In 1997 the only three books in Oficentro La Sabana were Tradewinds, Caribi (CRIS), and Pelican (Jazz). In those years, the guy who was the biggest surprise and made the most money was the owner of Global Sports. He sold the book and made a ton of cash but he was the first to truly recognize the Internet. He actually had a bank account in Costa Rica closed because he was making too many deposits. Those were also the years when Monti was shooting at the US embassy.
The first offshore sportsbooks I remember were ESB (Jamaica and Pennsylvania), Intertops (Austria), Socco (any island that would take him), Frankie Mastreano, and the team of George and Roger. The last duo were the roots of Heritage, Horizon, Tradewinds, Pinnacle, and I have heard that Lenny (Cascade) may have worked there for awhile many years ago.
Good Luck to you all