Revisiting the Highs and Lows of Derby Weekend

2 May

By Lucky Kalanges

Sometimes it only takes one big score to make your year, and that was the case for me on Kentucky Oaks day last year.

I went in on a tight budget for Oaks and Derby weekend and struck lightning with the Late Pick 5 on Oaks Day. For Derby weekend, I like to focus on the Late Pick 5, which has a low 15% takeout. It’s hard to hit, especially on Derby day. But if you can hit one of the two, it will make your weekend and, in this case, it made my entire year a profitable one.

Through the wonder of modern technology, I can look back at exactly how I played the Pick 5 ending with the Kentucky Oaks last year. Here’s the three tickets I played for a total of $186 with the winning horses highlighted.

CD R7 $0.50 PK5 1,5,7,8,9,10/4/6,10/3,7,11/3,10,11,13,14 $90.00 
CD R7 $0.50 PK5 7,9/4/2,6,9,10/3,6,7,11/3,10,11,13,14    $80.00 
CD R7 $1.00 PK5 7,9/4/6,10/3,11/10,14 $16.00

All three plays were tied to Chad Brown’s speedy Backyard Heaven, who I singled as the controlling speed in the Alysheba Stakes over betting favorite and 2017 Kentucky Derby winner Always Dreaming. The latter had gone off form and I thought it was a good bet against short odds that he wouldn’t regain it here.

When I caught Will Call at a price in the TwinSpires Turf Sprint at $15.60, and Backyard Heaven romped as I had anticipated as the 2/1 second choice, my biggest ticket was off and running. I caught another break on a front runner when Devine Mischief drew off at 4/1 odds in an optional claimer. That left me with a 3×5 over the next two legs to pay dirt.

Perhaps my biggest break was when Neil Drysdale’s Toinette posted a 5/1 upset over Chad Brown’s 6/5 favorite Rushing Fall over a firm turf course. Many tickets had Rushing Fall singled, so when I moved on to the Oaks with five horses, I was feeling pretty good.

I still had to sweat out this wicked stretch drive with Wonder Gadot on the outside seeking to make my ticket worthless, and a subsequent rider’s claim of foul for interference in the stretch.

When the objection was denied and Monomoy Girl was declared the rightful winner, my Derby bankroll was a cool four large fatter heading into Kentucky Derby day ($4068.40 to be exact).

This game has a way of bringing you down to earth quickly, however, and that was the case on Derby day when I let my stubbornness get in the way of an even bigger score in the Derby Superfecta. This plays out like an ESPN 30-for-30 voice over.

What if I told you, I had Instilled Regard, the longest shot on the board at 85-1 on my Superfecta tickets, but let nearly $20,000 get away because I didn’t use Breeders’ Cup Juvenile winner Good Magic in second or third.

I ended up having a great weekend with my Oaks score, but I let a far greater opportunity slip through my fingers in the Superfecta.

This year, I’ll take the same approach, playing the Pick 5 ending with the Oaks and Derby on each day, and trying once again to catch that elusive Derby Superfecta.

The rain might temper my enthusiasm a bit, but I’ll be back with my impressions of the Oaks day card Friday morning.

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