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'Freeway Boy' Who Brought Crack to Chicago Regrets Damage Done to Hometown

By Mark Konkol | October 28, 2014 5:27am
 A still from the documentary "Freeway: Crack In The System" Inset: "Freeway Boy" Norman Tillman, who made millions selling crack cocaine in Chicago, said he regrets his part in destroying Chicago neighborhoods.
A still from the documentary "Freeway: Crack In The System" Inset: "Freeway Boy" Norman Tillman, who made millions selling crack cocaine in Chicago, said he regrets his part in destroying Chicago neighborhoods.
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Brick City TV

ENGLEWOOD — Norman Tillman lives with regret.

In the late 1980s, the native Chicagoan helped flood his hometown — and a handful of other big cities — with crack cocaine distributed by his best pal, Los Angeles drug kingpin “Freeway” Rick Ross.

The cocaine-trafficking career of Ross is legendary.

The crack trade made him rich, landed him near the center of the Iran-Contra Affair and got him two life sentences, both of which were reduced.

Ross was an important source in late Pulitzer Prize-winning journalist Gary Webb’s controversial series, “Dark Alliance,” which alleged a link between the CIA and the flood of cocaine in L.A. ghettos.

And now, Ross’s story is featured in two movies: the feature film “Kill The Messenger,” starring Jeremy Renner, and a soon-to-be-released documentary that’s already getting a lot of buzz, “Freeway: Crack In The System.”

In the documentary by filmmaker Marc Levin (with whom I worked on the CNN docu-series "Chicagoland"), Tillman plays a supporting role in explaining Ross’s early years as a crack dealer.

Mark Konkol says the respect Tillman commands helps him reach those affected by addiction:

Tillman — who met Ross playing high school tennis in Los Angeles, served in the U.S. Marines and got a scholarship to play the sport at The Citadel — dropped out of college to sell crack. He played a big role in Ross’s cocaine operation but managed to escape the spotlight and prison time by conducting business in Chicago, Atlanta, Boston, New York and lesser cities in Indiana, Nebraska, Oklahoma and Arkansas, among other places.

When Tillman returned to Chicago — the self-proclaimed “son of a hustler” who grew up in Englewood surrounded by players, pimps and drug dealers who frequented neighborhood pool halls and his aunt’s restaurant, “Helen’s Barbecue” — quickly became a crack-selling millionaire.

He quietly lived like royalty at 4950 N. Marine Drive, “surrounded by white folks with great jobs.”

In Chicago, Tillman says he sold 50 kilos of crack a week and collected about $9 million a month from just about every street gang.

The 24-year-old “Freeway Boy,” was fearless and all about business. His drug-dealing associates enlisted the help of Chicago teenagers eager to make big profits from the easy work of selling dope. He bought so many houses for crack-cooking purposes that he couldn’t keep track of all of them.

“Life in Chicago was like velvet,” Tillman said. “I had more money than the pope. I could do anything that I wanted to do.”

But looking back, Tillman, now 55, says he sees his “success” much differently.

His part in spreading cocaine around the city helped destroy the neighborhoods he grew up in, fueled kidnappings and killings, ruined the lives of just about everyone in his family and turned so many “good people” into “crackheads.”

Freeway: Crack in the System
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Brick City TV

“I go through Chicago now — 63rd and Normal, 64th and Parnell — and there’s entire blocks where houses and families used to be,” Tillman said.

“I have memories of the people who lived in those houses. And all those houses and all those people are gone. People literally smoked up everything — first their jobs, then their assets, then their retirement and then their lives — in a cocaine pipe. My whole family is gone. Man, I am real remorseful about that.”

Tillman, once known on the street as “Freeway Shiddy Slim,” says he hasn’t been involved in drug-dealing since the murder of his little brother in 1990.

“I drove from Chicago straight to the funeral home in L.A. without turning off the car once,” Tillman said. “I saw his body, and that’s when I quit selling cocaine.”

All the money he made quickly slipped away in bad business deals, most notably a $2 million investment in a failed film distribution company. And he says he spent millions more paying legal fees for “some of my guys who got busted.”

He moved back to L.A., and in a stroke of luck, met NFL Hall-of-Famer Jim Brown, who recruited Tillman to work for his “Amer-I-Can” foundation, which aims to teach ex-felons conflict resolution and critical life management skills with hope of helping them become productive citizens.

That’s where he met Dr. Carol Adams, then a Chicago Housing Authority director overseeing drug treatment referrals.

“She asked me if I would be interested in being a drug treatment referral counselor and offered me a job with the CHA,” Tillman said. “I went back to Chicago.”

For Tillman, it was a chance to make amends with his hometown.

“I would work with people to get them in drug treatment at places like Harbor Lights, Haymarket and the Salvation Army,” he said. “The beds were paid for. My job was to get people there. I felt like I was doing something really good.”

These days, Tillman runs a tax preparation software company in Los Angeles and is the CEO of “The Freeway Boys Foundation,” which works to help inmates, ex-felons and families negatively affected by addiction, homelessness and unemployment.

“You know, I’m very remorseful about all the communities narcotics destroyed. I don’t want to glorify the lifestyle that I lived. No way. I was a sellout. I chose to drop out of college to sell narcotics. If I would have understood then what I know now at my age, man, that would have never happened,” he said.

“It’s like they say, ‘If you know better you do better.’ So, I give back. My goal is to help produce productive citizens because I know that if you introduce them to new environments and help them find value in themselves that they can have a better life than the one they had before. Man, I’ll never give up on human beings because that’s like giving up on yourself. And I’ll never do that.”

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