So before we get into today’s topic, let me just say that I’m one third of the way through this journaling exercise and today is the first night I’m kinda like “eh, I don’t want to do this.” I’ve thoroughly been enjoying doing a nightly journal/write up though, today was just a long day. But we persevere! Onward to gambling!

It’s kind of funny writing this blog tonight because we just had a big Pick 5 carryover pool at Colonial Downs. One of the highlights for a gambler! In yesterday’s entry I talked a lot about gambling in relation to how my relationship with money developed. Today I want to try and look at my lifelong relationship with gambling itself. The activity and occupation, more than the money.

In my baby book, at age 10 days I think, my mom has an entry written down about my dad laying me on the floor and dealing out my first hand of poker. Apparently he won and I started my career on the losing end. So here are some of my strongest and earliest memories of how my life has been tied to gambling. My mom worked in (and eventually owned) a poker room/casino from the time I was four years old up until she sold the business a few years ago. I’m probably throwing mom under the bus a bit here, but I remember being 8 years old and her finishing up work while me and my sister sat at the chefs counter eating dinner and playing pull tabs. She’d put $5 worth in front of us and we’d play. One time I hit a $100 winner and that’s how I paid for a new Easton C-Core bat (i hit nukes with that bat). When I was around 9 and 10 years old, my dad would take me to Longacres a couple days a week. My mom would give me $20 and I’d give that to my dad and he would make my bets. I was a chalk eating weasel and mostly just bet Gary Boulanger to win. One time though, the Space Needle Handicap of 1991 I think? I hit a $2 exacta Captain Condo over Grandstand Gabe for like $44. I asked my dad for the money and he said “I’ll get it to you next week, don’t tell your mother.” My first lesson to not use an untrustworthy bookie!

As teenagers me and my friends would always bet but just on dumb stuff for minute stakes. As we got into high school and college we played quarter poker games, bowled for money, and real poker out at the Indian Casino on Bainbridge Island. My jobs in the summer during college were always at my mom’s poker room. One summer I did accounting, two summers I did surveillance. One summer I just didn’t work. After college and after dropping out of law school, I worked as a floor man at the poker room. It was my first ‘real job’ out of school and for a young kid it was good money. I even wore a suit! I’d get an envelope of cash each night at like 2am when I left work and I’d be betting that money at Emerald Downs on Calder at 9:25am the next morning.

I’d say my gambling started to really dial up around this time. I went from someone who played maybe $30 to $50 at the track to someone who started to bring $200 each day. By 2005,2006, and 2007, I became someone who brought $700 or $800 to the track each time. My betting shifted from handicapping and really trying to just firing. I was a total action player. It was unsustainable for a lot of reasons and in 2010 I pretty much stopped altogether. I was fortunate I never went into debt with gambling but I also never saved up any money because of it.

In those years since 2010 I’ve gotten to know some really great folks who are professional gamblers. And let me tell you, they do not treat it as gambling. At least like how most people think of gambling. To them it’s all about edge. It’s about getting their money in with an advantage against the house or the odds of the game. It’s not about ego, it’s not about handicapping, it’s not about any of that. It’s about betting with an edge. It’s a business to them. When I saw a race-card with ten races, I saw ten chances to make a bet. They might see 1 or 2. They might see 0. They aren’t looking for action. They’re looking for opportunities to take advantage and make money.

Honestly watching these people and listening and talking to them has made me think about gambling in such a different light than I used to. It’s math and strategy and admiring the path to how they got to their decision as opposed to just giving a “yay” if they won and a “awww” if they lost.

Outside of a short stint in real estate (I sold one house in a year), my entire career since I left Law School has been in the gambling industry. Either poker or horse racing. I enjoy the camaraderie of it, the competition of it, and working around and learning from some extremely smart gamblers. Twenty years of working in gambling and it’s still fascinating to me. And it’s still fun. I pinch myself all the time that I get to work at the track let alone announce races.

I will end with this. There are a lot of phonies in this world. The thought on gambling by many is it’s an easy way to get free money. And many gamblers who have never won and have no chance to ever win still believe they can. That makes it a breeding ground for hustlers, stiffs, lowlifes, and liars. People who want to pray on others because they can. I think when you don’t know any better they aren’t easy to spot. You want to believe they have the answers or can really help. I feel like now I can tell within five minutes of talking to someone if they have a clue or if they’re a phony. And I’m not saying I’m some sharp now or anything. But I guess I’d just say be careful who you trust in this world of gambling and be really careful who you give/loan/front money to.