Don’t do as I did

Dice thrown over a stairwell

Don’t gamble away your life

Bragging about betting on Trump: setting a bad example


As you may already know, in 2015 I bet on Donald Trump.

I feel uneasy about my telling the entire world that I did. Of course that’s how I can boast that I understood the Trump phenomenon long before the vast majority of observers.

But I’m also sending a disturbing signal in favor of gambling: placing bets on an event, then imagining yourself enjoying an unexpected, resounding victory.

The thing is, you hear a lot about the rare success stories, not so much about the countless losses.

The House in the end is the only winner. But many people get caught in the trap. Don’t call them suckers. Even brilliant minds get duped. That could be you, if you are not careful.


Most people are not good at math; and even when you rationally understand that your odds of winning are abysmal, you may choose not to act rationally, because either

A. you crave for the emotion associated with winning


B. you have financial problems and you desperately hope that a miracle win could save you

In both cases you are on the path to ruining your life. And the life of people around you.


The more you play the more guaranteed is the result of you losing lots of cash.

But beware of the temptation of getting into games that are instead at least partially based on ability, as I did: here too you may be wasting countless hours in the process of giving away your money to someone who’s smarter than you.


Pretending I could win through superior knowledge. Proudly losing.


Being a soccer football fan I thought that my knowledge of the Italian Serie A league could offset the handicap represented by the cut taken by the betting agency. The idea is that you may predict results better than them, enough to actually win something.

It doesn’t usually work. But you easily run the risk of underestimating your total losses and overestimating your actual abilities.

Many years ago I won a small sum. I have a vivid memory of the circumstances: it was the end of the season; I had bet on a combination of matches, including one involving the Napoli (Naples) team that desperately needed at least a victory (plus a combination of results from other contenders) to avoid relegation in Serie B (the second division).

The 90th minute came. The Napoli match went in overtime and they were stuck in a tie. Due to a combination of other matches’ final results, it was officially over: even scoring and winning wasn’t enough to avoid relegation.

Nonetheless, during the extra time, while the Napoli supporters were already sad and resigned knowing their fate, the player Edmundo aka “O Animal” scored a useless goal. Napoli won, but no one actually cared. Except I was alone in my room, falling to my knees, raising my arms in the air because I won my combination bet. Unbeknownst to anyone else, that inconsequential goal made all the difference, just for me.

It’s a nice story. But the point is that afterwards I gradually lost all the money I won. I became overconfident, easily taking for granted “hunches” that were just illusions. I was predicting results about matches I had no realistic knowledge of. On top of that, most results are unpredictable even to experts.


I was stupid. To be honest, probably my estimate of having ended up even, neither losing nor gaining money, may have been a bit optimistic. Remember we tend to underestimate our losses.

Though my once-in-a-lifetime successful Trump bet absolutely changes everything. But I could jeopardize my record again if I were to get back to sports betting, eventually!


In the long run, even by putting money in games based on your “abilities” and being reasonably good at it, you can hardly expect not to lose. The only winning choice is to stop. If you can stop just after a victory, good for you. But don’t wait for that moment.


The Poker Trap


Another good example involving skill is card games. They say that almost everyone tends to overestimate his/her abilities at poker. Especially suckers being put in a mark position.

A few years ago I spent some time playing Texas Hold’em Poker online. At the time there were lots of freeroll promotional tournaments (you play for free, you may win a small sum or a ticket to participate in a bigger event), so there was no risk involved except becoming addicted to the game. A colossal waste of time, I must tell you; although, not risking my money, I usually played while I was doing something else, like browsing.

Poker in itself is a fascinating game, and it only works when there’s real money at stake. It’s mostly about psychology, once you’ve mastered the math. But most people never bother to understand the odds, and are hopelessly exposing themselves to someone who can read them like a book and patiently take their money away, while they are distracted by the occasional lucky win.


I went to Vegas only once, it was part of a bus tour, and I really don’t feel like getting there again. The place is a monument to all things fake.

I joined a Texas Hold’em table there. Well, guess what… I won.

I won slightly more money than what I gave as a tip to the guide and bus driver. But still. Man, how I’m sending wrong signals in your direction!

This is again a single shot event. I got lucky. If I were to return, I’d quickly get in red territory, then pile on the losses.

I was a little in a hurry, because I didn’t want to inconvenience a travel friend who accompanied me there and was patiently waiting for me to be done with it. This was highly beneficial because people tend to stay at the table for hours, eventually losing. (BTW, Hugh from North London, wherever you are: please contact me! I must have misunderstood your email address! It’s sad to lose a connection with someone you enjoyed spending time with…)

I was a sight to see: the typical novice that needs to be told what he’s supposed to do next, especially handling chips.

At the table I mostly faced a single adversary. A guy who was clearly playing drunk. He was even politely invited by the card dealer to leave the table, after he knocked over his drink all over the green carpet.

The topical moment was when I went all in against Drunk Guy.

I was almost done. I had nothing. Until the very end.

The dealer put the River down, i.e. the 5th and last card of the game to be put on the table. It was exactly one of the only 4 cards in the entire set that I needed to win. Straight (5 sequential cards)!

I initially wasn’t even sure I had won. Everything happened so quickly.

Drunk Guy took the loss, swearing.


Vegas Life


I hope he’s OK now and that day was an absolute exception in his life. But this is exactly the kind of person you become, if you give in to these vices. Drunkenly gambling away your money, while slightly less contemptible people look down on you in embarrassment.

I was lucky, but any expert player could have easily taken advantage of him repeatedly. Mischance has nothing to do with it.

Ultimately, all such games are about the old adage:

a fool and his money are easily parted.


In fact, if you want to understand how someone could make money with gambling besides running a casino, take the 1998 John Dahl movie Rounders.

The character of Joey Knish is, they say, inspired on the life of Joel “Bagels” Rosenberg. A guy who is wasting away his life in poker rooms, but he’s sufficiently boring, disciplined, good at math and -more than anything else- good at reading other people, to barely make a living for his family by targeting weak poker players and taking their money systematically.

See, even winners are miserable in this underworld.


Taking risks, in life, is nothing like the movies. There’s nothing wrong in being good at dealing with risk; in fact, it’s a worthy quality, even required in some important job lines. Here’s the important part: those who are good at dealing with risk are also those who are not enjoying it.

If you like playing with money, don’t.

slot machines, ladies playing

Photo by Alex Cheek (CC-BY-SA-2.0)

I’ll leave you with a couple of scenes, memories that I took from that night in Las Vegas.


One. I really don’t understand the thrill of slot machines. But hey, they’ve got a poison for every taste!

I realized something odd, just by watching the players there, mesmerized by their personal slot machine, sitting there for hours.

Most of them seemed to be women around menopause. This can’t be a coincidence.

I noticed the same phenomenon on other occasions, in bars and tobacconist shops in Italy, wherever you can find a slot machine. Lots of middle-aged-to-elderly women. Could this be a hormonal thing? Some vulnerabilities are not always predictable.

We are designed to survive in a jungle, not to keep cool in some artificial light environment where colorful machines emitting cute sounds promise us huge rewards.


Two. This woman, approximately 25. Pretty, girlish, with long black hair, black stockings and black velvet shorts.

She carried a box of assorted smokers’ articles and accessories around the casino. The box was supported by a strap around her neck. I couldn’t believe my eyes: she seemed to come directly from the 50s, like an extra from some old movie.

She was hailing potential clients, wearily repeating a routine, with the saddest voice. “Cigars!” she cried in a hushed tone. “Cigars!”



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