Arbitrage betting

As mentioned earlier, my sports gambling career began with arbitrage. For those of you who are not familiar with the concept, I'll start with an overview.

Here is a quick example:

SPORTSBOOK #1: Team A +107 vs Team B -117
SPORTSBOOK #2: Team A +120 vs Team B -130

The bettor could bet 1170$ to win 1000$ on Team B with sportsbook #1, and bet 986$ to win 1183.20$ on Team A with sportsbook #2. There are two possible outcomes:

Team A wins. Bettor loses 1170$ with sportsbook #1, but wins 1183.20$ with sportsbook #2 (net profit = 13.20$).
Team B wins. Bettor wins 1000$ with sportsbook #1, but loses 986$ with sportsbook #2 (net profit = 14$).

Back in the late 1990s, arbitrage opportunities were PLENTIFUL and PROFITABLE (you could make much more than 14$ per game). I remember precisely my very first online arbitrage bet: my hand holding the mouse was litteraly shaking. I was extremely nervous about making 100$ bets, even though I knew I couldn't lose. I double-checked several times whether I was betting the right amounts, and the right teams. A couple of years later, I was placing 5000$ bets as if I was betting pennies. Stress-free.

I spent days and evenings checking odds from different sports/leagues, some of which I knew nothing about. I started by having an account with only two bookmakers, and ended up with 10 since it multiplied the arbitrage opportunities.

Several great memories from this wild adventure that lasted 3-4 years (as time went by, arbitrage opportunities happened less and less often, making it not worth my time anymore at some point). I'll never forget the December 29th, 2002 game between the Tampa Bay Bucs and the Chicago Bears. Why? Because that turned out to be the most profitable arbitrage bet I ever made.

On this occasion, I won what I used to call a "jackpot", which meant winning both sides of the bet (rather than winning one & losing one). All sportsbooks had Bucs -0.5 on the third quarter, but BetWWTS (which doesn't exist anymore) had Bucs +0.5 with favorable odds as well. I ended up betting Bucs +0.5 with BetWWTS and Bears +0.5 with other books. Remember that we are talking about a bet on the third quarter alone. Needless to say I was praying for a tie on that particular quarter because I would end up winning all bets.

With roughly 6 minutes left in the 3rd quarter neither team had yet scored any points. So far so good, but the Bears were driving at the Bucs 38-yard line. Thankfully they were stopped and they elected to punt the ball. With 2-3 minutes left, the Bucs completed a 21-yard pass to make it to Chicago's 34-yard line. They were getting in field goal range... They moved the ball inside the 25 but thank God the quarter ended scoreless before they scored a field goal in the early 4th quarter. I was screaming and running all over the house: I had just made approximately 6000$ US. Huge money when you are in your early 20s.

I could go on and on with great stories. I might post more stories eventually. My parents and friends thought I was crazy, thinking I could beat online casinos and sending money over to Antigua or Costa Rica. Or they thought even I won, I'd never get my money back. After seeing checks come in the mail regularly, they all changed their minds. They even started to be interested in what I was doing, and asking about the best money-making bets I had made.

To be 100% honest with you, proving them all wrong was a great feeling. It made me feel like I had accomplished something great. I really enjoyed the 2000-2003 period because of that. It became the main focus of my life at that time, and I'll never forget this out-of-the-ordinary experience.