Video from the mid-’90s shows tennis prodigy turned cocaine dealer and eventual cog in the CIA-Contra-Crack conspiracy “Freeway” Ricky Ross bounding around his South Central Los Angeles neighborhood. He’s in a striped T-shirt—nothing flashy—shaking hands, dapping associates, and sucking up a whole lot of love for both his superheroic drug dealing skills and putting a whole bunch of his blow money back into his neighborhood by way of new basketball hoops and local businesses.

In March 1995, not long after the video was shot, Ross was arrested trying to buy 100 kilograms from his connect, a Nicaraguan anti-communist named Oscar Danilo Blandón, who had been cooperating with the DEA. Ross did 12 years in prison, and became the most fascinating character in the Iran-Contra scandal, wherein Ronald Reagan’s administration, aided by Oliver North, funded oppositional troops in communist Nicaragua by any means necessary, including dealing arms to Iran and giving the profits to the contras and tacitly—if we’re being generous—allowing cocaine traffickers to move drugs into the United States so they could funnel money back to the Nicaraguan counter-revolutionaries.

As described by journalist Gary Webb in Dark Alliance: The CIA, the Contras, and the Crack Explosion, this was a perfect storm of government complicity, drug war cruelty, and dope dealer ingenuity. As outrageous amounts of cocaine entered the country, guys like Ross bought and sold it, and the boys below him cooked it up and sold it as crack, creating an epidemic in neighborhoods that cops couldn’t give a shit about—at least until they could arrest everybody for the drugs the government allowed into the country with a wink and a nod.

Oliver North’s conviction in the Iran-Contra scandal was overturned in 1991 (six other Iran-Contra defendants were additionally pardoned by George Bush) and he went onto run for Senate and become a popular right-wing talking head. Earlier this month, North was announced as the new head of the National Rifle Association.

“The NRA is pretty ruthless,” Ross said over the phone last week. “With all the gun violence we have in the schools, they’ve taken a pretty hard stance on keeping guns as accessible as they can get it, so them picking Oliver North is not surprising, not surprising at all.”

Guys like Ollie North just win. Ross has seen it before. It’s what happens. These days, Ross is focused on a steady diet of hustles, charity endeavors, and entrepreneurial opportunities—so not all that different from what he was doing in the ’80s and early-’90s, just “legal,” as he puts it.

“I’m selling cars, I’m flipping houses, I’m teaching people how to be millionaires through speaking, I’m mentoring kids, I’m trying to enter the legal cannabis industry,” Ross says. “I’m all over the place.”

In October 2015, Ross was arrested in Sonoma County, ground zero for legal weed in California, for having $100,000 on him and, according to the arresting officer, smelling of cannabis as his car cruised by a cop on the highway.

“They caught me going up the mountain where all the weed is grown at,” Ross says. His arrest was another case of “driving while black,” he says, stressing that only cash was found on him, and that it was part of plans to buy a pot farm. “I was interested in buying into it and still plan on doing that.”

When I first spoke to Ross back in 2012, he was suing the correctional officer-turned-rapper William Roberts (stage name: Rick Ross) for using his government name for profit (a case Ricky lost) and deeply caught up in contemplating his past—all the money he had made, all the lives he had ruined, and how naive he had been.

“I saw a system that was oppressing me and my friends. Not giving us opportunity,” Ross told me at the time. “I thought that cocaine was just another one of those things that whites didn’t want us to have, as blacks. Just like they didn’t want us to live in Beverly Hills and have a tennis court in our backyard. I thought that it was the same thing with cocaine.”

While he now says he was wrong about that, his interest in weed comes from a similar place—where rebellion, racial justice, and capitalism collide.

“Seeing the lack of black participation in the cannabis industry made me want to get it,” Ross says. “The grand schemes I had when I was a drug dealer might be suitable for the cannabis industry. Cannabis and cocaine are side by side—and both were illegal at the same time.”

Ross, the fall guy in a massive scandal that many don’t believe really happened, has become an accessible O.G. and a social commentator, a cult figure. So it was refreshing when one of the country’s most high profile young activists called attention to Reagan, North, and the entire right wing’s dark alliance.

In response to a Fox News interview in which North blamed school shootings on media violence and Ritalin, Marjory Stoneman Douglas High School student turned gun control advocate David Hogg tweeted, “You know what else is a stimulant? The Cocaine that Oliver North helped bring into the US via his criminal support of the Contras in the 80s.”

A follow-up tweet from Hogg declared, “Just think about that: the President of the NRA is a man that Illegally gave guns to terrorists. Like, think about that: someone at the NRA legit had to say you know who would make a great president? This Gun Running felon from the 80s.”

History repeats itself, the past isn’t dead, it’s not even the past and all of that. What that means for guys like Ross is more hustling, more by any means necessary attempts at parity. And for the amoral heels embraced by the Trump administration, given gigs or just a tiny Trump thumbs up from afar, it means more success, more falling upwards. In the past month, we’ve seen tacit torture supporter Gina Haspel appointed to run the CIA, law-and-order nutjob Rudy Giuliani representing the president and bad mouthing the FBI, and now North, running the NRA.

More and more monsters of the 2000s, ’90s and ’80s, returned.

“When we had a run at the Senate that was kinda surprising, then Fox hired him and that was kinda surprising, now the NRA—so nothing surprises me about Oliver anymore,” Ross said. “Nothing surprises me.”