Life is a Gamble - Jon Rogers of Carib Sports

Jon Rogers was an old-school bookie. He started booking baseball with his classmates in 6th grade, graduated to parlay cards in high school, and went pro after high school. He lived, and booked through a seismic change in the bookmaking industry. He went from the old days of taking bets over the phone, writing on slips of paper, to moving offshore, and the rise of internet betting. Show Notes [00:00] Introduction of bookmaker Jon Rogers of Carib Sports [00:59] Jon’s childhood and early gambling experiences [03:52] Booking parlays in high school and lottery numbers [08:46] State lotteries broadcast drawings [11:11] Kickbacks and paying for protection [13:06] Super Bowl 1990 FBI raid [16:52] Charges, recordings, taxes, and going to Vegas [21:37] Antigua tax laws, bookmaking on paper, then with software [29:28] 1990 case ends [32:32] Continuing operations in Antigua, accepting credit cards, betting volume, and margins. [35:02] 2003 raid, The Patriot Act [46:42] The SAFE Port Act and closing down [48:44] Life after bookmaking, settling the case, and living happily ever after

You can listen to Life is a Gamble - Jon Rogers of Carib Sports online on Radio and Podcast. Open the player on this page to stream the available audio.

Life is a Gamble - Jon Rogers of Carib Sports is an episode from Gambling With an Edge by Bob Dancer & Richard Munchkin.

This episode is 54:58 long.

This episode was published on Sep 22, 2025.

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