I love the Friday before the Kentucky Derby because of the opportunity to bet one of the more intriguing plays on the gambling smorgasboard. Woodbine is offering a daily double bet spanning the Kentucky Oaks, which is a mile and an eighth for fillies today and tomorrow’s 20 horse Derby at a mile and a quarter. I won’t bore you here with why the double is my favourite bet; just accept the fact that it offers tremendous value against risk and that’s what you’re always looking for in a bet.
The Oaks-derby Double is special though, because it’s really not a daily double, but a bet placed over two days. If you get the winner of the Oaks, you have 24 anxious, exciting suspense-filled, nail-biting, heart-pounding hours to find out if you’ve won the bet. Being alive in the double for an entire day is a delicious experience. You wake up Saturday morning, feeling alive, because you’re sitting on a ticket with half the work already done.
My best friend Jim McKenny, as enthusiastic a horse player as you will find, had an amazing experience in 2006. Knowing I was going to Woodbine to bet the two day double, McKenny phoned me and asked whom I liked in the Oaks. I gave him several numbers – I think they were 5,7, 11 and 13. Much later that day, McKenny called me just as the horses were entering the gate. He was at work, I was watching on HPI. “Remind me of the numbers you gave me,” he asked and I repeated them I heard a popular four letter curse word at the other end of the line.
“I took the 14 horse instead of the 13,” moaned McKenny.
The 14 horse was Lemons Forever, a 42-1 shot. Lemons Forever won and paid $96 and McKenny was live on four horses for the next day. When Barbaro won the Derby ( anyone recall that he was 6-1?), McKenny’s double paid over $800.
OK, so let’s get to my selections today. Rachel Alexandra will be the heavy favourite. She’s won her last four and in doing so, paid $8.20, $2.80, $2.60 and $2.10. I throw out horses like that, because I don’t want such a small slice of the pie. So in today’s Oaks, I will bet #5 Justwhistledixie, #8 Flying Spur and to a lessor amount, # 4 Gabby’s Golden Girl. In the Derby, I like #15 Dunkirk, #10 Regal Ransom, # 11 Chocolate Candy and #6 Friesen Fire. I will bet $4 doubles on 5 & 8 with 6,10,11 & 15 – that will cost me $32 and I will throw in $2 doubles on 4 with 6,10,11 &15 for another $8. $40 well-spent, especially if the 1-2 favourite gets beat in the Oaks today.
By the way, Regal Ransom may be one of those horses who wins the Derby, pays over $40 and you look at him and say…how did I miss that? How could a horse that had won the most money in the entire field go off at 20-1? How could a horse with the fastest 7 -furlong race in the field be such a longshot. Trust me, if Regal Ransom wins, I’ll have some money on it and will boast endlessly in this exact place on Monday!

