OK, so let's unpack this. We hear a lot of stories
about the American dream. Oh, absolutely. You
know, the whole idea that you start with nothing.
You pull yourself up by your bootstraps and you
build this massive empire. The classic narrative.
Exactly. But usually when we talk about that,
we are talking about, I don't know, tech startups
in a garage or real estate moguls in Manhattan.
Yeah, we definitely aren't usually talking about
a guy who at his absolute peak was pulling in
three million dollars a day. A day. Yes. Three
million a day selling drugs. And doing it all
while being functionally illiterate. That is
the part that always gets me. He couldn't even
read the street signs on the very freeway he
was named after. It's wild. So today we are doing
a deep dive into the life of Ricky Donald Ross.
And I want to stop you right there if you're
listening because I know exactly what you're
thinking. You're picturing the rapper. Right.
You're picturing the guy with the big beard,
the sunglasses, shouting Maybach music on the
radio. And that is a very, very common point
of confusion. But the man we are talking about
today is the actual inspiration for that name.
Yeah. We are diving into the source material
surrounding the real freeway Rick Ross, the man
who, according to estimates from our sources,
grossed over 900 million dollars in the 1980s,
which if we. If we run the inflation calculator
to adjust for 2025 numbers, that sits somewhere
around $2 .7 billion. It's staggering. Staggering
wealth. I mean, that is Forbes list territory,
but completely off the books. It is. But what
makes this deep dive so compelling, looking through
all these documents and reports, isn't just the
money. Right. It's the sheer contradictions of
his life. We have a man who was a central figure
in the US crack Copain epidemic, who became linked
to a massive CIA. scandal and yet his entire
criminal career essentially started because of
a massive failure in the public education system.
Yeah the education piece is huge and then his
exit from prison that only happened because he
taught himself to read after he was already locked
up for life. It really is a wild ride. So let's
go back to the beginning to figure out how this
happened. Before he was a kingpin Ricky Ross
was just a kid at Susan Miller Dorsey High School
in Los Angeles. Right. And here's the kicker.
He wasn't trying to be a criminal. He wasn't
out there looking for a hustle. He was actually
trying to be a tennis player. And by all accounts
in the sources, he was a phenom. He wasn't just
good for a high schooler. He was actively being
scouted. Wow. He had real hopes for a college
scholarship. Tennis was supposed to be his ticket
out of South Central L .A. But this is where
we hit that sliding doors moment. The barrier.
Precisely. He was illiterate. He had gone through
nearly 12 years of public schooling, and he still
couldn't read or write. That's just a colossal
failure by the schools. Totally. He was relying
on charm, a good memory, and his athletic ability
just to get by day to day. But when the colleges
actually found out about his reading level, the
scholarship offers were reneged immediately.
You just have to imagine that psychological blow.
You know, you have a path, you have a talent,
and the system fails to teach you the absolute
basics. Suddenly that door just slams shut in
your face. And he dropped out of high school
just weeks before graduation because he knew
he wasn't going to get the diploma anyway. So
now you have a young man with ambition, but no
degree, no reading skills, and no scholarship.
He's drifting. Right. And this is where you'd
expect the movie script to kick in. Like, He
meets a cartel boss in a dark alley or something.
A total Scarface moment. Exactly. Yeah. But it's
actually much more mundane, which I think makes
it way more interesting. He didn't meet a cartel
leader. He met an upholstery teacher. Wait, an
upholstery teacher, like fixing couches. Yes,
literally fixing furniture. Ross was hanging
around a local trade school or community college
just trying to figure out his next move. And
this upholstery teacher he befriended revealed
that he dealt cocaine on the side. Wow. Yeah.
And he offered Ross a small amount to sell. That
is just, you really can't make that up. The banality
of evil, right? So Ross takes this small amount,
he sells it, and then he uses the profit to buy
more, and just keeps flipping it. He's basically
applying basic business principles. Well, compounding
interest, essentially. Right, compounding interest,
but just to... a highly illegal product. And
he was incredibly good at it. He had a natural
mind for numbers, even if he couldn't read the
words on a page. He quickly outgrew the teacher
supply. So this is where he starts climbing the
ladder. Exactly. The teacher introduces him to
his own supplier, a man named Ivan Arguelles.
This connected Ross to larger quantities and
much better prices. He went from dealing grams
to dealing ounces. But the drug trade isn't exactly
a stable corporate environment. People get hurt.
No, it is not. About eight months into this,
Arguelles is shot in the spine. Man. He survives,
but he's hospitalized and effectively out of
the game. So the business shifts over to Arguelles'
brother -in -law, a guy named Henry Corrales.
Okay. But Corrales didn't really have the stomach
for the violence and the risk that comes with
the trade. And this right here. based on all
the sources, is the moment that changes everything.
Yeah. Because Corrales introduces Ross to a contact
who would catapult him from a local LA dealer
to a national figure. Enter Danilo Blandon. If
you study the history of narcotics in America,
Blandon is a massive, pivotal figure. Right.
He was in Nicaraguan exile. He wasn't a street
dealer. He was highly educated. He had a master's
degree in marketing. And he was part of a major
political movement. He saw the sheer volume that
Ross was moving and was highly impressed. So
when Corrales retired, Ross just started dealing
directly with Blandon. Exactly. And this relationship
is crucial because of the economics involved.
We need to geek out on the numbers for a second
here because this is where Freeway Rick Ross
really changes the game. It wasn't just about
selling drugs. It was about the price point.
This is a classic supply chain advantage. Through
Blandon and Blandon's own supplier, Noren Menises
-Cantarero, Ross was suddenly getting Nicaraguan
cocaine at significantly reduced rates. He cut
out all the local middlemen. We see this in legitimate
business all the time. If you can get your cost
of goods sold down, you can undercut the entire
competition. It's basically the Walmart model.
And he executed that aggressively. At the time,
cocaine was mostly a rich man's drug. A kilo
of powder cocaine could cost as much as $60 ,000.
It was highly exclusive. Yeah. But Ross was able
to drop that price down to as low as $10 ,000.
Wow. From 60 grand to 10 grand. That's an 83
% price cut. That effectively collapses the existing
market. And that massive price drop is exactly
what allowed the market to expand so violently.
It made the drug accessible to street gangs,
specifically the Bloods and the Crips, who previously
just couldn't afford that kind of volume. Right,
because now they could buy it cheap, cook it
into crack, and sell it for a few dollars a hit.
Exactly. He wasn't just selling to elite wealthy
users anymore. He was democratizing the supply,
for lack of a better word. And the volume was
just insane. The sources say he was purchasing
a thousand pounds as 454 kilos of cocaine every
single week. And selling up to three million
dollars in a single day. That's where the freeway
name comes from, right? It wasn't because he
was fast on the tennis court. It was because
he owned properties all along the Harbor Freeway
Interstate 110 in Los Angeles. That's right.
It was a massive logistics network. And despite
his illiteracy, the operation was incredibly
sophisticated. They were using tech, right? Oh,
yeah. They used police scanners, voice scramblers.
They were often technically ahead of the law
enforcement agencies that were trying to catch
them. There's actually a quote from a Los Angeles
county sheriff who admitted Ross's men had better
equipment than the police had. I love the detail
in the source material about how they handled
the money, though. They're making millions of
dollars. But Ross is absolutely terrified his
mother is going to find out. It's such a human
element in the middle of this massive criminal
enterprise. Yeah. In a jailhouse interview later
on, he admitted they were investing in houses
and legitimate businesses, partly just to hide
the cash from their mothers so they wouldn't
see them spending lavishly. Because you can't
exactly just leave a giant pile of cash in your
mom's living room. Right. And speaking of investments,
didn't he put money into Anita Baker's first
album? He did. A portion of his proceeds went
into funding that album. It really shows these
strange intersections between the underworld
and legitimate pop culture. The crack epidemic
proceeds were inadvertently funding smooth R
&B. Exactly. Okay, so we have the rise of the
empire. But we have to talk about the controversy.
Because you mentioned Danilo Bland and the Nicaraguan
exile. This leads us to one of the most explosive
political scandals of the 90s. The Dark Alliance.
Yes. This is where the story gets really heavy.
For you listening, we want to be clear that we
are just reporting what the sources outline here,
not taking any political sides. In 1996, a journalist
named Gary Webb wrote a series for the San Jose
Mercury News. Right. And he alleged that this
wasn't just a simple drug deal, it was a geopolitical
operation. Webb's investigation revealed a deep
connection between Ross's supplier, Danilo Blandon,
and the CIA. The core allegation was that the
CIA was effectively sponsoring, or at the very
least turning a blind eye to, this cocaine importation
specifically to fund the Contras in Nicaragua.
The Iran -Contra affair. Just as a quick refresher
for everyone, the U .S. government was supporting
the Contras, which was a rebel group fighting
the socialist government in Nicaragua. But Congress
had officially cut off their funding. Correct.
So the theory, and what Webb reported in his
series, was that the massive profits from the
crack epidemic in Los Angeles were being funneled
back to buy weapons for the Contra War. Blandon
wasn't just a drug dealer, he was actively raising
war funds. Now we need to add the nuance here.
This is a highly disputed claim. The major national
newspapers came after Webb's reporting hard.
It is very nuanced. Webb alleged that this intelligence
connection gave Ross a level of protection. That
the federal spooks kept the local heat off his
back. That specific claim has been heavily disputed
by many, and the CIA obviously denied it in their
internal investigations. However, the factual
connection between Ross's suppliers and the Contra
movement is a documented key part of the narrative.
Blandon absolutely was a Contra supporter. So
whether Ross knew he was a pawn in a larger geopolitical
game or if he was just a guy buying really cheap
product, that is the subject of endless debate.
It is, but it adds a very dark layer to the story.
The idea that the devastation in American cities
might have been considered acceptable collateral
damage for foreign policy. Right. It raises the
question of whether the government allowed crack
to flood LA to fight communism in Central America.
And even if the answer to that is a strict no,
the fact that the question even exists shows
just how deep Ross's operation went. It's a lot
to wrap your head around. But while all this
political swirling is happening, Ross's luck
eventually runs out. You simply can't run a billion
dollar illegal enterprise forever. It always
comes crashing down. The fall happened in 1996.
And ironically, he was taken down by the very
source who helped build him up in the first place.
A sting operation. Yes. Blandon had actually
been arrested earlier. And to save his own skin
and to get a reduced sentence, he became an informant
for the DEA. He set Ross up. Wow. Ross was convicted
of purchasing 100 kilograms of cocaine from a
federal agent in a setup orchestrated entirely
by Blandon. Talk about betrayal. And this was
right during the era of the three strikes laws,
right? The crime bills were incredibly tough
back then. Exactly. Because Ross had two prior
convictions, even though they were relatively
minor compared to this massive hundred kilo deal,
this new conviction triggered the mandatory life
sentence. He was sentenced to life imprisonment
without the possibility of parole. That was supposed
to be the end of the story. Rick Ross dies in
federal prison. But this is where the story takes
its most surprising turn. We started this deep
dive by saying he dropped out of high school
because he couldn't read. And at age 28, during
his first stint in prison before the life sentence
came down, he finally learned. He realized that
if he couldn't read, he was always going to be
at the mercy of others. The lawyers, the snitches,
the justice system. So he spent his time behind
bars, not just lifting weights or passing time,
but really studying. He started with the absolute
basics. Exactly. And once he could read, he went
straight to the prison law library. Talk about
a pivot. He goes from being an illiterate kingpin
to a jailhouse lawyer. And he was highly effective
at it. He didn't just casually read the law.
He understood the mechanics of it. He found a
legal loophole in his own case. What did he find?
He discovered that the three strikes law had
been erroneously applied in his specific case.
His prior convictions didn't actually qualify
under the strict federal definitions the way
the prosecutors had claimed they did. Wait, so
he essentially represented himself. He did the
primary research. He filed the motions and the
court actually agreed with him. A federal court
of appeals ordered him to be resentenced. His
life sentence was reduced to 20 years. That is
just incredible. He literally read his way. to
freedom. He was released on September 29, 2009.
It's a massive testament to the idea that knowledge
really is power. If he hadn't learned to read
in that cell, he would still be in a cage today,
or he might have passed away in prison. So he
gets out in 2009, but he steps into a world where
his name is already famous, but not because of
him. Right. While he was sitting in prison, a
former Corrections officer turned rapper, named
William Leonard Roberts II, started using the
stage name Rick Ross. And he adopted the whole
persona, the beard, the sunglasses, the drug
kingpin image. He was rapping about the exact
life Freeway Rick actually lived. Yes. And Freeway
Ricky was not happy about it. He felt his identity
was being stolen and monetized by someone else.
So in 2010, shortly after his release, he filed
a copyright infringement lawsuit against the
rapper. He wanted $10 million for the use of
his name and image. This was a huge deal in the
hip hop world. I remember Jay -Z was even called
to testify during the proceedings because he
was the president of Def Jam at the time the
rapper was signed. It was a major legal battle.
But ultimately, Freeway Rick lost. The courts
ruled in favor of the rapper. On what grounds?
It seems like a pretty clear -cut case of identity
theft. I mean, the guy is literally using his
name and his life story. It came down to First
Amendment grounds. The court ruled that the rapper's
music and persona were what they call transformative.
They essentially said that the Rick Ross rap
persona was a fictional character a valid artistic
expression, even if it borrowed heavily from
reality. Because the rapper added original music
and created a character out of it, it was protected
speech. Right. The case went through both federal
and state courts, but the dismissal was ultimately
upheld. That has to be so frustrating. You serve
the time, you finally get out, and someone else
is making millions off your name and reputation,
and the courts just say, well, it's art. It certainly
was a massive point of contention for him, but
Ross didn't let it stop him. He's incredibly
resilient. Since his release, he's been surprisingly
active in legitimate business. He's been working
hard to reclaim his own brand. What is he up
to now? Well, he's leaned heavily into entrepreneurship,
but legally this time. In 2022, he started a
boxing management company called Team Freeway
Boxing. Oh, interesting. Yeah, he's got professional
fighters under contract. He says boxing world
is actually a lot like the drug game. You have
to spot talent early and protect your investment.
And I saw something in the sources about cannabis.
Yes. In a 24 interview, he stated he owns a marijuana
dispensary, which is a fascinating shift, if
you think about it, going from illicit cocaine,
which ravaged communities, to legal cannabis,
which is now a heavily regulated tax generating
industry. It really mirrors the changing legal
landscape of the whole country. Absolutely. And
he's an author, too. He co -wrote his autobiography
with Cathy Scott. It was actually nominated for
an award, the Forward Review's Indie Fab Best
Book of the Year in the True Crime category.
He clearly wants to make sure his version of
the story is the one people actually remember.
He's definitely managed to stay in the public
eye, though not always entirely without trouble.
There was that incident back in 2015. Right,
the traffic stop. Police pulled him over and
found $100 ,000 in cash in his car. Which, given
his very well -known history, Looks pretty suspicious.
If I'm a cop and I pull over freeway Rick Ross
and he has a duffel bag of cash in the trunk.
It definitely looks bad. But Royce claimed racial
profiling. He said the money was purely from
legitimate book sales and speaking fees and that
he was carrying it because he was going to buy
a home. And here's the most important thing.
Ultimately, the charges were completely dropped.
They couldn't prove it was drug money, which
suggests his story held up under scrutiny. It
seems he really is trying to walk the straight
and narrow path now. And pop culture still loves
him. If you watch the television show Snowfall,
the main character Franklin Saint is heavily,
heavily influenced by Ross's life. Ross actually
claims he partnered with the show's creator,
John Singleton, to make a movie way before the
show was ever created. He says Singleton disappeared
on him and then suddenly Snowfall came out. It's
another instance where Ross feels his life story
was used without his full participation or compensation,
though Singleton passed away before anyone could
fully confirm that exact account. It seems like
a recurring theme for him, his life story being
a commodity that everyone else wants to sell.
It really is. But you have to give him credit
for his sheer resilience. He went from a high
school dropout who couldn't read to running a
billion dollar enterprise, albeit a highly illegal
one, to facing a life sentence in federal prison,
to walking out a free man running legal businesses.
It really brings us back to that central irony
we started with at the top of the show. Here's
a guy who was denied a tennis scholarship because
the system completely failed to teach him to
read. He builds an empire based on complex math
and logistics, but nearly loses his life to it.
And the only thing that saves his life in the
end is finally getting the basic education he
should have had in the first place. It circles
back perfectly. Yeah. The literacy that denied
him his first dream is the exact thing that allowed
him to have a second life. So let's zoom out
for a second. What does this all mean for us?
Why does the story of freeway Rick Ross matter
to you today other than just being a crazy crime
thriller? I think it forces us to look deeply
at the concept of talent versus opportunity.
Ross clearly had immense natural talent. He had
organizational skills, strategic vision, and
the ability to lead a massive workforce. Those
are Fortune 500 CEO level traits. He understood
supply and demand instinctively. Absolutely.
If he had been born in a different zip code,
or if a teacher had caught that reading disability
in the second grade, maybe he's running a massive
logistics company like FedEx or managing a billion
-dollar hedge fund today. Exactly. We lost a
potential business leader to the streets. And
that raises a really provocative question for
you, the listener, to mull over. If the educational
system hadn't failed Ross on that high school
tennis scholarship, Would the crack epidemic
in L .A. have looked completely different? Or
was the market force of cheap cocaine so overwhelmingly
strong that it was simply inevitable, regardless
of who was running the logistics? Was he the
grand architect of the disaster or just the guy
who happened to be standing there when the floodgates
opened? That is definitely something to chew
on. It challenges how we look at history. Great
men or great forces. In this case, it might just
be a bit of both. Well, thanks for joining us
on this deep dive into the real Rick Ross. It's
a story that challenges a lot of assumptions
about crime, literacy, and redemption. Always
a pleasure to dig into the details with you.
We'll catch you on the next one. Stay curious.