What it Was Like Betting Online in the 90’s

To say that online gambling has come a long way is an understatement. Newbies will never know what it was like to bet in the wild west days of the late 90’s internet. There were no review sites. There were few forums. You either took the advice of your buddy on where to bet or you simply picked a sportsbook and rolled the dice.

The local bookie would do, but he wasn’t always available and you never knew what line he was going to give you. It was very much a “take it or leave it” feeling. There was a desire to have better and/or more options. By 1998 there were several online bookmakers that people were using. You would be talking to your buddy at the bar about betting and he would mention he bet the game offshore. Everyone was starting to get a computer by this time and a simple Yahoo search (Google didn’t launch until late 1998 and nobody heard of it until 1999) would get you a list of offshore sportsbooks.

Like I said, there were no review sites. NONE. I remember a handful of sportsbooks right off the bat: WSEX (pictured, 1997 click to enlarge), Intertops & GameDay. Intertops is the only one of these still around and it is doing very well. GameDay would eventually leave the U.S. market and then shut down completely. WSEX went down in flames and the owner ended up killing himself. News history of WSEX

Anyhoo, the scenario would go something like this: You had this pick that you felt very confidently about. You really wanted to unload on it.. maybe a $1000-$2000 (equal to $2,000-$4,000 in today’s money). You call your bookie and his line is 1.5 points higher than what you are seeing online. Or, he has a $500 limit on the game. Your options would be A) to look for another bookie. B) Fly to Vegas. C) Bet offshore. But there were drawbacks to each option:

A) Most bookies in an area know each other and communicate. Some are even working for the same guy. So there was a chance you would be getting the same line. There was also a chance you would piss off your current guy. And finally, you didn’t want to keep exposing yourself and your name to potentially shady underworld characters.

B) Flying to Vegas and getting a room can get expensive. Even in the 90’s you could pay $500 round trip and another $250 for a few nights stay. Even if you won, your win total was compromised by your expenses. Totally impractical. Not a viable option.

C) Unproven and unregulated offshore sportsbooks could take your money and run. How did you know if there was anything more to this sportsbook than a guy with a computer and a website? The best idea was to start small and test the sportsbook. This way you would be prepared for the next time you wanted to bet large.

After you tested the sportsbook a few times and asked for a couple small payouts you could then start trusting it with larger amounts. Payouts back then were strictly Western Union if I recall. There was a bank-wire option too but that seemed too risky for many people.  The legalities were a grey area and there was really no precedent of what would happen if you received a bank wire from an offshore sportsbook. Would some type of flag be raised? Would some guys in cheap suits and government cars show up at your house asking questions?

I can tell you that when you requested your four figure payout from a nameless, faceless person with a mediocre (at best) looking website somewhere in the Caribbean that all types of doubts crept into your mind. When the cashier at WU actually hands you the cash and you walk out it is more of a feeling of relief than joy (are the two inseparable?)

Many sportsbooks have come and gone in the meantime. Many payment methods have also come and gone. When Paypal first started, they were helping fund sportsbook accounts and they made millions doing so (still do overseas). Also, Google made millions of dollars with paid advertisements sending visitors to these sites which were paying as much as $25 per click! So anytime you think of Elon Musk, SpaceX, Tesla, Android, or anything Google, just remember they got their start with money from online gambling. They may minimize it now but it was definitely a huge part of their success back then.

Thankfully now there are sportsbook review websites. There are also much easier and faster payment methods. Sportsbooks have become much more transparent and there is real confidence in offshore betting. America is starting to catch up to the rest of the world and sports betting is available in many states. Soon you will be able to choose from local or offshore sports betting options from anywhere in the country.