It’s all a big gamble.

I learned to gamble at an early age.

It started before I started going to school. For whatever reason, I was spending a good deal of time with my grandparents, Ed and Regina, during the daytime hours.

On one of those days, my grandpa pulled out a round bank of casino chips and a deck of cards, and we were off. We sat at the dining room table, with him teaching me the ins and outs of Blackjack at first.

It was truly an educational experience, as I learned how to add long before I ever started kindergarten.

Then we moved on to poker. He called it five-card draw, but who really knows? We had all sorts of wild cards, as the dealer always got to choose.

I was even allowed to wear one of his hats (way too big) and chew on an unlit cigar, all the while sipping 7-up out of little glasses. Oh, the joy of it all.

I’m reminded of this wonderful time with Grandpa because on this date, November 4, 1928, Arnold Rothstein was killed. He was one of New York’s most notorious gamblers. Unfortunately, that gambling led to his demise. He was shot and killed during a poker game at the Park Central Hotel in Manhattan.

Shortly after he was shot, the police found Rothstein bleeding profusely at the hotel’s service entrance. They followed his trail of blood to a back room, a suite, where a group of men were playing cards. Of course, no one at the poker table was talking.

Arnold Rothstein, like me, started gambling at a young age. It appears he had a real talent for playing numbers. By the time he was a teenager, he had built a small fortune gambling in craps and poker games. Now, here is where Arnold and I differed. My grandpa only let us play with poker chips and sometimes pennies. I didn’t know there could be real money in the whole gambling thing.

Anyway, by the time Rothstein was 20, he owned and operated his own casino.

Here’s the thing. Rothstein became a legendary figure in New York. The reason is that he would go on these incredible winning streaks. But most people around him believed he usually won by fixing the events.

The most famous example was in 1919 when the World Series was fixed. Some of the key players on the Chicago White Sox were paid to throw the games, and it was general knowledge that Rothstein was behind it. Of course, Rothstein denied involvement to a grand jury and escaped indictment.

Throughout the 1920s, Rothstein bought a ton of nightclubs, racehorses, and brothels. He had a huge presence in the criminal underworld. And back then, he was among the richest. His fortune grew to an estimated $50 million.

He consistently padded the pockets of police and judges to evade the law.

But, of course, all good things must come to an end. Apparently, in 1928, Rothstein hit an unprecedented losing streak. Which makes you wonder. At a poker game in September, he lost a hefty amount of $320,000. He wouldn’t pay up, either. He said the game had been rigged.

And then? Two months later, his gambling buddy, George McManus, invited Rothstein to play what would be his final poker game.

As he was dying, the police asked Rothstein who had shot him. Rothstein reportedly put his finger to his lips, giving them a “Shhhhh.” He was keeping the gangsters’ code of silence.

McManus was later tried and acquitted of the crime.

I never did much gambling after my early years. As mentioned, I only thought pennies were involved and couldn’t see the point.

But the bottom line when it comes to gambling?
The house always wins. And unless you are the house, you’re SOL.


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I think we consider too much the good luck of the early bird and not enough the bad luck of the early worm.
— Franklin D. Roosevelt

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Luck is believing you’re lucky.
— Tennessee Williams

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I busted a mirror and got seven years bad luck, but my lawyer thinks he can get me five.
— Steven Wright

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