Some might consider it odd that I could write "memoirs", seeing as I am a good deal younger than many of the grizzled veterans of the gambling industry, including most of the long-time members of MajorWager. Nonetheless, offshore gambling is a relatively recent invention, and I've been lucky enough to have experienced it from its humble beginnings.
Before the internet, betting on sports was very much a neighborhood endeavor. You knew a guy who knew a guy, or you started talking sports at a rundown corner bar and soon enough a guy found you. You got a phone number, called an hour before kickoff for the lines, and then called back with your bets after pulling as much information as you could from the pregame television shows, hoping you didn't miss any major injury news. Half the time no one even answered the phone so you had to leave a message using the lines in the morning paper and hope he didn't call you back at halftime to tell you that your bet was booked at -7 instead of the -6 you thought you had the whole time. And of course you had to talk in code: "20 times on Cowboys and parlay it 10 times to the under" (translation: $110 to win $100 on Dallas, and a $50 parlay on Dallas and under).
The local bookies, of course, raked you over the coals. Lines were always heavily shaded against the hometown teams, although no one really knew how much unless you had a friend in Vegas you could call for updated lines. No pushes on totals; they counted as a loss, and of course no posted total ever included a hook. Parlays paid a measly 7-to-3. But somehow it was all OK since you were getting your action fix and there weren't any other options anyway. But then the offshore sportsbooks started popping their heads up and everything changed.
It started way on the back pages of bottom-shelf sports magazines, ads promising easy gambling over the phone. Back then, the industry was too small for any national advertising campaigns. This was all pre-internet, and sports gamblers are too small a fraction of the population to happen upon each other randomly. So you might know one or two other guys at most that were willing to gamble offshore and the three of you had to pool your collective knowledge and hard-earned cash and give it a shot since your local guy went to jail and you had no other outs.
How to choose which offshore to use or figure out if a given shop is even legitimate? For all you knew, sending money offshore might well be a one-way ticket, regardless of your prognostication prowess. You couldn't exactly call up the Better Business Bureau to get the skinny on your sportsbook of choice. No media coverage, and especially no internet, meant the average punter was pretty much flying blind when choosing an offshore sportsbook, and countless would-be sharps were scammed in this very way.
So you finally suppress that feeling in your gut telling you this is a bad idea, pick one of the offshores with the most expensive looking ad, and give them a call. You notice the ad says they are located in some Caribbean nation, so you are ready for a Hispanic accent. Incredibly, your call is instead answered by a burly-sounding guy with a North Jersey, wanna-be Italian, accent over an incredibly bad phone connection that might be only marginally better than what Alexander Graham Bell had to work with.
Everyone knew it was illegal, but when it came time to send the money, you really started to realize just how shady this whole process was going to be. "How much you sending, a nickel? How about sending a dime and we'll reimburse the transfer fees? OK, head down to Western Union and we'll get you started within a few hours."
Uh...how do I know where one is? Who the hell ever used Western Union before?
An hour later you find yourself in some shady check cashing place with a wad of cash that you know is going to attract unwanted attention when you pull it out. Reaching the counter with a bunch of hundreds in one hand and a crumpled up napkin with the transfer instructions in the other, you know you either look very, very suspicious or like the biggest idiot ever. One of the most uncomfortable moments in the education of any sportsbettor is the first time you get the stare-down from a WU clerk when trying to wire $1000 to Margarita Santiago in Panama---especially when you're ghost white and located in suburban Pennsylvania.
Do you think it's a coincidence that an International Regional Operating Center was opened by Western Union in Costa Rica, of all places, in 1998? Especially interesting considering that Western Union was warned about wiring gambling funds as early as 1995 by the Florida Attorney General and was actually prohibited from doing so in 1997. It doesn't take a genius to figure out that there was some reason behind the sudden influx of gringo cash to small Caribbean nations with lax gambling laws.
Nonetheless, once you got started, it beat dealing with locals, especially if you were in the majority of gamblers who didn't really ever have to worry about collecting a payout. But it still wasn't quite ideal. Sending and receiving money was a pain. You were still at the mercy of the bookmaker to give you a fair line, especially once he figured out that you bet Penn State every week. And there were still those damn international phone connections to deal with. Luckily, the internet was right around the corner and everything was about to undergo a radical change...
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