WEBVTT 00:00:00.000 --> 00:00:05.280 OK, so let's unpack this. We hear a lot of stories 00:00:05.280 --> 00:00:07.379 about the American dream. Oh, absolutely. You 00:00:07.379 --> 00:00:08.580 know, the whole idea that you start with nothing. 00:00:08.919 --> 00:00:11.000 You pull yourself up by your bootstraps and you 00:00:11.000 --> 00:00:13.519 build this massive empire. The classic narrative. 00:00:13.740 --> 00:00:15.859 Exactly. But usually when we talk about that, 00:00:16.300 --> 00:00:19.239 we are talking about, I don't know, tech startups 00:00:19.239 --> 00:00:22.379 in a garage or real estate moguls in Manhattan. 00:00:22.640 --> 00:00:24.440 Yeah, we definitely aren't usually talking about 00:00:24.440 --> 00:00:28.000 a guy who at his absolute peak was pulling in 00:00:28.000 --> 00:00:32.299 three million dollars a day. A day. Yes. Three 00:00:32.299 --> 00:00:35.780 million a day selling drugs. And doing it all 00:00:35.780 --> 00:00:37.920 while being functionally illiterate. That is 00:00:37.920 --> 00:00:40.020 the part that always gets me. He couldn't even 00:00:40.020 --> 00:00:42.240 read the street signs on the very freeway he 00:00:42.240 --> 00:00:46.000 was named after. It's wild. So today we are doing 00:00:46.000 --> 00:00:49.460 a deep dive into the life of Ricky Donald Ross. 00:00:49.579 --> 00:00:51.380 And I want to stop you right there if you're 00:00:51.380 --> 00:00:52.719 listening because I know exactly what you're 00:00:52.719 --> 00:00:55.500 thinking. You're picturing the rapper. Right. 00:00:56.000 --> 00:00:57.780 You're picturing the guy with the big beard, 00:00:57.939 --> 00:01:00.740 the sunglasses, shouting Maybach music on the 00:01:00.740 --> 00:01:03.539 radio. And that is a very, very common point 00:01:03.539 --> 00:01:06.299 of confusion. But the man we are talking about 00:01:06.299 --> 00:01:09.000 today is the actual inspiration for that name. 00:01:09.200 --> 00:01:11.840 Yeah. We are diving into the source material 00:01:11.840 --> 00:01:15.000 surrounding the real freeway Rick Ross, the man 00:01:15.000 --> 00:01:17.079 who, according to estimates from our sources, 00:01:17.319 --> 00:01:21.340 grossed over 900 million dollars in the 1980s, 00:01:21.379 --> 00:01:25.409 which if we. If we run the inflation calculator 00:01:25.409 --> 00:01:28.549 to adjust for 2025 numbers, that sits somewhere 00:01:28.549 --> 00:01:32.650 around $2 .7 billion. It's staggering. Staggering 00:01:32.650 --> 00:01:34.930 wealth. I mean, that is Forbes list territory, 00:01:35.150 --> 00:01:37.629 but completely off the books. It is. But what 00:01:37.629 --> 00:01:40.329 makes this deep dive so compelling, looking through 00:01:40.329 --> 00:01:42.310 all these documents and reports, isn't just the 00:01:42.310 --> 00:01:44.769 money. Right. It's the sheer contradictions of 00:01:44.769 --> 00:01:48.209 his life. We have a man who was a central figure 00:01:48.209 --> 00:01:51.489 in the US crack Copain epidemic, who became linked 00:01:51.489 --> 00:01:55.159 to a massive CIA. scandal and yet his entire 00:01:55.159 --> 00:01:57.859 criminal career essentially started because of 00:01:57.859 --> 00:02:00.400 a massive failure in the public education system. 00:02:00.459 --> 00:02:02.900 Yeah the education piece is huge and then his 00:02:02.900 --> 00:02:05.340 exit from prison that only happened because he 00:02:05.340 --> 00:02:07.439 taught himself to read after he was already locked 00:02:07.439 --> 00:02:09.840 up for life. It really is a wild ride. So let's 00:02:09.840 --> 00:02:11.620 go back to the beginning to figure out how this 00:02:11.620 --> 00:02:14.719 happened. Before he was a kingpin Ricky Ross 00:02:14.719 --> 00:02:17.900 was just a kid at Susan Miller Dorsey High School 00:02:17.900 --> 00:02:20.280 in Los Angeles. Right. And here's the kicker. 00:02:20.560 --> 00:02:23.340 He wasn't trying to be a criminal. He wasn't 00:02:23.340 --> 00:02:25.860 out there looking for a hustle. He was actually 00:02:25.860 --> 00:02:28.259 trying to be a tennis player. And by all accounts 00:02:28.259 --> 00:02:30.879 in the sources, he was a phenom. He wasn't just 00:02:30.879 --> 00:02:33.259 good for a high schooler. He was actively being 00:02:33.259 --> 00:02:36.419 scouted. Wow. He had real hopes for a college 00:02:36.419 --> 00:02:39.360 scholarship. Tennis was supposed to be his ticket 00:02:39.360 --> 00:02:42.280 out of South Central L .A. But this is where 00:02:42.280 --> 00:02:44.439 we hit that sliding doors moment. The barrier. 00:02:44.879 --> 00:02:47.830 Precisely. He was illiterate. He had gone through 00:02:47.830 --> 00:02:50.569 nearly 12 years of public schooling, and he still 00:02:50.569 --> 00:02:53.009 couldn't read or write. That's just a colossal 00:02:53.009 --> 00:02:55.229 failure by the schools. Totally. He was relying 00:02:55.229 --> 00:02:58.169 on charm, a good memory, and his athletic ability 00:02:58.169 --> 00:03:01.090 just to get by day to day. But when the colleges 00:03:01.090 --> 00:03:03.469 actually found out about his reading level, the 00:03:03.469 --> 00:03:05.590 scholarship offers were reneged immediately. 00:03:05.969 --> 00:03:08.110 You just have to imagine that psychological blow. 00:03:08.330 --> 00:03:10.870 You know, you have a path, you have a talent, 00:03:11.210 --> 00:03:13.610 and the system fails to teach you the absolute 00:03:13.610 --> 00:03:16.349 basics. Suddenly that door just slams shut in 00:03:16.349 --> 00:03:18.129 your face. And he dropped out of high school 00:03:18.129 --> 00:03:20.169 just weeks before graduation because he knew 00:03:20.169 --> 00:03:22.250 he wasn't going to get the diploma anyway. So 00:03:22.250 --> 00:03:25.509 now you have a young man with ambition, but no 00:03:25.509 --> 00:03:28.849 degree, no reading skills, and no scholarship. 00:03:29.949 --> 00:03:33.310 He's drifting. Right. And this is where you'd 00:03:33.310 --> 00:03:36.240 expect the movie script to kick in. Like, He 00:03:36.240 --> 00:03:38.340 meets a cartel boss in a dark alley or something. 00:03:38.340 --> 00:03:41.560 A total Scarface moment. Exactly. Yeah. But it's 00:03:41.560 --> 00:03:43.280 actually much more mundane, which I think makes 00:03:43.280 --> 00:03:45.840 it way more interesting. He didn't meet a cartel 00:03:45.840 --> 00:03:48.639 leader. He met an upholstery teacher. Wait, an 00:03:48.639 --> 00:03:51.319 upholstery teacher, like fixing couches. Yes, 00:03:51.400 --> 00:03:53.659 literally fixing furniture. Ross was hanging 00:03:53.659 --> 00:03:55.900 around a local trade school or community college 00:03:55.900 --> 00:03:58.020 just trying to figure out his next move. And 00:03:58.020 --> 00:04:00.060 this upholstery teacher he befriended revealed 00:04:00.060 --> 00:04:03.319 that he dealt cocaine on the side. Wow. Yeah. 00:04:03.319 --> 00:04:06.360 And he offered Ross a small amount to sell. That 00:04:06.360 --> 00:04:08.939 is just, you really can't make that up. The banality 00:04:08.939 --> 00:04:12.120 of evil, right? So Ross takes this small amount, 00:04:12.319 --> 00:04:15.099 he sells it, and then he uses the profit to buy 00:04:15.099 --> 00:04:17.819 more, and just keeps flipping it. He's basically 00:04:17.819 --> 00:04:20.199 applying basic business principles. Well, compounding 00:04:20.199 --> 00:04:21.980 interest, essentially. Right, compounding interest, 00:04:22.379 --> 00:04:25.240 but just to... a highly illegal product. And 00:04:25.240 --> 00:04:27.480 he was incredibly good at it. He had a natural 00:04:27.480 --> 00:04:29.839 mind for numbers, even if he couldn't read the 00:04:29.839 --> 00:04:32.319 words on a page. He quickly outgrew the teacher 00:04:32.319 --> 00:04:34.379 supply. So this is where he starts climbing the 00:04:34.379 --> 00:04:37.220 ladder. Exactly. The teacher introduces him to 00:04:37.220 --> 00:04:39.680 his own supplier, a man named Ivan Arguelles. 00:04:40.100 --> 00:04:42.540 This connected Ross to larger quantities and 00:04:42.540 --> 00:04:45.379 much better prices. He went from dealing grams 00:04:45.379 --> 00:04:48.759 to dealing ounces. But the drug trade isn't exactly 00:04:48.759 --> 00:04:51.100 a stable corporate environment. People get hurt. 00:04:51.240 --> 00:04:53.769 No, it is not. About eight months into this, 00:04:53.970 --> 00:04:57.050 Arguelles is shot in the spine. Man. He survives, 00:04:57.209 --> 00:04:59.269 but he's hospitalized and effectively out of 00:04:59.269 --> 00:05:02.550 the game. So the business shifts over to Arguelles' 00:05:02.810 --> 00:05:04.730 brother -in -law, a guy named Henry Corrales. 00:05:04.850 --> 00:05:07.410 Okay. But Corrales didn't really have the stomach 00:05:07.410 --> 00:05:09.689 for the violence and the risk that comes with 00:05:09.689 --> 00:05:13.060 the trade. And this right here. based on all 00:05:13.060 --> 00:05:15.540 the sources, is the moment that changes everything. 00:05:15.560 --> 00:05:18.720 Yeah. Because Corrales introduces Ross to a contact 00:05:18.720 --> 00:05:21.420 who would catapult him from a local LA dealer 00:05:21.420 --> 00:05:24.660 to a national figure. Enter Danilo Blandon. If 00:05:24.660 --> 00:05:26.800 you study the history of narcotics in America, 00:05:27.399 --> 00:05:30.000 Blandon is a massive, pivotal figure. Right. 00:05:30.160 --> 00:05:32.860 He was in Nicaraguan exile. He wasn't a street 00:05:32.860 --> 00:05:35.420 dealer. He was highly educated. He had a master's 00:05:35.420 --> 00:05:38.060 degree in marketing. And he was part of a major 00:05:38.060 --> 00:05:41.120 political movement. He saw the sheer volume that 00:05:41.120 --> 00:05:44.019 Ross was moving and was highly impressed. So 00:05:44.019 --> 00:05:46.519 when Corrales retired, Ross just started dealing 00:05:46.519 --> 00:05:49.379 directly with Blandon. Exactly. And this relationship 00:05:49.379 --> 00:05:51.360 is crucial because of the economics involved. 00:05:52.139 --> 00:05:53.860 We need to geek out on the numbers for a second 00:05:53.860 --> 00:05:56.420 here because this is where Freeway Rick Ross 00:05:56.420 --> 00:05:58.779 really changes the game. It wasn't just about 00:05:58.779 --> 00:06:00.560 selling drugs. It was about the price point. 00:06:00.720 --> 00:06:03.649 This is a classic supply chain advantage. Through 00:06:03.649 --> 00:06:06.550 Blandon and Blandon's own supplier, Noren Menises 00:06:06.550 --> 00:06:09.310 -Cantarero, Ross was suddenly getting Nicaraguan 00:06:09.310 --> 00:06:11.930 cocaine at significantly reduced rates. He cut 00:06:11.930 --> 00:06:14.230 out all the local middlemen. We see this in legitimate 00:06:14.230 --> 00:06:16.550 business all the time. If you can get your cost 00:06:16.550 --> 00:06:19.410 of goods sold down, you can undercut the entire 00:06:19.410 --> 00:06:21.589 competition. It's basically the Walmart model. 00:06:21.689 --> 00:06:24.329 And he executed that aggressively. At the time, 00:06:24.470 --> 00:06:27.970 cocaine was mostly a rich man's drug. A kilo 00:06:27.970 --> 00:06:30.889 of powder cocaine could cost as much as $60 ,000. 00:06:31.029 --> 00:06:33.889 It was highly exclusive. Yeah. But Ross was able 00:06:33.889 --> 00:06:36.870 to drop that price down to as low as $10 ,000. 00:06:37.069 --> 00:06:40.110 Wow. From 60 grand to 10 grand. That's an 83 00:06:40.110 --> 00:06:43.529 % price cut. That effectively collapses the existing 00:06:43.529 --> 00:06:46.529 market. And that massive price drop is exactly 00:06:46.529 --> 00:06:48.850 what allowed the market to expand so violently. 00:06:49.500 --> 00:06:52.339 It made the drug accessible to street gangs, 00:06:52.839 --> 00:06:55.220 specifically the Bloods and the Crips, who previously 00:06:55.220 --> 00:06:56.879 just couldn't afford that kind of volume. Right, 00:06:56.920 --> 00:06:58.560 because now they could buy it cheap, cook it 00:06:58.560 --> 00:07:00.240 into crack, and sell it for a few dollars a hit. 00:07:00.500 --> 00:07:03.990 Exactly. He wasn't just selling to elite wealthy 00:07:03.990 --> 00:07:07.509 users anymore. He was democratizing the supply, 00:07:07.649 --> 00:07:10.269 for lack of a better word. And the volume was 00:07:10.269 --> 00:07:12.850 just insane. The sources say he was purchasing 00:07:12.850 --> 00:07:17.069 a thousand pounds as 454 kilos of cocaine every 00:07:17.069 --> 00:07:19.910 single week. And selling up to three million 00:07:19.910 --> 00:07:22.550 dollars in a single day. That's where the freeway 00:07:22.550 --> 00:07:24.930 name comes from, right? It wasn't because he 00:07:24.930 --> 00:07:27.230 was fast on the tennis court. It was because 00:07:27.230 --> 00:07:29.509 he owned properties all along the Harbor Freeway 00:07:29.509 --> 00:07:31.930 Interstate 110 in Los Angeles. That's right. 00:07:31.990 --> 00:07:35.209 It was a massive logistics network. And despite 00:07:35.209 --> 00:07:37.970 his illiteracy, the operation was incredibly 00:07:37.970 --> 00:07:40.250 sophisticated. They were using tech, right? Oh, 00:07:40.310 --> 00:07:43.129 yeah. They used police scanners, voice scramblers. 00:07:43.670 --> 00:07:45.829 They were often technically ahead of the law 00:07:45.829 --> 00:07:47.589 enforcement agencies that were trying to catch 00:07:47.589 --> 00:07:50.050 them. There's actually a quote from a Los Angeles 00:07:50.050 --> 00:07:53.069 county sheriff who admitted Ross's men had better 00:07:53.069 --> 00:07:56.089 equipment than the police had. I love the detail 00:07:56.089 --> 00:07:57.850 in the source material about how they handled 00:07:57.850 --> 00:07:59.980 the money, though. They're making millions of 00:07:59.980 --> 00:08:02.720 dollars. But Ross is absolutely terrified his 00:08:02.720 --> 00:08:04.639 mother is going to find out. It's such a human 00:08:04.639 --> 00:08:07.000 element in the middle of this massive criminal 00:08:07.000 --> 00:08:09.939 enterprise. Yeah. In a jailhouse interview later 00:08:09.939 --> 00:08:12.560 on, he admitted they were investing in houses 00:08:12.560 --> 00:08:15.139 and legitimate businesses, partly just to hide 00:08:15.139 --> 00:08:17.220 the cash from their mothers so they wouldn't 00:08:17.220 --> 00:08:19.720 see them spending lavishly. Because you can't 00:08:19.720 --> 00:08:22.000 exactly just leave a giant pile of cash in your 00:08:22.000 --> 00:08:24.579 mom's living room. Right. And speaking of investments, 00:08:25.100 --> 00:08:27.379 didn't he put money into Anita Baker's first 00:08:27.379 --> 00:08:30.579 album? He did. A portion of his proceeds went 00:08:30.579 --> 00:08:33.779 into funding that album. It really shows these 00:08:33.779 --> 00:08:36.039 strange intersections between the underworld 00:08:36.039 --> 00:08:39.019 and legitimate pop culture. The crack epidemic 00:08:39.019 --> 00:08:42.200 proceeds were inadvertently funding smooth R 00:08:42.200 --> 00:08:45.620 &B. Exactly. Okay, so we have the rise of the 00:08:45.620 --> 00:08:48.340 empire. But we have to talk about the controversy. 00:08:48.980 --> 00:08:51.480 Because you mentioned Danilo Bland and the Nicaraguan 00:08:51.480 --> 00:08:56.000 exile. This leads us to one of the most explosive 00:08:56.000 --> 00:08:58.799 political scandals of the 90s. The Dark Alliance. 00:08:59.139 --> 00:09:01.799 Yes. This is where the story gets really heavy. 00:09:02.080 --> 00:09:03.779 For you listening, we want to be clear that we 00:09:03.779 --> 00:09:05.720 are just reporting what the sources outline here, 00:09:05.740 --> 00:09:09.139 not taking any political sides. In 1996, a journalist 00:09:09.139 --> 00:09:11.720 named Gary Webb wrote a series for the San Jose 00:09:11.720 --> 00:09:14.440 Mercury News. Right. And he alleged that this 00:09:14.440 --> 00:09:17.059 wasn't just a simple drug deal, it was a geopolitical 00:09:17.059 --> 00:09:20.019 operation. Webb's investigation revealed a deep 00:09:20.019 --> 00:09:23.740 connection between Ross's supplier, Danilo Blandon, 00:09:23.879 --> 00:09:27.240 and the CIA. The core allegation was that the 00:09:27.240 --> 00:09:29.879 CIA was effectively sponsoring, or at the very 00:09:29.879 --> 00:09:33.179 least turning a blind eye to, this cocaine importation 00:09:33.179 --> 00:09:36.399 specifically to fund the Contras in Nicaragua. 00:09:36.559 --> 00:09:39.559 The Iran -Contra affair. Just as a quick refresher 00:09:39.559 --> 00:09:42.080 for everyone, the U .S. government was supporting 00:09:42.080 --> 00:09:44.480 the Contras, which was a rebel group fighting 00:09:44.480 --> 00:09:47.200 the socialist government in Nicaragua. But Congress 00:09:47.200 --> 00:09:49.360 had officially cut off their funding. Correct. 00:09:49.639 --> 00:09:52.159 So the theory, and what Webb reported in his 00:09:52.159 --> 00:09:54.600 series, was that the massive profits from the 00:09:54.600 --> 00:09:57.019 crack epidemic in Los Angeles were being funneled 00:09:57.019 --> 00:10:00.320 back to buy weapons for the Contra War. Blandon 00:10:00.320 --> 00:10:02.759 wasn't just a drug dealer, he was actively raising 00:10:02.759 --> 00:10:04.879 war funds. Now we need to add the nuance here. 00:10:05.220 --> 00:10:07.879 This is a highly disputed claim. The major national 00:10:07.879 --> 00:10:10.039 newspapers came after Webb's reporting hard. 00:10:10.220 --> 00:10:12.840 It is very nuanced. Webb alleged that this intelligence 00:10:12.840 --> 00:10:15.320 connection gave Ross a level of protection. That 00:10:15.320 --> 00:10:17.679 the federal spooks kept the local heat off his 00:10:17.679 --> 00:10:20.600 back. That specific claim has been heavily disputed 00:10:20.600 --> 00:10:23.460 by many, and the CIA obviously denied it in their 00:10:23.460 --> 00:10:26.740 internal investigations. However, the factual 00:10:26.740 --> 00:10:29.639 connection between Ross's suppliers and the Contra 00:10:29.639 --> 00:10:33.039 movement is a documented key part of the narrative. 00:10:33.879 --> 00:10:36.759 Blandon absolutely was a Contra supporter. So 00:10:36.759 --> 00:10:40.200 whether Ross knew he was a pawn in a larger geopolitical 00:10:40.200 --> 00:10:42.860 game or if he was just a guy buying really cheap 00:10:42.860 --> 00:10:45.899 product, that is the subject of endless debate. 00:10:46.190 --> 00:10:49.269 It is, but it adds a very dark layer to the story. 00:10:49.529 --> 00:10:52.289 The idea that the devastation in American cities 00:10:52.289 --> 00:10:54.289 might have been considered acceptable collateral 00:10:54.289 --> 00:10:56.669 damage for foreign policy. Right. It raises the 00:10:56.669 --> 00:10:58.450 question of whether the government allowed crack 00:10:58.450 --> 00:11:01.710 to flood LA to fight communism in Central America. 00:11:02.149 --> 00:11:04.070 And even if the answer to that is a strict no, 00:11:04.429 --> 00:11:06.210 the fact that the question even exists shows 00:11:06.210 --> 00:11:08.710 just how deep Ross's operation went. It's a lot 00:11:08.710 --> 00:11:10.549 to wrap your head around. But while all this 00:11:10.549 --> 00:11:12.529 political swirling is happening, Ross's luck 00:11:12.529 --> 00:11:15.549 eventually runs out. You simply can't run a billion 00:11:15.549 --> 00:11:17.850 dollar illegal enterprise forever. It always 00:11:17.850 --> 00:11:21.600 comes crashing down. The fall happened in 1996. 00:11:22.899 --> 00:11:25.419 And ironically, he was taken down by the very 00:11:25.419 --> 00:11:27.340 source who helped build him up in the first place. 00:11:27.539 --> 00:11:30.279 A sting operation. Yes. Blandon had actually 00:11:30.279 --> 00:11:33.539 been arrested earlier. And to save his own skin 00:11:33.539 --> 00:11:36.759 and to get a reduced sentence, he became an informant 00:11:36.759 --> 00:11:41.659 for the DEA. He set Ross up. Wow. Ross was convicted 00:11:41.659 --> 00:11:44.679 of purchasing 100 kilograms of cocaine from a 00:11:44.679 --> 00:11:47.740 federal agent in a setup orchestrated entirely 00:11:47.740 --> 00:11:50.259 by Blandon. Talk about betrayal. And this was 00:11:50.259 --> 00:11:52.220 right during the era of the three strikes laws, 00:11:52.600 --> 00:11:54.799 right? The crime bills were incredibly tough 00:11:54.799 --> 00:11:57.840 back then. Exactly. Because Ross had two prior 00:11:57.840 --> 00:11:59.799 convictions, even though they were relatively 00:11:59.799 --> 00:12:02.379 minor compared to this massive hundred kilo deal, 00:12:02.940 --> 00:12:05.259 this new conviction triggered the mandatory life 00:12:05.259 --> 00:12:07.799 sentence. He was sentenced to life imprisonment 00:12:07.799 --> 00:12:09.820 without the possibility of parole. That was supposed 00:12:09.820 --> 00:12:12.379 to be the end of the story. Rick Ross dies in 00:12:12.379 --> 00:12:14.480 federal prison. But this is where the story takes 00:12:14.480 --> 00:12:17.440 its most surprising turn. We started this deep 00:12:17.440 --> 00:12:19.100 dive by saying he dropped out of high school 00:12:19.100 --> 00:12:22.250 because he couldn't read. And at age 28, during 00:12:22.250 --> 00:12:24.529 his first stint in prison before the life sentence 00:12:24.529 --> 00:12:27.649 came down, he finally learned. He realized that 00:12:27.649 --> 00:12:29.649 if he couldn't read, he was always going to be 00:12:29.649 --> 00:12:32.690 at the mercy of others. The lawyers, the snitches, 00:12:32.850 --> 00:12:35.769 the justice system. So he spent his time behind 00:12:35.769 --> 00:12:38.429 bars, not just lifting weights or passing time, 00:12:38.789 --> 00:12:41.450 but really studying. He started with the absolute 00:12:41.450 --> 00:12:45.850 basics. Exactly. And once he could read, he went 00:12:45.850 --> 00:12:48.330 straight to the prison law library. Talk about 00:12:48.330 --> 00:12:51.129 a pivot. He goes from being an illiterate kingpin 00:12:51.129 --> 00:12:53.929 to a jailhouse lawyer. And he was highly effective 00:12:53.929 --> 00:12:56.330 at it. He didn't just casually read the law. 00:12:56.429 --> 00:12:59.529 He understood the mechanics of it. He found a 00:12:59.529 --> 00:13:01.789 legal loophole in his own case. What did he find? 00:13:01.960 --> 00:13:04.139 He discovered that the three strikes law had 00:13:04.139 --> 00:13:07.000 been erroneously applied in his specific case. 00:13:07.539 --> 00:13:09.600 His prior convictions didn't actually qualify 00:13:09.600 --> 00:13:11.820 under the strict federal definitions the way 00:13:11.820 --> 00:13:14.200 the prosecutors had claimed they did. Wait, so 00:13:14.200 --> 00:13:16.340 he essentially represented himself. He did the 00:13:16.340 --> 00:13:18.480 primary research. He filed the motions and the 00:13:18.480 --> 00:13:20.639 court actually agreed with him. A federal court 00:13:20.639 --> 00:13:23.360 of appeals ordered him to be resentenced. His 00:13:23.360 --> 00:13:26.080 life sentence was reduced to 20 years. That is 00:13:26.080 --> 00:13:29.059 just incredible. He literally read his way. to 00:13:29.059 --> 00:13:32.779 freedom. He was released on September 29, 2009. 00:13:33.679 --> 00:13:36.120 It's a massive testament to the idea that knowledge 00:13:36.120 --> 00:13:38.879 really is power. If he hadn't learned to read 00:13:38.879 --> 00:13:41.299 in that cell, he would still be in a cage today, 00:13:41.419 --> 00:13:43.279 or he might have passed away in prison. So he 00:13:43.279 --> 00:13:47.519 gets out in 2009, but he steps into a world where 00:13:47.519 --> 00:13:50.320 his name is already famous, but not because of 00:13:50.320 --> 00:13:53.279 him. Right. While he was sitting in prison, a 00:13:53.279 --> 00:13:55.820 former Corrections officer turned rapper, named 00:13:55.820 --> 00:13:58.850 William Leonard Roberts II, started using the 00:13:58.850 --> 00:14:01.710 stage name Rick Ross. And he adopted the whole 00:14:01.710 --> 00:14:04.789 persona, the beard, the sunglasses, the drug 00:14:04.789 --> 00:14:07.250 kingpin image. He was rapping about the exact 00:14:07.250 --> 00:14:10.450 life Freeway Rick actually lived. Yes. And Freeway 00:14:10.450 --> 00:14:12.809 Ricky was not happy about it. He felt his identity 00:14:12.809 --> 00:14:15.029 was being stolen and monetized by someone else. 00:14:15.210 --> 00:14:18.330 So in 2010, shortly after his release, he filed 00:14:18.330 --> 00:14:20.429 a copyright infringement lawsuit against the 00:14:20.429 --> 00:14:23.309 rapper. He wanted $10 million for the use of 00:14:23.309 --> 00:14:25.799 his name and image. This was a huge deal in the 00:14:25.799 --> 00:14:28.240 hip hop world. I remember Jay -Z was even called 00:14:28.240 --> 00:14:30.539 to testify during the proceedings because he 00:14:30.539 --> 00:14:32.480 was the president of Def Jam at the time the 00:14:32.480 --> 00:14:34.860 rapper was signed. It was a major legal battle. 00:14:35.600 --> 00:14:39.320 But ultimately, Freeway Rick lost. The courts 00:14:39.320 --> 00:14:42.379 ruled in favor of the rapper. On what grounds? 00:14:42.419 --> 00:14:45.080 It seems like a pretty clear -cut case of identity 00:14:45.080 --> 00:14:47.320 theft. I mean, the guy is literally using his 00:14:47.320 --> 00:14:50.240 name and his life story. It came down to First 00:14:50.240 --> 00:14:53.019 Amendment grounds. The court ruled that the rapper's 00:14:53.019 --> 00:14:56.000 music and persona were what they call transformative. 00:14:56.820 --> 00:14:58.559 They essentially said that the Rick Ross rap 00:14:58.559 --> 00:15:02.120 persona was a fictional character a valid artistic 00:15:02.120 --> 00:15:04.580 expression, even if it borrowed heavily from 00:15:04.580 --> 00:15:07.519 reality. Because the rapper added original music 00:15:07.519 --> 00:15:10.080 and created a character out of it, it was protected 00:15:10.080 --> 00:15:12.659 speech. Right. The case went through both federal 00:15:12.659 --> 00:15:15.500 and state courts, but the dismissal was ultimately 00:15:15.500 --> 00:15:18.279 upheld. That has to be so frustrating. You serve 00:15:18.279 --> 00:15:20.240 the time, you finally get out, and someone else 00:15:20.240 --> 00:15:22.360 is making millions off your name and reputation, 00:15:22.360 --> 00:15:24.980 and the courts just say, well, it's art. It certainly 00:15:24.980 --> 00:15:28.559 was a massive point of contention for him, but 00:15:28.559 --> 00:15:31.710 Ross didn't let it stop him. He's incredibly 00:15:31.710 --> 00:15:35.250 resilient. Since his release, he's been surprisingly 00:15:35.250 --> 00:15:37.929 active in legitimate business. He's been working 00:15:37.929 --> 00:15:40.669 hard to reclaim his own brand. What is he up 00:15:40.669 --> 00:15:43.830 to now? Well, he's leaned heavily into entrepreneurship, 00:15:44.549 --> 00:15:47.809 but legally this time. In 2022, he started a 00:15:47.809 --> 00:15:50.370 boxing management company called Team Freeway 00:15:50.370 --> 00:15:53.309 Boxing. Oh, interesting. Yeah, he's got professional 00:15:53.309 --> 00:15:56.289 fighters under contract. He says boxing world 00:15:56.289 --> 00:15:58.519 is actually a lot like the drug game. You have 00:15:58.519 --> 00:16:00.639 to spot talent early and protect your investment. 00:16:01.019 --> 00:16:03.200 And I saw something in the sources about cannabis. 00:16:03.559 --> 00:16:07.120 Yes. In a 24 interview, he stated he owns a marijuana 00:16:07.120 --> 00:16:09.879 dispensary, which is a fascinating shift, if 00:16:09.879 --> 00:16:12.100 you think about it, going from illicit cocaine, 00:16:12.460 --> 00:16:15.539 which ravaged communities, to legal cannabis, 00:16:15.700 --> 00:16:18.419 which is now a heavily regulated tax generating 00:16:18.419 --> 00:16:21.000 industry. It really mirrors the changing legal 00:16:21.000 --> 00:16:23.159 landscape of the whole country. Absolutely. And 00:16:23.159 --> 00:16:25.820 he's an author, too. He co -wrote his autobiography 00:16:25.820 --> 00:16:28.980 with Cathy Scott. It was actually nominated for 00:16:28.980 --> 00:16:31.759 an award, the Forward Review's Indie Fab Best 00:16:31.759 --> 00:16:33.960 Book of the Year in the True Crime category. 00:16:34.500 --> 00:16:36.879 He clearly wants to make sure his version of 00:16:36.879 --> 00:16:39.399 the story is the one people actually remember. 00:16:40.100 --> 00:16:41.860 He's definitely managed to stay in the public 00:16:41.860 --> 00:16:44.980 eye, though not always entirely without trouble. 00:16:45.019 --> 00:16:47.340 There was that incident back in 2015. Right, 00:16:47.399 --> 00:16:49.860 the traffic stop. Police pulled him over and 00:16:49.860 --> 00:16:53.899 found $100 ,000 in cash in his car. Which, given 00:16:53.899 --> 00:16:56.679 his very well -known history, Looks pretty suspicious. 00:16:57.240 --> 00:16:59.679 If I'm a cop and I pull over freeway Rick Ross 00:16:59.679 --> 00:17:01.960 and he has a duffel bag of cash in the trunk. 00:17:02.139 --> 00:17:05.279 It definitely looks bad. But Royce claimed racial 00:17:05.279 --> 00:17:07.700 profiling. He said the money was purely from 00:17:07.700 --> 00:17:10.640 legitimate book sales and speaking fees and that 00:17:10.640 --> 00:17:12.339 he was carrying it because he was going to buy 00:17:12.339 --> 00:17:14.460 a home. And here's the most important thing. 00:17:14.859 --> 00:17:17.420 Ultimately, the charges were completely dropped. 00:17:18.000 --> 00:17:19.819 They couldn't prove it was drug money, which 00:17:19.819 --> 00:17:23.190 suggests his story held up under scrutiny. It 00:17:23.190 --> 00:17:24.910 seems he really is trying to walk the straight 00:17:24.910 --> 00:17:27.930 and narrow path now. And pop culture still loves 00:17:27.930 --> 00:17:30.890 him. If you watch the television show Snowfall, 00:17:31.490 --> 00:17:34.089 the main character Franklin Saint is heavily, 00:17:34.089 --> 00:17:36.890 heavily influenced by Ross's life. Ross actually 00:17:36.890 --> 00:17:38.750 claims he partnered with the show's creator, 00:17:39.130 --> 00:17:42.029 John Singleton, to make a movie way before the 00:17:42.029 --> 00:17:44.789 show was ever created. He says Singleton disappeared 00:17:44.789 --> 00:17:47.559 on him and then suddenly Snowfall came out. It's 00:17:47.559 --> 00:17:49.819 another instance where Ross feels his life story 00:17:49.819 --> 00:17:53.019 was used without his full participation or compensation, 00:17:53.460 --> 00:17:55.839 though Singleton passed away before anyone could 00:17:55.839 --> 00:17:58.450 fully confirm that exact account. It seems like 00:17:58.450 --> 00:18:00.710 a recurring theme for him, his life story being 00:18:00.710 --> 00:18:02.490 a commodity that everyone else wants to sell. 00:18:02.690 --> 00:18:04.769 It really is. But you have to give him credit 00:18:04.769 --> 00:18:07.069 for his sheer resilience. He went from a high 00:18:07.069 --> 00:18:09.690 school dropout who couldn't read to running a 00:18:09.690 --> 00:18:12.029 billion dollar enterprise, albeit a highly illegal 00:18:12.029 --> 00:18:14.690 one, to facing a life sentence in federal prison, 00:18:15.109 --> 00:18:17.349 to walking out a free man running legal businesses. 00:18:17.710 --> 00:18:19.990 It really brings us back to that central irony 00:18:19.990 --> 00:18:22.670 we started with at the top of the show. Here's 00:18:22.670 --> 00:18:24.910 a guy who was denied a tennis scholarship because 00:18:24.910 --> 00:18:27.309 the system completely failed to teach him to 00:18:27.309 --> 00:18:30.809 read. He builds an empire based on complex math 00:18:30.809 --> 00:18:33.970 and logistics, but nearly loses his life to it. 00:18:34.109 --> 00:18:35.930 And the only thing that saves his life in the 00:18:35.930 --> 00:18:38.609 end is finally getting the basic education he 00:18:38.609 --> 00:18:40.230 should have had in the first place. It circles 00:18:40.230 --> 00:18:42.769 back perfectly. Yeah. The literacy that denied 00:18:42.769 --> 00:18:45.890 him his first dream is the exact thing that allowed 00:18:45.890 --> 00:18:48.170 him to have a second life. So let's zoom out 00:18:48.170 --> 00:18:50.309 for a second. What does this all mean for us? 00:18:50.369 --> 00:18:52.849 Why does the story of freeway Rick Ross matter 00:18:52.849 --> 00:18:55.450 to you today other than just being a crazy crime 00:18:55.450 --> 00:18:57.789 thriller? I think it forces us to look deeply 00:18:57.789 --> 00:19:00.130 at the concept of talent versus opportunity. 00:19:00.930 --> 00:19:03.809 Ross clearly had immense natural talent. He had 00:19:03.809 --> 00:19:06.609 organizational skills, strategic vision, and 00:19:06.609 --> 00:19:08.809 the ability to lead a massive workforce. Those 00:19:08.809 --> 00:19:12.250 are Fortune 500 CEO level traits. He understood 00:19:12.250 --> 00:19:14.619 supply and demand instinctively. Absolutely. 00:19:14.859 --> 00:19:16.859 If he had been born in a different zip code, 00:19:17.240 --> 00:19:19.240 or if a teacher had caught that reading disability 00:19:19.240 --> 00:19:21.720 in the second grade, maybe he's running a massive 00:19:21.720 --> 00:19:25.019 logistics company like FedEx or managing a billion 00:19:25.019 --> 00:19:28.160 -dollar hedge fund today. Exactly. We lost a 00:19:28.160 --> 00:19:30.559 potential business leader to the streets. And 00:19:30.559 --> 00:19:32.480 that raises a really provocative question for 00:19:32.480 --> 00:19:35.740 you, the listener, to mull over. If the educational 00:19:35.740 --> 00:19:38.339 system hadn't failed Ross on that high school 00:19:38.339 --> 00:19:41.150 tennis scholarship, Would the crack epidemic 00:19:41.150 --> 00:19:43.869 in L .A. have looked completely different? Or 00:19:43.869 --> 00:19:47.730 was the market force of cheap cocaine so overwhelmingly 00:19:47.730 --> 00:19:50.710 strong that it was simply inevitable, regardless 00:19:50.710 --> 00:19:53.029 of who was running the logistics? Was he the 00:19:53.029 --> 00:19:55.369 grand architect of the disaster or just the guy 00:19:55.369 --> 00:19:57.529 who happened to be standing there when the floodgates 00:19:57.529 --> 00:19:59.450 opened? That is definitely something to chew 00:19:59.450 --> 00:20:02.289 on. It challenges how we look at history. Great 00:20:02.289 --> 00:20:05.849 men or great forces. In this case, it might just 00:20:05.849 --> 00:20:08.380 be a bit of both. Well, thanks for joining us 00:20:08.380 --> 00:20:11.240 on this deep dive into the real Rick Ross. It's 00:20:11.240 --> 00:20:13.019 a story that challenges a lot of assumptions 00:20:13.019 --> 00:20:16.019 about crime, literacy, and redemption. Always 00:20:16.019 --> 00:20:17.740 a pleasure to dig into the details with you. 00:20:17.920 --> 00:20:19.619 We'll catch you on the next one. Stay curious.