Blacklist Me

20/20 when we broke but blind when rich

As a 22 year-old I was upstairs at San Manuel talking to a dealer named Steve. I was playing blackjack.

The three days leading up were the three-best in the history of Trey and I’s gambling careers; during a three-night weekend stretch we won $2,000 apiece, per night, netting us a total of $12,000 ($6,000 apiece). It was more money than I knew what to do with. One day at work I remember getting my wallet out for a $1 bill so I could buy a Coke out of the machine, but all I had was something like $3,000 in large bills. It was the best problem I’ve ever had.

Anyway, even at 22 I was naturally bad with money. With that $6,000 I bought the MacBook Air I’m currently typing on, so that’s something, but the remainder went to groceries and rent, but mostly the casino.

On that fourth day, Trey and I went back to the casino. At home we hatched a plan to use the casino as a business for us; each night we would go to win $100 apiece, thinking it would eventually net us $3,000 per month and $36,000 a year on top of what we were already making at our jobs. After all, we were pretty deep in starter cash. It would be easy!

Fuck, were we seriously that naive? Still, we tried.

In the high-limits Trey put $100 down — cash plays — and won. His $100 was already made. I sat at a $50 blackjack table, and on my first hand was given a blackjack on a $50 hand, giving me $75. We were up $175 trying to make another quarter for an even $100 apiece.

With a dangerous amount of cash in our wallets, in the most nefarious setting in our reality, ultimately we spent the next four hours chasing one $25 chip.

But, of course, it never happened. After I lost the next hand, I, too, lost the next several after, or at least enough to make me buy in a couple more times. Before I knew it I had lost $1,600. By that point Trey went off and attempted to get money back and couldn’t, and went down $2,000. But it’s free money! we kept saying.

I took out $200 from the nearby ATM and ended up at Steve’s table looking to make $3,600 so Trey and I could leave even. As I began winning, Steve and I were talking about gambling in general, like odds and stuff, and as I tipped him the thought came to Trey’s head: How much do dealers make? On the night of Trey and I’s greatest collapse at the casino, the thought of my current career in the casino industry was birthed.

I ended up making $800 with Steve, and took two $500 chips to the high-limits. We had already been at the San Manuel for so long, had seen so many hands, that what was a $100 bet? What was a $300 bet? I was numb to the game, which can be both a good thing when everything is working out and equally terrible when it isn’t going well. (Typically, though, when I’m numb from playing blackjack it’s because I’ve spent the whole night chasing money.)

Fortunately, it was going in my direction. I miraculously went from $1,000 to money back — a $2,800 profit — in what felt like no time. It must have been one of the great sequences of blackjack in my history, even though I don’t recall anything about it other than the actual figures I earned.

Looking back, what are the odds of turning $200 into $3,600? The only thing relatable was my birthday last year when I parlayed my last $25 chip into $1,300 for money back. Yikes.

This was where Trey and I fucked up. Royally. He took back his original money and went to a nearby $100-min table and started playing. And I, well, kept playing. I remember looking over at him, as he did at me, seeing his stack progressively sink. I hit a cold spell and was running out myself. Around the same time, we met up front and walked out with nothing in our pockets.

All of that chasing $25.

Writing about that night still gives me a concentrated rush of mental adrenaline, so I suppose this exercise was worth it. There are reasons why nothing surprises me anymore; I’m incapable of letting the little things get to me. I lost my religion at the blackjack tables gambling with money I shouldn’t have been playing with. And it’s when you need it the most when you get the most surefire hand — a 20 vs. a 6, or an 11 vs. a 6 — that it turns into a dealer 21. Luck favors the prepared man, so if you aren’t prepared to have your heart broken then you shouldn’t be gambling in the first place, whether it’s at the casino or at life.

You see it most clearly when you are broke and unhappy.

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