Confessions of a never convicted Felon

Gambling is not as destructive as war or as boring as pornography. It is not as immoral as business or as suicidal as watching television. And the percentages are better than religion. - Mario Puzo


   I have always held a special place in my heart for sports betting and the people in that market. When you bet a sporting event you are given the illusion of choice (power?) in determining your fate. Then follows a couple hour unscripted drama complete with heroes & goats. When you are on the right side, the high is, well, orgasmic. When you are on the wrong side, well there are always the goats to blame. Sports betting does reside among lifes -EV behaviors. Your losing wagers cost you an extra 10 percent (on straight bets), while your winning wagers are free. So, if 50% of your bets are losers and the other 50% winners, in effect you are giving up 5% to the house with every wager. 5% doesn't sound like much - but give a banker 5% and enough time - and he will own the planet. In theory, the man who can pick 53% winners and 47% losers has the 5% covered. Sounds easy, after all a monkey with a purple crayon should be good for 50%. In reality though, the math is against you and as we all know, math is even less forgiving than, say, Lord Vader.


As an action junkie who wanted to be on the right side of the math, I did the only logical thing I could do.  I became a bookie. I didn't have a lot of clients - maybe it peaked at 30 - but there were some ballers on my client list. 5 figure envelopes were common place.  What fascinated me though, was not the money (which rolled in), - but rather the behavioral betting patterns of my clients.  You had "the chasers".  They would stick a toe in on saturday with a few $100 college football wagers - if they won - they would bet light all weekend - nursing a win so to speak. Its when they lost, the real fireworks started. Sunday Mornings when these people were behind they'd call in a $500 wager or two - trying to get unstuck. By Sunday afternoons, it was a Grand on this team, another grand on the under - $500 parlay or two - and before you know it - they would be stuck 3-4-5 grand.  This was the routine for these people. By Monday night their nuts were in a vice - week in, week out. Some weeks they escaped - other weeks they got buried. Their cousins "the pressers" have the exact opposite problem. They can't stand prosperity. Win a couple of bets for hundred each, and in their mind they are hot and now have a license to bet $500 a game. Win those and they are betting a grand a game. Eventually their hot streak cools, they pick a loser or two - and now they too are stuck. Then there are the habituals. They bet the same way every week. There is value in knowing ahead of time what your client likes.  If I know a guy likes Monday night dogs, why not put the line at 3 instead of 3.5? That half point doesn't usually come in to play - but when it does, its free money. Speaking of half points, and just to show it wasn't all wine and roses as a bookie I present the following:


1997 superbowl Patriots-Packers. When the line was first released the Pack was favored by 14. As the week before the game progressed, bets started to come in on the Patriots, and then more on the Patriots. In fact by Saturday morning (30 hours to kickoff) I had over 22 grand on the Pats catching 14 and a paltry $450 on the Packers. At the time, I had some regulars who I knew wanted the packers - but I was worried they might take their action elsewhere.  So I did what any reasonable businessman would do…… I offered the Packers -13.5.  The packer money piled in - big time.  Parlay this, tease that, yeah two of those , three of that. Before you knew it I had close to 25 grand on the packers.  I had to go back to 14, just to stop the flood. At kickoff, I had 30k on the Pack & $29,500 on the Pats, and I was looking forward to a 3 grand payday - as long as that 1/2 point didn't matter. First half went smooth, Packers up 13.  Patriots put up a quick touch to start the 2nd half - followed by a bolt of lightning. The Pack (Howard) returns the ensuing kickoff for a touchdown and then decide to go for 2, which of course they get. So now they are up 14.  The problem with 14 is I have to pay the Packer betters who laid 13.5, but I can't collect Patriot money which ties at +14. Good news is They have the rest of the third and the whole fourth to get off 14. They had already scored 56 points combined - surely there would be more scoring in a quarter and a half. Uh no. It got so bad, the Packer field goal kicker (Jacke)-who had a pro bowl 30 for 32 regular season - missed a chip shot 33 yd field goal late. The game ended 35-21 &  I lost 30k on that sick 1/2 point beat. 


   When you are a bookie one of the things you strive for, just like in life, is balance. Equal amounts on both sides = risk free payday for the book. When you are a major casino or sportsbook, because of the large number of people betting every game, balance is usually a given. When you are a small outfit, like I was, there were many games where I had big bets on only one side. When I first started out the lack of balance used to bother me. What I came to understand about lopsided situations, is they are fraught with risk - but also opportunity. The wealthiest people on the planet are invariably people on the right side of a lopsided trade. For example, Paul Mcartney is worth zillions because millions of people will pay money for his albums. He is on one side of the trade - the masses are on the other - he gets rich. As a bookie, its the same way. When the masses all bet one way - the game (and wealth) invariably goes the other. The herd always loses. This lesson was valuable as a bookie, but in the investing arena recognizing lopsided trades is priceless. Today I am no longer a bookie, in fact I haven't done it in close to a decade. Online books took many of my clients, the rest I let go. If it weren't for the fact, most prosecutors I know would take everything I have - including my lunch money - without thinking twice - I would probably still book today. It was the easiest money I had ever made in my life.  That is until I discovered the most lopsided trade on the planet, Hello Gold & Silver……..but thats a blog for another day…..