As many of you know, I am a bit of a degenerate when it comes to sports betting. I wouldn’t say I’m ‘addicted’ to it per say, I just have this compulsion to do it that I can’t control. I can stop whenever I want as long as that’s never.
Now I realize this isn’t a personality trait that makes me unique in anyway, gambling has been happening since the invention of sports. They go hand in hand. As one of the great philosophers of our time once said, they go together like peas and carrots.
But up until about 5-7 years ago, this was mostly done ‘illegally.’ You either had a connection to a real life bookie, or you dabbled in offshore website. I was the latter. The first time I dipped my toe in the offshore sports betting world was when this website was offering a 100% first bet bonus:
I won my first bet on a Packer Sunday Night game against the Bears in September of 2009*. A $30 bet with my winnings doubled on the win. I always say: The worst thing that ever happened to me was winning that first bet. You win that first bet and you automatically think, ‘huh, I’m pretty good at this! Maybe this is what I should be doing all the time!’ All of a sudden I had visions of myself looking like Ted DiBiase with all of money I was going to win betting on games. Jon, you ignorant slut. You’re lucky you’re cute.
Anyway, as the years went on I started to connect with other guys over sports gambling and eventually met a guy in my neighborhood who hooked me up with a ‘guy.’ The biggest benefit to having a bookie is that when if you win, you know you can get paid. As the great Randy Moss once said, ‘straight cash homey.’ Those offshore accounts you never really knew. I cashed out a few times and ended up getting a check from the Royal Bank of Canada that was just about the size of a novelty check you see on Publisher’s Clearing House. I had many a tense moment with bank tellers trying to figure out if they could cash it, or if they needed to report me to the police.
Which brings me to today’s YUGE news in Wisconsin: Legal sports betting at Oneida starts today! Honestly, pretty cool. Although I will say this type of news is over-hyped a bit for people like me. At some point I’ll make my way up there and spend an NFL Sunday in the sportsbook, but when you have a bookie, any bar/library/restroom/couch becomes a sportsbook. That novelty kind of wears off. BUT, this is likely big news for sports fans who have thought about wagering but haven’t because of, you know, legality.
But for those of us with a ‘guy,’ we’re not leaving him for legal wagering at a casino. The bookie/degenerate relationship is one that cultivates over several years. It’s built on trust. Trust that I can get paid on the rare occasion that I win, and trust that I’m going to keep my pinky finger if I miss a settle up day by a few weeks. You can’t put a price tag on that. Hell, my bookie was my emergency contact for a little while there. If I didn’t place a bet for a few days he would check up on me to make sure I was alright health-wise. If I went missing, he’d probably be the first one to piece it together. That’s a relationship that lasts a lifetime, and probably will.
*Yes I talk about my first gambling win like it was a first born child. No, I don’t see a problem with that.
PS: One of my favorite undercurrents of, ‘The Office,’ is Kevin’s relatability when it comes to gambling.
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