The Wild Story Of ‘Freeway’ Rick Ross, The Crack Kingpin Who Literally Read His Way To Freedom

Published May 4, 2023
Updated May 5, 2023

After building a $900 million drug empire in 1980s Los Angeles, "Freeway" Rick Ross was sentenced to life in prison — but then he got out and reinvented himself.

In some ways, “Freeway” Rick Ross was a rags-to-riches, American business success story. An illiterate high school dropout, Ross shattered the public’s expectations by becoming a self-made multimillionaire. Unfortunately, he made his fortune by selling crack cocaine.

Ross didn’t invent the drug or smuggle it into the United States, but he did help popularize it. For much of the 1980s, he successfully marketed his commodity as an outlaw businessman in Los Angeles and beyond. But as Ross built his empire, impoverished people in communities around him suffered from addiction, violence, and widespread turmoil.

Shockingly, it was later revealed that Ross may have been a small pawn in a much larger game. In 1996, investigative journalist Gary Webb linked the CIA to the crack epidemic, claiming that the agency had funded a guerilla army in Nicaragua that used crack cocaine sales in Los Angeles to finance an attempted coup of Nicaragua’s socialist government. And unbeknownst to Ross, one of his drug trafficking mentors was working for the guerilla army.

After narrowly escaping a life sentence in prison, Ross didn’t get the chance to retire with his illicit fortune. But his story didn’t end there. A resourceful dreamer, Ross decided to make a new fortune — the legal way.

How “Freeway” Rick Ross Became A Multimillionaire Drug Kingpin

Freeway Rick Ross

@_ValTown_/TwitterA rare photo of a young “Freeway” Rick Ross.

Ricky Donnell Ross was born on January 26, 1960, in Troup, Texas. His family relocated to Los Angeles when he was three and settled in the South Central area. They lived near the 110 Freeway, which helped inspire Ross’ nickname.

Growing up in poverty, Ross showed interest in making money from a young age. He mowed his neighbors’ lawns, sold lemonade, and pumped gas. But there were also early signs of trouble, as he also shoplifted, ran errands for pimps in his neighborhood, and fought his classmates at school.

Eventually, however, the young Ross discovered a talent for tennis. In high school, he was good enough to attract the attention of a recruiter at Cal State Long Beach. But according to Vice, Ross’ hope for a tennis scholarship faded away when coaches learned that Ross still didn’t know how to read.

Though Ross had apparently come close to failing his classes many times because of his illiteracy, he later said that his high school coach ensured that he stayed enrolled in school. But Ross would ultimately drop out before graduation, and another type of education would soon begin.

Crack Cocaine

DEA/Wikimedia CommonsA DEA photograph identifying the street dosage of crack cocaine. Crack — which was made by cooking powder cocaine with baking soda and water — was popular in the 1980s due to its cheap price and high purity.

At some point in the late 1970s or early 1980s, Ross bought cocaine for the first time for $50. But the day after buying it, he decided to sell it — for $100. While some people in his neighborhood were just starting to get hooked on the drug, he got hooked on making money from it. According to the Detroit Metro Times, Ross did try using cocaine at one point, but failed to get high from it, which likely helped him from a business standpoint.

Essentially, “Freeway” Rick Ross fell into the crack trade almost overnight — and knew that he was onto something huge. This was especially true when he met a Nicaraguan-born drug trafficker named Oscar Danilo Blandón. With Blandón came seemingly unlimited amounts of cocaine, and thus, seemingly unlimited cash for Ross when he started dealing with him.

According to Ross, he was a millionaire by the age of 23, largely thanks to help from Blandón, who was not only his supplier but also his mentor. But his newfound wealth was also undoubtedly helped by the 1980s crack epidemic, which wreaked havoc on Los Angeles and beyond.

It was only a matter of time before Ross’ business would expand to dozens of other cities in the United States, making him even wealthier. Ross invested most of his money in real estate across Southern California, but he didn’t keep it all to himself. He helped his mother refurbish her church, sponsored a semi-pro basketball team, and established a youth tennis program in the impoverished neighborhood where he grew up.

And to keep himself under the radar, he was careful to dress modestly and drove around in a beat-up car so he wouldn’t attract too much attention from the authorities. But he couldn’t avoid the spotlight for long.

A Long Legal Battle For “Freeway” Rick Ross

Freeway Rick Ross In Prison

Patrick Tehan/MediaNews Group/The Mercury News via Getty Images“Freeway” Rick Ross in 1996, shortly after he’d received a life sentence.

“Freeway” Rick Ross was first investigated by the Los Angeles Sheriff’s Department in 1985, but they struggled to pin anything on him. So, two years later, the Los Angeles Sheriff’s Department teamed up with the Los Angeles Police Department to form the “Freeway Ricky Task Force,” according to the U.S. Department of Justice Office of the Inspector General.

In April 1987, some members of this task force attempted to set Ross up. Ross had apparently escaped a police foot chase one evening, so officers decided to plant a kilo of cocaine along the route that he had taken, but the charges were later dismissed due to police misconduct.

Later in the 1980s, however, cocaine bound for Ross’ territory in Cincinnati was linked to him. This time, he couldn’t avoid arrest — and he was indicted in cases not only in Cincinnati but also in Los Angeles and Tyler, Texas. Prosecutors later estimated that, between 1982 and 1989, Ross had resold three tons of cocaine, with gross earnings of $900 million. He pleaded guilty to drug-trafficking charges and was sentenced to 10 years in prison.

He began serving his prison sentence in 1990, but it was unexpectedly cut short — due to the massive corruption in the sheriff’s office that had pursued him so relentlessly. According to Esquire, a federal investigation revealed that authorities at the sheriff’s office had not only planted evidence but had also stolen drug money and brutally attacked suspects.

Ross was offered an opportunity to testify for the government in exchange for serving less time in prison, and he agreed. Because of this, he was freed less than five years into his original sentence. It was then that Ross began to attract media attention, and it seemed like many people were eager to see him turn his life around. Even a probation officer admitted, “He was more like a Robin Hood-type guy. You never heard of him getting high or drinking or beating women or dealing dope to kids. The guy really had a reputation for helping people out and giving money back to the community.”

However, “Freeway” Rick Ross wouldn’t be free for long. He’d soon be ensnared by his former supplier Blandón, who, unbeknownst to Ross, had become a paid federal informant after narrowly avoiding a life sentence. Blandón claimed to Ross that “the Colombians” were on his back and that he desperately needed money, so Ross agreed to help him out.

Gary Webb

Scott J. Ferrell/Congressional Quarterly/Getty ImagesGary Webb was an investigative journalist who informed “Freeway” Rick Ross about who his mentor really was.

Then, on March 2, 1995, in a parking lot near San Diego, Ross was busted during the deal by the DEA. He was later found guilty of conspiring to sell drugs that had been provided by the DEA. This was considered his third felony conviction, so this time around, he was sentenced to life in prison.

Not long after he began his life sentence, Ross received a visitor: investigative journalist Gary Webb. It was only then that Ross learned about Blandón’s link to the Contras, a group of rebels who had been trying to overthrow the socialist government of Nicaragua in the 1980s. As Webb told it, Blandón had been selling drugs to finance the Contras’ weapons.

Webb, who would later publish the exposé “Dark Alliance,” alleged that the CIA was purposely funding the Contras, knowing full well that these rebels were using crack cocaine sales in Los Angeles to fund their attempted coup. Ross, who knew little about Blandón’s past, was shocked to hear that he may have been a pawn all along. (This allegation may have also explained why Ross was able to get away with selling drugs as long as he did.)

While all hope seemed to be lost for Ross, he made good use of his time in a prison library — and taught himself to read at age 28. While reading, he discovered a technicality in his case that would allow him to spend less time in prison.

He learned that his prior convictions in Texas and Ohio had originated from the same federal crime, so they should have counted for “one strike,” rather than two. That would mean that he was on his “second” strike rather than his third and that his sentence would have to be reduced.

His lawyer was skeptical, but it turned out that Ross was correct. His sentence was soon reduced to 20 years, and he ultimately ended up serving just 14. Ross was officially released in 2009, and he still walks free today.

The Reformation Of A Former Drug Kingpin

Freeway Rick Ross In New York

Ray Tamarra/GC Images“Freeway” Rick Ross promotes his autobiography in New York City in 2015.

Since his release in 2009, “Freeway” Rick Ross has reinvented himself as an author, actor, prison reform activist, and legal cannabis entrepreneur.

He’s also sued the Miami rapper Rick Ross — whose real name is William Leonard Roberts II — for taking his name and appropriating his identity. The legal battle, which lasted about three years, ultimately ended with the judge ruling in favor of the rapper on First Amendment grounds.

Still, “Freeway” Rick Ross found success publishing his book Freeway Rick Ross: The Untold Autobiography and working on documentaries like Freeway: Crack in the System. He’s also diversified his role as an entrepreneur by distributing a variety of products, including legal cannabis.

Though Ross may have once felt that selling crack cocaine was his only path to success — and it may have been difficult to start over again without the money that he made as a kingpin — all the books he read while in prison clearly gave him the multimillionaire mindset once again.

And despite Ross’ checkered past, he’s also been tapped as a motivational speaker, often surprising those who heard what he had to say.

In an interview with BET, he said, “I was in Detroit… speaking at a school, and when I came in, the principal was scolding me, like, ‘This is how you’re gonna talk to the kids!’ and, ‘You ain’t gonna do this and that!’ But once he heard me speak he followed me out of the school and was like, ‘Man you can come here and do whatever you wanna do man! I appreciate you, man.'”

He added, “So, there’s still a misconception, even among Blacks, on how they view somebody with a drug dealing past. I think it’s ingrained in their mind that you’re this mindless sociopath that just made money exploiting the community and I just want to show America that even good people will do bad things when there are no options.”


After learning about “Freeway” Rick Ross, read about “White Boy Rick,” the FBI’s youngest informant who uncovered the largest corruption case in Detroit history. Then, see some images of real life in 1980s Los Angeles.

author
Neil Patmore
author
A true crime specialist, Neil Patmore served as a police officer in the UK for nine years, and a private investigator for three years before becoming a writer.
editor
Jaclyn Anglis
editor
Jaclyn is the senior managing editor at All That's Interesting. She holds a Master's degree in journalism from the City University of New York and a Bachelor's degree in English writing and history (double major) from DePauw University. She is interested in American history, true crime, modern history, pop culture, and science.