[Jackie Jenkins] and I both really liked the Ben Colebrook horse (Sacred Luna, who went off at 43-1). I was at Mike Maker’s barn that morning and I had asked him what he thought of his horse in that race (Sardinia) and he said, ‘I think he’ll clunk up for third or fourth.’ So we had our strong opinions on the top two and used Mike’s horse and that’s how we backed into the tri for $20 (worth $9,748) and we also had a $50 exacta ($4,235) and $200 on Verve’s Tale to win ($480). If we had gotten 3-1 then I would have bet the whole bankroll on him just to win. I had been chasing that horse for a while and he had terrible rides his last two starts. I told Jackie that the horse was five lengths better than this group as long as Joe Bravo doesn’t fall off.
“In the race where I had to bet half my bankroll – which was $7,500 – we just did the math and figured out how to bet so we just had the takeout. We were in a very good spot – still a few thousand ahead even after betting that $7,500 – and it would have been foolish to do anything else. I was just trying to mitigate losses so we ‘dutched’ the field and bet every horse an amount that would pay us $7,000 to win. A few of the guys around us were nice enough to help with the math.”
So you essentially won the contest off of one race?
“It’s nothing for me to bet a few thousand into a race but I’ve noticed a lot of these guys are very conservative. A lot of them are just hanging out. Even when I’m at the track on a regular day I’m really trying to crank something and make something happen. I may bet only one race all day but I bet it like I mean it. I think we have an advantage that way, especially in live money contests, because a lot of the competition is just playing to keep their bankroll until the end and then make one stab.”
How long have you been a contest player?
“I just got into these contests in the last two months. We’ve picked up more than $20,000 in those high-stakes Derby Wars contests. Jackie had already won a seat to the BCBC and he was the one that said I should try to find some of the contests where there might be a soft spot. We’ve been doing really well.”
I understand you’ve been a serious horseplayer for many years, though, long before you tried contests?
“I’ve filed my taxes for the last 10 years as a professional gambler, all derived from horseracing. I turn a very steady profit with the horses. I met Jackie when I bought some horses for his uncle and we struck up a friendship and have been playing together sporadically for a while.”
You also worked on the backside for many years. How do those contacts and that education help your horseplaying?
“I worked for Mike Maker for about a decade in every capacity. I can tell you with absolute certainty that inside information never gets anyone anywhere. Mike’s a very dear friend but the last thing I want to hear from him is that he’s going to win a race because it never happens that way.
“Through my experience of buying and claiming horses I put a lot of weight on the physicality of horses when I’m looking at them in the paddock. I learned a lot being around Mike and trying to see some of the things that he sees. I feel like I have a huge edge over the majority of people I play against because I have a good idea of what I’m looking at. I bet a lot of money into baby races based on pedigree and have had a lot of success doing that but unfortunately they don’t use a lot of maiden races in these contests because most players don’t like them.”
What was the genesis of your interest in horse racing?
“My mom had always owned horses, I guess for tax write-off purposes more than anything, and I got a bug for it. When I got out of school it just manifested into what it is now, which is a full-time job.”
But you do have a traditional full-time job, correct? As an insurance executive?
“I do have a full-time, nine-to-five kind of job, but I put just as much into my gambling. I had an extreme IRS audit because of all the money I move around and my accountant – he’s the best, he won a big tournament at Churchill Downs this year – he suggested I get a job to offset some of the other stuff we had going on. But we’re all squared away with the IRS now.”