Reflections on My Up-and-Down Derby Week Handicapping

From a handicapping and wagering perspective, Kentucky Derby week at Churchill Downs was a mixed bag for me.

If I’m being honest, the week got off on the wrong foot when my confident top choice for the Derby—Omaha Beach­­—scratched from the race with an entrapped epiglottis, which sent me scurrying to regroup and rethink my plays.

Overall, the week was filled with good ideas that weren’t executed well enough to land a truly impressive score. On Kentucky Oaks Day, my top choice, She’s a Julie, was a 5-1 winner of the La Troienne Stakes (G1), a nice start to a Pick 4 that got even better when Cummings won the second leg at 22-1. Strategically, I played the second leg well, hitting the “ALL” button to catch a longshot I wouldn’t have had otherwise. But after surviving a single with World of Trouble in the Twin Spires Turf Sprint (G2), my Pick 4 unfortunately died in the finale when Serengeti Empress upset the Kentucky Oaks at 13-1.

It’s easy to say this in retrospect, but I really should have had Serengeti Empress. I was already spreading deep while leaving heavy favorite Bellafina off my tickets entirely, and Serengeti Empress’ best races were more than good enough to challenge for victory in the Oaks. But I was hesitant to back Serengeti Empress after she bled and was eased in her final prep race. When she drew post 13 in a field seemingly filled with fellow speed horses, I left her off my tickets and missed out on a $2,141.35 Pick 4 payoff. At least the day ended on a good note when top choice Hallawallah won the finale at a bit more than 3-1.

Derby Day was similarly frustrating, starting in the opener when Control Stake—a win bet at 6-1 and one of two horses for me in the Pick 5—failed by a nose to stem off Kowboy Karma in an exciting six-furlong sprint. After sitting out the early stakes races, I jumped back in with the all-stakes Pick 4 and caught the 8-1 winner Digital Age in the American Turf Stakes (G2), but the ticket died when Mr. Money upset the Pat Day Mile (G3) with my top choice Hog Creek Hustle second at 16-1. Ouch!

At least my most confident play of the week, Bricks and Mortar, lived up to expectations with a late-running triumph in the Old Forester Turf Classic (G1). After telling anyone who would listen to bet him hard and single him in multi-race wagers, I was happy and relieved to see him prevail, but the winning payoff ($4.20) was lower than I hoped.

Even still, my win bet on Bricks and Mortar was a nice hit, and I was live in doubles to Maximum Security, Game Winner, and By My Standards in the Kentucky Derby. When Maximum Security gamely re-rallied to win after ducking out on the far turn, I was ready to congratulate myself for regrouping after Omaha Beach’s scratch and uncovering the Derby winner after all.

But then, in a fitting conclusion to my week, Maximum Security was disqualified for interference on the far turn and placed 17th. In the blink of an eye, my winning tickets became losing tickets. As on Oaks Day, I nabbed a winner in the last race when Rotation broke his maiden at 7-2, but that was a small consolation after the disappointment of the Derby.

All told, it was a “win a few, lose a few more” Derby week for me. The good news is, the Preakness Stakes (G1) is just a week away, and from a betting perspective, it strikes me as a much more appealing race than the Derby. I’m looking forward to a handicapping rebound!