designers for a clothing line.

“No matter where you’re at today, it doesn’t mean you have to stay there,” Ross said. “You can always fight to make it better.”

I highly recommend this film, which explores profound themes in recent American history and leaves the viewer on a hopeful note. This is one of those cases where truth is stranger than fiction.

Rob Burgess, Tribune night editor, may be reached by calling 765-454-8577, via email at or on Twitter at

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