Analyzing the Derby and Oaks Pick 5 wagers

Kentucky Derby weekend is a great time to open up the wallet and take a swing or two in hopes of receiving a windfall payoff on a wager. And the Pick 5 might be the perfect play.

The 2019 Pick 5 on Derby Day returned a whopping $72,317.60 for a $2 base bet. On Kentucky Oaks Day, the mutuel after Serengeti Empress took the feature was worth a very healthy $13,826.40.

Here are some thoughts on the Pick 5 for both Friday and Saturday:

Oaks Day

Races 8-12 will comprise the late Pick 5 on Friday, concluding with the Kentucky Oaks (G1). The closing race looks to be logical with three formidable runners, and the rest of the sequence could be chalky, but I think there is a chance to knock off a few of the favorites in the affairs preceding the Friday headliner.

Leg 1 is the Eight Belles (G2) that has two short-priced horses on the morning line, and each looks pretty tough. Getting out of the opening race of the sequence with #1 Mundaye Call (6-5) and #7 Four Graces (7-5) seems fairly logical.

As much as I admire champion #3 Sharing (6-5) and see her as a formidable favorite in the Edgwood (G2), toppling her would add tremendous value to the wager as she will be a single on many tickets. She looks nearly untouchable on paper, but the classy Speightstown filly could be a bit short in her first outing since her Royal Ascot venture. 

Race 10 is the Alysheba (G2) that also has a pair of short-priced horses in #6 By My Standards (7-5) and #2 McKinzie (8-5). But I don’t see it as a two-horse race at all. #3 Owendale (6-1) is my lukewarm top pick in the Alysheba, although others merit consideration as well.

#8 Monomoy Girl (4-5) is another favorite that will be heavily used as a single in the Pick 5, but she will knock heads with two other Grade 1 winners, as well as a filly coming off a lifetime-best performance. I love the morning line choice, and I think she wins with her best performance, but upending her will go a long way in securing a big price in the multi-race play.

The Kentucky Oaks (G1) boasts a trio of sensational fillies in #1 Swiss Skydiver (8-5), #4 Speech (5-1), and #5 Gamine (1-1). As much as I like #3 Donna Veloce (15-1), she would still be a minor surprise to defeat the trio of other Grade 1 vixens, but she's worth tossing in if you can afford it.

Derby Day

The action on Saturday kicks off in Race 10 with the Iroquois (G3), where #10 Therideofalifetime (7-5) is the one to beat. While he is my top pick, I have a hard time making him a single in a race featuring numerous other lightly-raced contenders with room for substantial improvement. Spreading some makes sense to me.

The Distaff Turf Mile (G2) is the second leg and it looks to be all about #4 Newspaperofrecord (4-5). Sensational filly will be even more formidable if there is moisture in the ground. I have a hard time trying to find a filly or mare who will beat her.

I see five solid contenders in the Derby City Distaff (G1) in Race 12, with #4 Bell’s The One (10-1) being the value contender along with the four Grade 1 heroines. She will help boost the wager if she runs them down late.

The Old Forester Bourbon Turf Classic (G1) could easily be an "all" with a very well-matched cast going postward. However, if the course comes up soft or yielding, I will strongly consider singling #8 Sacred Life (6-1). He will be a win bet for me, in any case.

The finale, the Kentucky Derby (G1), could boil down to the two favored runners—#17 Tiz the Law (3-5) and #16 Honor A. P. (5-1).  I would feel good getting to the final leg with the two standout sophomores.

Good Luck!