Chicago Gang Leader Tells All - Raw Interview

This true crime podcast episode of 10 Toes Podcast features Scott Anthony, a former branch president of the Simon City Royals, one of the most notorious Chicago street gangs. Scott Anthony committed his first crime at age 9, was arrested over 100 times as a juvenile, and rose to gang leadership at just 14 years old — making him one of the youngest gang leaders to ever hold power inside the Simon City Royals.

In this raw, unfiltered gang documentary–style interview, Scott Anthony breaks down growing up in Chicago gang culture, becoming a career burglar, and eventually robbing drug dealers as a teenager. His criminal career escalated until he was caught with six kilos of cocaine in Georgia, forcing him to go on the run for five years.

Scott explains what life was really like living in Mexico on the run, how he was eventually captured, and what it meant to serve time in federal prison. After his release, Scott leveraged connections he made while on the run and behind bars to discover a new underground hustle — the Cuban cigar trade, launching an unexpected post-prison chapter of his life.

This episode delivers a firsthand account of juvenile crime, gang leadership, drug trafficking, federal indictments, prison life, and redemption, told by someone who lived it from childhood through adulthood.

🔑 KEY TOPICS & TAKEAWAYS

Simon City Royals gang history

Chicago street gangs and juvenile crime

First arrest at age 9 & 100+ juvenile arrests

Becoming a gang branch president at 14

Robbing drug dealers as a teenager

Getting caught with 6 kilos of cocaine

Living on the run in Mexico

Federal prison experience

Life after prison & Cuban cigar hustle

Gang life vs real consequences

🎙️ ABOUT THIS EPISODE

This 10 Toes Podcast episode offers a rare inside look at how gang culture recruits children, how power is earned inside organized street gangs, and how criminal careers evolve into federal cases. Scott Anthony’s story exposes the reality behind gang mythology and the long-term cost of growing up in the streets.If you’re interested in true crime podcasts, gang documentaries, prison stories, federal cases, and real-life redemption, this episode delivers one of the most intense interviews ever featured on 10 Toes Podcast.

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👉 Kyle On Tiktok https://www.tiktok.com/@federalprisontips

👉 Jason on Instagram https://www.instagram.com/8upjay/

👉 Scott On Instagram https://www.instagram.com/scottanthonyog/