Last week I told you that I was a bad gambler. But I’m not really sure whether I’m truly bad at gambling, or the threat of loss outweighs my enjoyment of the possibility of winning. If only I could find a game where I knew the odds were in my favor! Well, actually, there is one scenario where, given enough fortitude, money and patience, you WILL win. And it involves Roulette. I like to think that I came up with this on my own, but it’s more likely that I read about it somewhere. It involves betting on black or red, or odd or even; any bet that approaches a 50% win rate. Because 0 and 00 are also in play, the actual win percentage for these bets is 46%; good enough. Select a base bet, say $5 and every time you lose, simply double it and make the same bet. Eventually you will win, pocketing a $5 net win. Watch:

$5 bet; lose

$10 bet; lose

$20 bet; lose

$40 bet; win!  You bet 5+10+20+40 = $75. You keep your $40 win bet and earn $40 more = $80.

$80 – $75 = $5, your base bet. Congratulations.

Now this does work, and I have empirical evidence. In the late 70’s my parents moved from Long Island to a crazy place in the Arizona desert named Lake Havasu City. In order to visit, we would fly into the closest airport, McCarran in Las Vegas, then drive 2.5 hours south to LHC. To make things easier on visitors, my parents bought into a time share at a strange place called The Jockey Club. It was basically a Holiday Inn in the middle of the Strip squeezed between the newly built Bellagio and Monte Carlo hotels. It’s an amazing location and to this day big hotels like Planet Hollywood, Aria and Cosmopolitan have been built all around this strange little blue-neon place. My parents sold their interest as maintenance fees and special assessments grew astronomically, but for a while, it was a great place to relax after your flight, spend a night in Vegas, and then head south.

And on one of these visits, late one night, I walked over to a small casino and employed the strategy outlined above. Being cheap, conservative and relatively poor, my base bet was just $2. Much to my dismay, the roulette dealer immediately recognized my strategy confirming that this was no brainstorm. Bottom line: it was the most boring hour I have ever spent gambling. Except when, after 5 losses in a row, I had to wager $64 to keep to the system. In total in that round, I wagered $126 to win that stinking $2.  In the end, I probably walked away with $20 in winnings. Stupid. But maybe if you start with a high enough base bet, and have the cajones to wager much higher amounts just to net out, it might be worth it. Not for me though.

I decided that maybe my buddy Frank was right. If you are going to bet; bet. Don’t make safe bets that deliver little in reward. Let your money live! Let it breathe! Let it party! And if, after that party, it makes its way back to you, it will bring many, many friends. So I don’t gamble often, but when I do, I now go for it. It’s actually much more fun.

For example, a few years back I returned to Vegas to enjoy the high life at the Wynn Hotel for a Sales awards trip. During the trip, Jean plays a little Blackjack and I roll the dice. Now, the best bets on a Craps table are at the Pass line and it’s associated Odds bet. But that’s a bit boring and playing much poorer bets in the Field, Hard Ways, C & E are so much more fun. That’s what I do this trip and…I still lose money. But I had a good time, occasionally winning the weaker bets.

And one night on the way back from a Cirque de Soleil show with a few friends I stopped at a crowded Roulette table. I reached into my pocket, take out the hundred dollar bill burning a hole in my pocket, and plunk it on Black. The dealer allows the cash to play and sure enough, it comes up Black. I scoop up my $200 and walk off, but not before noticing that all the other players are betting many hundreds, if not thousands, on each bet they make. They were not impressed AT ALL with my sudden victory; they just thought it was cute. We walked away laughing about my luck and amazed at the thought of people in this world who could and would toss away such significant dollars in such a cavalier manner. There certainly is a deep chasm between the haves and have-nots in this country, no?

So to bring all this full circle, I’d like to tell you about one final betting experience and it again involves Roulette, which oddly enough, I do not play often.  A few years ago I flew into O’Hare airport to conduct business in Chicago for the week. I stayed at a hotel near the airport that turned out to be across the street from a new casino.

Gambling has evolved over time in Illinois. In the early 90’s the legislature allowed for riverboat casinos that needed to leave their dock in order for gambling to commence. This was inconvenient and led to scheduling issues, long boarding waiting lines, and short gambling sessions. So, about a decade later, the ‘movement’ clause was repealed, and gambling could proceed non-stop on docked riverboats. Huge complexes were built around these floating casinos. Then in 2011, all pretense was dispensed with, and land-based casinos are now allowed by law. (Illinois needs the money!)

Back to the story, I used Yelp to find a decent place for dinner within walking distance and they are ALL located in the casino across the street. I wander over to one of the most crowded casinos I have ever seen! There were people everywhere, 2 and 3 deep at each table. So the casino responds by lifting the minimum bets on all tables to at least $25; pretty steep as an entry level bet. I find a restaurant, have a quick meal, stop at the bar in the center of the building to watch the second half as the Purdue men’s basketball team bests the Michigan State Spartans in the final minute. Happy for my Purdue graduates (Jean, John and Lauren), I jump off my bar stool and head to the exit. On the way I pass a Roulette table where the minimum bet has been lowered to $15 due to thinning crowds. I decide to plunk my $15 on… what else?… number 27. Now most Roulette players eschew bets on single numbers, (less than 3% chance of winning), preferring to bet on groups of numbers. And on this table, as soon as I put my money on 27, seemingly EVERYONE else made bets on groups of numbers that included 27. Gamblers are a superstitious lot. The dealer spun the ball, and since there were quite a few people playing, I was blocked from the wheel. I didn’t need to see it though as once the unmistakable sound of the bouncing ball stopped, a raucous cheer went up from the table, and hands of strangers were slapping me on the back. Yep, the same number my buddy Frank wanted to play back in Vegas…27.

The dealer paid me last and as I pocketed the $540 in chips she said: “Well, that was impressive”. I said “thanks”, but was thinking; “If you only knew, lady. If you only knew.”

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