So Andrea is down in Grand Cayman already, and she has started work. So far it sounds great. She sounds really happy, she’s done some good diving, and the people all sound very friendly. These are exciting times for her, and I can’t wait to get down there and join her!
I am still waiting to move down to the Cayman Islands. My application for a work permit has been submitted, but by Cayman law you are not allowed to be in the country while you have a work permit being heard. So Duffy and I are stuck here in the states, waiting for word that my work permit has been approved.
I grew up in a suburb of Albany, NY, and one of the great things about my area is that I am very close to Saratoga. Summer in Saratoga is great, in large part because of the horse racing. I haven’t been to the track in years, but I’m up here packing and getting ready for my move, and I got a call from my cousin Joe that he and his cousin (and I guess also my even-more-distant cousin) Dennis were going to be in the area and were going to the track, so I joined them for an afternoon of fun.
Those who know me know that I’m a good guy to gamble with. I’m active and fun and optimistic, and I enjoy the fun and excitement of gambling. However, this does not mean that I am good at it. I often make exotic bets seeking a big payoff, and I don’t necessarily follow sound gaming strategy, and as a result, I often lose. When I was in law school my friends and I used to make the hour drive from Philadelphia to Atlantic City on a regular basis, gambling what little money we had because we enjoyed the fun and excitement (and relief from the stress of law school). Back then I didn’t care if I would lose $100 on occasion, because I knew that I’d be making big money soon. Once I graduated and started making big money, I was even less concerned with losing, because I could afford it, and I believed I was paying for the “entertainment value” of gambling. Losing a thousand dollars, even two or three thousand, on a trip to Vegas wasn’t that big of a deal, because I had a fun weekend with my friends and the money was otherwise just sitting around — it’s not like I couldn’t make rent, or had to otherwise deny myself of something I wanted, because of a loss.
Now, six months into unemployment (with massive expenses for this little adventure of ours), my outlook has changed considerably. $100 is now a lot of money for me — it’s how much I will earn for a few days of hard work at my new job (once I finally start it). While I still don’t mind paying $10 for a movie or spending money to go out for drinks, some of my more luxurious expenditures can no longer be justified. I can’t go spend $75 on a massage, just because they are relaxing. And I can’t blow money on gambling, just for the fun of it. Money has now become real to me.
With this in mind, I headed up to Saratoga to meet Joe and Dennis. As I said, I haven’t been to the track in years, and back when I used to go regularly (in my high school days), it’s not like I was a master when it came to playing the ponies. I might win a bet here of there, but in the end I’m like 99% of the people who go to the track — I read who the experts pick in the paper and base my bets on them, and I might make a bet on a horse with a good name. And so I knew it would be a good day for me when I saw that a horse called Steve’s Double was running in the fourth race!!
Of course, Steve’s Double did not win in the fourth. But lucky for me, Pays To Dream won in the third! With a name like that, considering what Andrea and I are doing, I couldn’t pass up the horse. After losing in the first two races, before the start of the third I had gone out to the Paddocks to look at the horses. As I watched them go by, a horse named Teuflesberg caught my eye. It was bigger than the other horses, and it looked feisty, like it was ready to run. I decided to bet an exacta box with Teuflesberg and Pays to Dream, and what do you know — my dreaming paid off! They finished 1-2 (Pays To Dream won the race!), and I won $102.50 on my $2 bet!
For me, this liberated my betting for the rest of the day. When I first arrived at the track I was reluctant to bet too much because I didn’t want to lose more than $30 or $40, but after this win, I could bet what I wanted and still walk away a winner. Not that my betting increased too dramatically — I went from betting $4 on each race to betting $8-12 on each race. But I could now bet freely, knowing that I would not lose a significant amount (or anything at all).
As I said, the fourth race produced another loser because of my reliance on Steve’s Double (lesson learned — never trust anyone named Steve again), but in the fifth, I followed my previous strategy of looking at the horses, and a horse named Can’t Refuse stood out to me. I bet him in a few exactas with the favorites that the newspaper guys picked, and he came in first, followed by the favorite, Kid Doc. Another exacta win, this one for $87.50!
In the sixth race, my cousins and I all bet the same exacta, and our horses finished 2-3. We were foiled by the winner, a horse named Texas Elegance, which we refused to bet because of our dislike of President Bush, and therefore all things Texas. And yet again, politics gets in the way of gambling success, bringing back painful memories of when I lost a fortune betting on Mike Dukakis to win the presidency. I still can’t believe that guy lost!
Redemption was mine in the eighth race, though, when Sensational Humor and War Monger finished 1-2, giving me my third exacta win of the day, another $87.50 return on a $2 bet! Deciding that it was smart to leave on a high note, we left after the eighth race, with my winnings totaling $277.50! After deducting what I bet on the races, I won about $200 on the day! For me, this was a huge gambling success!
And of course, this got me thinking. Why am I going to work at a job that pays me $8.45 an hour (yes, this is what I will be making at my scuba job — a sharp decrease from the $150 or so an hour I made as a lawyer!) when I can win tons of money betting on horses? For a while I wondered whether I had in fact made a bad career decision in choosing to give up my law job to be a scuba diver, when clearly I should have given up my law job to be a gambler. As I drove home from Saratoga I was in a state of anxiety, wondering how I could have made such an obviously bad decision, until finally I remembered something very important. The racing season in Saratoga lasts only six weeks. Scuba Diving happens all year around! So even though I would be virtually guaranteed to win at least $200 a day during the track season (based on my results yesterday, which I think must be an accurate indication of how I would perform every day), I would still need to find a way to make a living during the other 46 weeks of the year. And the best way to do that would be by doing something I love, like, say, scuba diving. And since most dive shops won’t give you six weeks off to bet on horses, I guess it’s a legitimate sacrifice to pass up this easy money, for the sake of doing what I love all the time.
And so began, and quickly ended, my dream of a new side job, betting on horse racing. But at least I know that if money runs tight down the line, I do have this skill to fall back on. And I hear that there’s jai alai in the Cayman Islands, and if I can pick a winning horse just by looking at it, imagine how much easier it will be to pick the winning human, especially since the sport is fixed and I can just ask them who is going to win! Easy money, here I come!