I used to be fairly heavily ($2000 or so per week, around $200-$300/game). I had good years and bad years. In the long haul though I won a bit. What I found was that gambling took away from my enjoyment of the game and since I'm making very good money now, I don't really need the extra income. I quit earlier this football season with no regrets since I started bad and never really caught up. I used an offshore betting service that I have used for the last 5 years (SBC global). I had as much as $15,000 with them at any one time, and they never failed to pay me back the next day (with no fees).
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