Offshore internet bookmaking (NYTimes mag)
Most of the bookmaking companies, though, are a good deal smaller and harder to see, tucked away in strip malls and shadowy side streets. The American proprietors are generally in their 30's and 40's, and for them, the Internet provides not only the means to escape the reach of American law, but also a chance to turn what had been the equivalent back home of small, local shops -- sustained by personalized attention and all the headaches that involves -- into booming, virtual superstores that can rake in action from all over the world. The experiences of these men in Costa Rica, as well as of those elsewhere in Central America and the Caribbean, started out as thrilling adventures in what seemed to them like Las Vegas in the 1950's. But as betting operations multiplied, the offshore business has become hotly competitive and complicated. Worse, in recent years lawmakers and ambitious prosecutors back in the States have been mounting ever more serious legal challenges. Returning home to a normal life now means facing the possibility of going to prison. And so, many of the bookmakers who started out so optimistically are finding themselves locked into an isolated way of life that with each passing day seems a worse bet.