It’s Been 30 Years. Why Am I Still A Square?

Note: Squares are gamblers that lose money regularly because they either don’t know what they’re doing or they’re too undisciplined to stick to a plan. Sharps know what they’re doing and stick to the plan. Squares bet for fun. Sharps bet to make money. The vast majority of gamblers are squares.

I’m a square. It pains me to say it but after betting on sports for the past 30 years, I’m still making the same poor decisions, betting the same moneyline parlays on the favorites, allowing the same personal feelings and misguided notions to impact my choices. Why is that? It’s not a lack of education. My parents sent me to a top notch private school in an affluent Chicago neighborhood. I attended a small liberal arts college where we read the great philosophers and discussed the meaning of life. Kant. Socrates. Sartre. Kierkegaard. None of them would’ve taken the Knicks the other night because they believe in Julius Randle’s will to win but for some reason I’m still willing to.

I have no idea how much money I’ve lost since I started gambling but it’s not pretty. In the beginning, in my mid-20’s, I was so excited to learn that you could bet on sports I went overboard. It rivaled the life-changing moment in 6th grade when I realized I could see half of the Playboy Channel’s screen when the line zagged all the way to the corner of our 19″ TV for 3-5 seconds at a time. I watched that channel religiously and locked myself in the bathroom from 1982-1984 coming out only to ride dirt bikes, play fast pitch, eat candy and watch Saturday morning cartoons. Scooby-Doo. Speed Racer. Battle of the Planets. Super Friends and the League of Justice. 1980’s Saturday mornings remain some of the best moments in recorded history.

In the early days, I fell victim to all the classic rookie gambler mistakes. I bet every game because I wanted to have action on every game. I’d take the favorites on the moneyline (to win, not cover the spread) and parlay them with other moneyline favorites because I couldn’t fathom an upset. I’d take the over, never the under, because it’s not fun to root for a lack of scoring in any sport. I’d find a bet that I thought no one knew about, like ‘Will There Be A Run Scored In The First Inning of a Game’ and hone in on it for a few months determined to prove my theory that far more than 50% of the time, a run is not scored in the first inning of most MLB games. Turns out the probability of a run being scored in the first inning of a baseball game is 52.5%. Ugh! I’d chase my losses. I’d chase my losses’ losses. I never bet more than I could afford to lose but when I think of how much money I could’ve made if I’d just invested those gambling dollars in a low cost S&P 500 Index Fund, well, let’s just say the whole enterprise feels like a colossal waste of time.

It all culminated in the mid 90’s when I made a series of bad bets, got in over my head and had to pay a bookie $10k. I had always bet online with overseas companies but during this era the U.S. cracked down on credit card use so I was forced to find a local bookie. I’ll always remember that day. It was sunny outside but blistering cold. Bad things happen when it’s really sunny but deathly cold outside in Chicago.

“Can’t I just write a check?” I remember asking my bookie, who was really just a runner working for a much larger organization.

“These guys don’t take checks,” he said. “When the number gets this big, they want cash.”

Two things to note here. The first is that getting $10k in cash and walking out of a bank is not fun. The teller immediately judges you because they think you’re involved in some kinda international drug ring. The second thing to note is you immediately become paranoid that everyone is watching you even though no one is watching you. I had four envelopes with $2500 in each and it felt like I was carrying the crown jewels or something. The four envelopes were then to be placed in a nondescript brown McDonald’s bag.

“Can it be a Wendy’s bag? Or a Burger King bag?” I asked.

“Just put it in a brown bag and stop being such a smart ass all the time,” the bookie said.

I was told to meet in an alley off Michigan Ave. near where I worked at noon. I remember standing there in the alley, shivering, McDonald’s bag in hand, thinking, ‘How did I get here? Why didn’t I study harder in school? If only I had a law or medical degree, then I wouldn’t be freezing my ass off in a random alley with $10k in a brown McDonald’s bag. I’d be litigating an important case in front of the Supreme Court and being interviewed by Linda Greenhouse or sewing up a ruptured spleen.’

A thousand ideas raced through my head.

‘What kind of car would they drive?’

‘Should I just take my money and run? Run where? Around the block? To Mexico?’

But the thought that rose to the top was ‘Don’t get in the car with them.’ It’s funny, my mom always told me as a kid to never get in the car with strangers but here was the first time that advice was actually coming in handy. I ran through all the things I would say if they asked me to get in the car with them.

‘I’m claustrophobic.’

‘I have to get back to work. I work in advertising and our client needs a new tagline by 2 and often the first hour of taglines you write are really just throw aways.’

A black Mercedes pulled into the alley and came to an abrupt stop. One guy got out of the passenger’s seat. Tall. Black leather jacket. Jeans. Sunglasses. A walking stereotype.

“The god damn Bills,” I said, trying to make friends. You can’t trust the fuckin’ Bills.”

He reached out his hand. I reached out to shake it. He laughed and grabbed the bag with his other hand. He turned, walked away, got back in the Mercedes and they sped past me. The whole transaction took less than 15 seconds.

What a dick.

That day I realized that not only was I a square but that I just paid someone $10k for the privilege. I vowed never to have to go into a Chicago alley on a blistering cold day with $10k in a McDonald’s bag ever again and never to entertain the thought that I could make a living as a gambler. I’m much happier investing my money in the stock market and watching it grow over time then watching it slowly slip away because the Nets couldn’t beat the Wizards at home with Durant and Kyrie both on the floor in the closing seconds and why did it even come down to that in the first place?

The other thing I realized (and I’ll write more about this later) is that whether I bet $20 on a game or $2000, the dopamine rush is the exact same. The thrill, for me, is looking at the games, like the box scores I spent my childhood reading, and trying to predict the outcomes. As a gambler, if you win 52.38% of your bets (if the juice is -110) you break even. Anything above that and you’re profitable. Since I started keeping track of all my bets on The Bad Gambler, my winning percentage is 60%. Pretty sharp. But I’m smart enough to know it’s just for fun and realistically, I’ll always be a square.