Pro Gambler Exposes World Of High-Stakes Betting, Laundering Drug Money, Working As FBI Informant

What does it really look like to live as a professional high-stakes gambler at the very top of the casino food chain? In this episode, Johnny sits down with RJ “Chip” Ryan — a legendary blackjack whale who spent decades betting millions per hand in casinos from Atlantic City to Las Vegas to Macau. RJ tells the raw, unfiltered story of how he went from a broke gambler driving to Atlantic City with his last $5,000, to carrying $10 million in checks, flying private jets, rubbing shoulders with billionaires and celebrities, and taking casinos for millions of dollars at a time. RJ is also known to many as “Robin Hood of Las Vegas” from the Cocaine Cowboys universe — the man who helped launder cartel money through casinos, later cooperating with the feds and offering a very different version of events than what’s been told on screen. This episode dives deep into: -The real math and psychology behind winning at high-stakes blackjack -How casinos court, reward, and ultimately try to break whales -Blowing millions in a single night — and coming back the next day to win it all back -Private jets, penthouse suites, celebrity parties, and casino politics The emotional toll of gambling, addiction, loyalty, karma, and survival -RJ’s personal reckoning after caring for his mother, losing everything, and betting his life on one final run This is not a glamorized gambling story — it’s a brutally honest look at the highs, lows, wins, losses, and moral gray zones of a life lived on the edge. Stick around until the end and decide for yourself: Was RJ a genius, a degenerate, a hustler — or all three? This Episode Is #Sponsored By The Following: Ridge! Take advantage of Ridge’s Biggest Sale of the Year and GET UP TO 47% Off by going to https://www.Ridge.com/CONNECT #Ridgepod CashApp! Download Cash App Today: https://capl.onelink.me/vFut/1ekoiacn #CashAppPod. Cash App is a financial services platform, not a bank. Banking services provided by Cash App’s bank partner(s). Prepaid debit cards issued by Sutton Bank, Member FDIC. See terms and conditions at https://cash.app/legal/us/en-us/card-agreement. Cash App Green, overdraft coverage, borrow, cash back offers and promotions provided by Cash App, a Block, Inc. brand. Visit http://cash.app/legal/podcast for full disclosures. Betterhelp! This December, start a new tradition, by taking care of you. Our listeners get 10% off at https://betterhelp.com/connect Join The Patreon For Bonus Content! https://www.patreon.com/theconnectshow 00:00 Intro: High Stakes Gambling Stories 01:19 Growing Up in Philly & The Family Hustle 04:44 Early Gambling Influences & Lessons 08:09 Professional Gambling: Setting Goals 13:19 The Turning Point: Mother’s Illness and Debt 16:35 This Episode Is Sponsored By RIDGE 18:25 Building a High Roller Reputation 29:01 Life as a Whale: Jets, Parties & Big Wins 36:46 Vegas High Roller Lifestyle & Big Losses 43:34 A Word From Today's Sponsors 46:15 International Gambling & Casino Barred Stories 01:00:53 Advanced Blackjack Strategy & Discipline 01:12:12 Vigilante Gambler: Involvement With Law Enforcement 01:28:01 The Robin Hood 702 Charity Era 01:37:08 Australia, Owen Hanson & The Money Laundering Allegation 01:58:46 Confrontations, Lawsuits & Truth vs. Documentary 02:12:08 Working with the Feds: Taking Down Criminals 02:31:02 Cartel Connections & Final Reflections 02:38:44 Outro: The High Roller’s Ongoing Journey Learn more about your ad choices. Visit podcastchoices.com/adchoices