The Kentucky Derby Diaries are a collection of stories OWR will be telling up till the Kentucky Derby on May 2nd. Have any good stories? Post them in the comments or send them to us email@example.com.
In 2003 I had started coming to New York often and Saturday nights were always about fun. Most nights would start with a beer or two (into red ales, a weird time for me) and escalate to Captain Morgan and Coke in no time. This particular Saturday in May was the Kentucky Derby. Obviously I had always been aware of the Derby, but I had never bet or prioritized my night around watching the event. That night this changed and it wasn’t for just that night. At the time New York City had OTB joints (Off Track Betting) where you could just walk in and place a bet on a horse. How amazing? No bookies, no shady online accounts, just a simple transaction. I didn’t know much (or anything) about horse racing, but I knew I didn’t want to pick a favorite (what’s the point) and that long shots were usually that for a reason. I went with a horse named Funny Cide (15 to 1 odds) for $10. I won a quick $150! It was so easy. I remember cashing in my ticket and worrying about the $150 in cash I had. Now I know even the homeless don’t get up for less than two hundred, but at the time I thought I might get jacked. I moved to New York City six months later, coincidence?