Scott Anthony had already lived a life most people wouldn't believe.
He grew up in Chicago street gangs, robbed drug dealers, trafficked cocaine, fled the United States, lived under aliases, and eventually built a new life in Mexico.
Then he discovered another business: Cuban cigars.
While still on federal probation, Scott says he began traveling to Cuba, buying hundreds of boxes of cigars, moving them through Mexico, and smuggling them across the U.S. border. What started with 40 boxes eventually grew into loads of hundreds at a time.
His customers ranged from wealthy businessmen and cigar dealers to some of Chicago's biggest names—including Michael Jordan.
In this episode, Scott breaks down the rise of his Cuban cigar operation, the border seizures, the people who moved the merchandise, his encounters in Cuba, and why he ultimately walked away from the business and put the money into building a legitimate fitness empire in Mexico.
This is the story of a career criminal who eventually decided he'd pushed his luck far enough.
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IG: https://www.instagram.com/scottanthonyog
YouTube: @ScottAnthonyOG
Website: https://www.scottanthonyog.com/
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0:00 Preview & Scott Anthony Intro
7:12 Gangs, Prison Influence & the Criminal World
14:58 Early Scores & Blowing the Money
21:55 Police Brutality & Run-Ins With Law Enforcement
28:12 Going From Petty Crime to Bigger Scores
38:17 Robbing Dealers
45:14 The $300K–$400K Drug Score
49:40 Shootout With the Cops
56:26 What Scott Was Wanted For
58:09 Fleeing to Mexico
1:07:35 Robbing Dealers & His Cop Cousin
1:12:26 Starting a New Life in Guadalajara
1:18:25 Fake Names & Living as a Fugitive
1:26:02 The Federales Find Him in Mexico
1:34:20 The Federal Plea Deal & Eight Years Probation
1:44:35 Back in Chicago & Life After the Case
1:53:59 How the Cuban Cigar Hustle Started
1:59:09 Smuggling Cuban Cigars Across the Border
2:04:49 Buying Cigars in Cuba & Moving Them North
2:10:12 Michael Jordan & Celebrity Cigar Customers
2:17:09 Smuggling Costs, Profit Margins & $500 Boxes
2:24:05 How Big the Cigar Operation Became
2:30:16 Could the Cuban Cigar Hustle Work Today?
2:39:40 Divorce, Scott’s Books & Final Thoughts
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