Conversations with an O.G.: Freeway Rick Ross

Collage art featuring Rick Ross
(Digital art by Greg Dubois)

by Calvin Stovall

“I can’t believe it. They allow me to sell dope legally. But I’ma do the right thing with this. I ain’t gonna do like some of these clowns who forget about their people.”

– Freeway Rick Ross

“Freeway” Ricky Ross is more than just an O.G. in the cannabis industry. Long before weed was legal in California, cannabis activist and entrepreneur Freeway Rick Ross was one of the most profitable drug lords in American history. 

By 1982, before the age of 23, Rick was a college dropout making $3 million a day selling cocaine to local gangs via a Nicaraguan connection. To hide the astronomical revenues from his mother, he invested in real estate and creative projects like Anita Baker’s 1983 debut album, The Songstress

Federal prosecutors estimate that from 1982 to 1989, Rick moved metric tons across 42 cities, stretching between New Orleans and Seattle. He grossed $900 million and took home a $300 million profit in 1980s dollars ($2.5 billion and $850 million today, respectively), but was eventually sentenced to life in prison.

While incarcerated, Rick taught himself to read and found a legal loophole that led to an early release in 2009. Since then, he’s embraced cannabis culture, and remade himself as a legal entrepreneur and political activist who organizes nationally against mass incarceration and systemic racism.

During his time as a cocaine dealer, Rick had no idea he was potentially being used as a pawn in the CIA’s Iran-Contra scandal, which reportedly smuggled cocaine into the US from Nicaragua to fund a revolution against their socialist government. A 1996 profile tying Rick and his Nicaraguan partners to the US government operation won writer Gary Webb the journalist of the year award and inspired the 2014 film Kill The Messenger, shocking the public andraising new questions about the causes of the 1980s crack epidemic. 

What BET’s SMOKE: Marijuana + Black America showed us about the future of weed

Though many details of the cocaine conspiracy are still clouded by government interference and outside speculation, Webb’s reporting cemented Rick’s name as legendary to aspiring kingpins worldwide. Ross recently appeared in Netflix’s new documentary, Crack: Cocaine, Corruption, and Conspiracy, which claims “the war on drugs funded policing.”

Multiple rappers and film projects have since appropriated Rick’s likeness to boost their own street cred, and his life story has become the source material for documentaries, films, and award-winning series. But few have taken the time to highlight his present-day activism and legal hustles. 

From his LA Kingpins cannabis brand, to restorative justice work that has already changed countless lives, Ross is as driven as ever. And his victim to victor triumph over the war on drugs is far from the end of his journey. Rick’s new hustle is creating legal opportunities for Black entrepreneurs in cannabis.

When did you start selling cannabis legally?

“I got into cannabis about seven years ago. I almost started the day after I got off parole. I wasn’t planning on getting into it. It wasn’t something that I was planning to be in. But one of my friends took me to one of the Cannabis Cups and when I saw the way it was going, I just fell in love with it. I knew it was the lane I wanted to be in.”

“Absolutely. It’s changed my life. I was struggling when I started selling marijuana. It allowed me to get enough money to where I could get a place. Now, I’m gonna share my success with everybody else.”

Were you a smoker when you were younger?

“Nope. I wasn’t a smoker then. I don’t smoke now. What I do is I eat it, though. I ate my first edible the day I went out to the Cannabis Cup event. So far it’s been smooth sailing.”

What do you do with the National Diversity & Cannabis Inclusion Alliance?

“I joined that board about four years ago. What NDICA does is makes sure Black and Hispanic people are included inside the cannabis industry. It’s an industry that’s controlled predominantly by White males, and we felt that most of the people who went to prison for selling marijuana were Black.”

What are the perks of your new career versus your old one?

“Cocaine is very highly addictive, and it hurt a lot of people. But marijuana helps people. Even myself; I usually do my edibles at night before I go to bed, and it gives me a good night’s sleep. Normally, I’m waking up throughout the night. 

A lot of people don’t know, but when you do 20 years in prison, it’s kind of stressful, and you have these nightmares like you’re back in prison. Marijuana helps me get around those.”

When the first round of licenses was granted, felons were excluded from participation—how did you secure a license? 

“We organized a group of people. It wasn’t but like 75 of us. We went downtown to city hall, from congressperson to congressperson, and said look: Not only do we want Black people to get licenses, but we want Black people with felonies to get a license. Why not? Everybody in this industry is doing something that was at some time illegal. That’s how you have to accomplish it.”

“Once they federally legalize it, a lot of money will come off the streets. People won’t be at their houses with hundreds and thousands and millions of dollars in cash, which creates crime. I think it will be more legitimate, allowing people to put their money in the banks and allowing credit cards to be used for purchases.”

Do you like to see your legend retold on the screen in stuff like Snowfall, Kill The Messenger and the lyrics of multi-platinum rappers?

“It’s bittersweet. On one hand, you’re glad that they recognize what you do. But on the other hand, it’s disappointing because they don’t give you anything out of it.”

How accurate are the stories about you in Snowfall and Kill The Messenger?

“Well, I participated in neither one. So right off the bat, that makes me leery of anything that somebody would be doing, and you have the actual person that lived the life and you don’t consult with him. To me that’s alarming.”

Besides the documentary Freeway: Crack in the System, what version of your story do you co-sign as authentic?

“My partner did one, 100 Kilos, that’s pretty accurate. I liked the documentary BET did with Reginald Hudlin. But for people who want to know more about me, they can go read the LA Magazine article they did on me in 2013, as well as the Esquire article they did in their 80th anniversary issue. Both of those are some really good articles.”