He Made $12K His First Month in the Drug Game—Then Became a High-Stakes Gambler
Freddy Dee grew up in Harlem, Florida, just outside Clewiston, surrounded by stories of street legends in his own family. His grandfather and uncle were known as hustlers and street guys, and Freddy says he grew up hearing stories about robberies, dice games, poker games—even armored trucks. Before long, Freddy began following a similar path. In this episode of Honor Among Thieves Podcast, Freddy Dee tells the story of going from robberies to the Florida drug trade during the 2008 recession. His first opportunity came when he acted as a middleman in cocaine transactions, earning roughly $12,000 in his first month. When his plug realized Freddy already had the clientele, he encouraged him to start buying his own supply. The timing changed everything. Freddy says South Florida was experiencing a serious drug drought in 2008. Supply was limited, cocaine prices were extremely high, and anyone with access to quality product could command premium prices. What started as a middleman opportunity quickly became a lucrative hustle. But the money came with consequences. Freddy breaks down the robbery case that sent him to jail, selling fake product to a customer and believing his arrest was karma, and why he temporarily walked away from dealing. That decision led him into an entirely different underground economy: high-stakes gambling. Freddy describes private Florida card games filled with independent drug dealers carrying huge amounts of cash, poker games where egos could put more than $100,000 on the table, cheating accusations that could turn violent, guns being drawn, and a five-to-six-year stretch where Freddy says it felt like he simply couldn't lose. Eventually, the winning stopped. Freddy talks openly about becoming addicted to gambling, chasing losses, returning to the drug game, and eventually catching another serious case where authorities accused him of trafficking and a judge initially set his bond at $100,000. Through an unexpected series of events, Freddy says he ultimately beat the case—and decided it was finally time to leave the streets behind. This episode covers: • Growing up in Harlem and Clewiston, Florida • Family stories of robberies, hustlers and armored trucks • Freddy's early robberies • Making $12,000 his first month middle manning cocaine • The 2008 recession and Florida drug drought • Cocaine prices, supply and demand in South Florida • Selling fake drugs and the consequences that followed • A North Florida robbery case • Underground Florida poker and dice games • Drug dealers gambling six figures in cash • Guns, cheating and dangerous card-room politics • Freddy's five-year gambling winning streak • Gambling addiction and chasing losses • Returning to the drug trade • The case that resulted in a $100,000 bond • Beating the case and finally leaving the street life Subscribe for real conversations about organized crime, drug trafficking, prison, street culture, gambling, redemption and life after the streets. Chapters 00:00 Freddy Dee: Drug Money, Robberies & $100K Card Games05:03 Family of Street Legends: Robberies, Armored Trucks & Hustlers14:45 Making $12K His First Month in the Cocaine Game20:58 The 2008 Drug Drought: Cocaine Prices Explode in Florida24:12 Selling Fake Drugs and the Robbery Case That Sent Him to Jail34:40 Freddy Dee’s Five-Year Gambling Winning Streak43:18 Inside Florida’s Dangerous Underground Card Games47:36 $100,000 Cash Games With Florida Drug Dealers50:28 The Federal Drug Sweep That Changed Clewiston’s Street Economy56:35 Six-Figure Gambling Wins Turn Into a Losing Streak01:03:14 Returning to the Drug Game After Nearly a Decade01:13:45 Cocaine Trafficking Charge and a $100,000 Bond01:17:24 Beating the Case, Probation Violation & Seven Months in Jail01:22:36 Leaving the Drug Game and Becoming a Civilian 📌 Have an unbelievable story? Apply to be a guest: 👉 https://www.honoramongthievespodcast.com/guest Get Your Merch👇👇👇 https://shop.honoramongthievespodcast.com/products/the-world-is-mine-unisex-t-shirt Become an Honor Among Thieves Patreon Member Join The Underworld👇👇👇 https://www.patreon.com/cw/honoramongthieves?utm_campaign=creatorshare_creator 🔗 Links 📸 Nelson on Instagram https://www.instagram.com/montanatheprophet/ 📸 Freddy on Instagram https://www.instagram.com/freddydee863?igsh=MXcxNXZ2ZWd3dHp0dA== 💎 Sponsors Nord VPN https://bit.ly/honorvpn Learn more about your ad choices. Visit megaphone.fm/adchoices
