Legend has it he was owed so much money he contemplated staying behind bars after his release date just to collect. Masterana led an early wave of illegal bookmakers who had grown tired of going to jail and had decided to practice their craft in the Dominican Republican and other islands in the Caribbean, where bookmaking was sanctioned and they at least had a legal argument on their side. He was, in fact, one of the more notorious characters in the history of the racket. These days, Masterana and his peers are under renewed heat from federal authorities over their role in offshore betting and the use of the Internet to further their fortunes. Although they have crafted a persuasive legal argument that their activities are legal, the odds are against them prevailing in the long run.
Courts are slow to indict on sports gambling, but they are even slower to acquit.
The island bookmakers have further complicated their business and their reputations by the recent failure of dozens of offices, which sources say began shutting down immediately following the Super Bowl and have stiffed thousands of bettors throughout the nation. They'd better hope none of those irate customers wears judges robes. At 71, with too many felonies to mention, the odds are against him living happily ever after in his Caribbean paradise. When they finally vote Frank Masterana off the island, it will be for good. John L. Smith's column appears Tuesday, Wednesday, Thursday, Friday and Sunday.