When my brother and I were in high school, and still living with our parents, I asked him, “What do you want to be when you grow up?”
Without hesitation, he said, “I want to be a High Roller.”
Well, it makes sense, then, that he would spend the last years of his life living in the gambling town of Biloxi, Mississippi. I had the joy of living with him down there for over a year. He had a suspended license at the time, and I was his chauffeur. One day he asked me if I would take him to the casino. I didn’t really feel like it. Gambling wasn’t my thing. He kept pestering me, though, and finally I made a deal with him: we’d stay for one hour, and we’d split whatever we won. He agreed, and off we went. When we got to the casino, he went to the card tables and I went to the slots. Within just a few minutes I had lost my limit—money which I couldn’t really afford to lose. I decided to spend the remainder of the hour walking the pier overlooking the Gulf, and try to shake this miserable feeling of just having pissed away money for no good reason. When the hour was up I went and got Matt. He sat at the table with this wild look in his eyes. He was on a roll and didn’t want to leave. I was eventually able to convince him, and we started walking out. Apparently, he had won several hundred dollars and was balking at our agreement to split it in half. He reluctantly said, “I’ll give you $100”, which I was more than satisfied with.
After I moved away, Matt continued to live down on the coast by himself. And, a year or so before his death, he won $75,000.00 in a single run at the Blackjack table, and was subsequently banned from that casino.
Right before he died, he described to me what it was like to walk into a bank and deposit $75,000.00. I think, what he was trying to describe, was what it felt like to be a High Roller.