Freeway Rick Ross: No Regrets, Only Lessons

Unlike the limitless stories of gangsters such as Al Capone, John Dillinger or even Sam Giancana—in the African American community, some of our most notorious former gangsters still live among us. While Ricky Donnell known as “Freeway Rick Ross” was serving a life sentence, rapper William Leonard Roberts adopted more than his name for the stage, but he elevated an image based on Ross’ bad boy lifestyle of being one of the country’s biggest drug traffickers in the 1980’s on the West Coast.
Ross was granted an appeal by the federal court of appeals because the Clinton-era three-strikes law was unconstitutionally applied to his case. With a reduced sentence, Ross served 20 years in prison and was released September 29, 2009.
The long stint inside of the prison system empowered his time inside to reflect and learn how to read at 28. There he studied intensely on the law, and therefore would discover a legal loophole that would lead to his release.
At 57, he has not taken his new chapter on life for granted. For the past couple of years, he has traveled around the country to promote and discuss his book Freeway Rick Ross: The Untold Autobiography co-authored with Cathy Scott. The book is an in-depth look into his life from his family’s native roots of South Texas to the intricate web of international drug trafficking.
My mom moved to Los Angeles when I was three years old hoping to introduce us to a new lifestyle. More opportunities. I think. In Texas, you probably just going to be a farm boy you know. Hauling hay, cutting wood, raising cattle. So, I think my mom decided that we would have a better opportunity in the big city,” he said.
Growing up in South Central, he fell in love with the game of tennis and excelled at it—often playing with pro players during their time off. Although he was attending high school—he could not read. His focus on his athleticism and not his academics derailed his chance of receiving a college scholarship. He began to work odd jobs and reverted to the street hustle—eventually selling cocaine for a former high school teacher.
Ross recalls his early days selling drugs. “I would sell to people who worked at the shipyard, postal workers, doctors, lawyers and pimps. People who sold drugs, who sold other drugs. Basically, it was the affluent people who really called the shots in the community. Most people don’t really understand that but the drug dealers had a lot of influence in our community—tremendous influence,” he says.
“That’s what I’m talking about in my book because I know once they read it, the rest of the country is going to want to know why this particular group is reading this book.”
He said it’s this group who is supporting his book.
“Well a lot of them are wondering well what can they do. You know I’ve met kids who went to college, got only degrees and can’t get a job. You know. It’s amazing how the society has a double standard.”
“We have to go above and beyond. You know when I was in prison, I started to write my book. I was thinking about what was I going to do when I got out. What kind of job can I get? Can I be gainfully employed? How can I take care of myself? I thought about when I got in the drug business.
“I thought about the tactics and the skills that I used to go from having $125, then tap into a business that was making hundreds of thousands and millions of dollars a month. I wanted to tap into that stream of income. What I did was not to focus on the money aspect,” he explains.

“I focused on learning as much as I could about the trade and becoming the best that I could. It wasn’t money with me, it was like a game. It was like playing tennis on the tennis court where I’m playing against Lawrence King who at one time was the second best Black tennis player in the world behind Arthur Ashe.”

Ross said King would work out with him and whenever he would hit the court, he would get an adrenaline rush because it was his “dream to be him.”
“That’s the way I went into the drug business where I was putting all of my energy, all my effort and all my thoughts into that.”
It’s been nearly 30 years and not much has changed with our youth, the country’s most rural and low-income communities. With the lack of jobs and education, the odds of earning a decent living influences youth to choose the illegal lifestyle of selling drugs and resorting to other forms of crime. Often critics look at lack of parenting and no parental presence at all, but Ross says his mother did the best she could under the circumstances in raising him.

Rap artist Rick Ross [William Leonard Roberts III]
“I mean it’s a double-edge sword. We have to look at our people. My mom’s father was a sharecropper and my mom used to pick cotton on the plantation. So, she was only allowed to go to school at certain times of the year. She never had the economical background that she needed to raise a serial entrepreneur,” Ross said. “I’ve been an entrepreneur all my life. I’ve collected cans and bottles. I’ve had car washes at 11 years old, I would round up my guys and my mom would always say, ‘You’re the ringleader,’” he remembers.
In 2010, Ross filed a copyright infringement lawsuit against William Leonard Roberts III for using the name Rick Ross under his stage name. He sought $10 million in compensation for the use of his name. The lawsuit was dismissed that same year and Def Jam moved forward to release Teflon Don in late July 2010. Ross refiled in the Los Angeles Superior Court and later updated a motion in his favor against Warner Bros. Records for the use of his name and image in July 2012. With a trial set in late August 2013 to seek compensation for use, the court ruled in favor of the artist Rick Ross based on First amendment rights. By this time, the damage was done and the rapper’s street creditability was in question.

“I mean for me it was just business– nothing personal. I don’t have anything against the guy personally. I may crack a joke every now and then because I’m going to radio stations, and the host may say something, but I don’t have any ill feelings toward this guy. If he walked in today, I would shake his hand and have a conversation with him,” he says. “My lawyer came to me and said Universal Music owes me $50-$100 million and he asked me if I wanted him go get it. I said, ‘absolutely let’s get it’.”

Ross says throughout his ordeal and lessons learned, he didn’t know if he would get out of prison. He wanted his book to be an open letter to other Black men and women who lost their way but could still find hope in the darkest places.
When asked if he had any regrets, he answered: “That’s a hard word, to regret something because that would mean that you made a mistake that you didn’t learn from. I don’t think I have any regrets. My 20 years I did in prison—if I could get it back, I wouldn’t because I enjoyed those 20 years in prison when I was there.” In reflecting back to those days he spent incarcerated, Ross started a book club to engage the younger inmates to read books.
I was telling them, these last four or five months inside—I’m enjoying because I’ll never get to do this again.”
This article is featured in the November 1 issue of The Chicago Defender. Mr. Ross will be making an appearance at a special anti-bullying celebrity charity event on Sunday, November 5 at the House of Hope located at 752 E. 114 St. from 5pm-9pm. 
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