Kentucky Derby day wagering playbook

Kentucky Derby day wagering playbook
Photo: Sue Kawczynski / Eclipse Sportswire

The Kentucky Derby is a lot of things, and for this player one of my favorite attributes is as a gambler’s paradise.

14 races, full fields, a 20-horse feature…there are legitimate moneymaking opportunities today, and I plan to attack the card by trying to make the most of what I have deemed my best “value” opinions.

In race 8, the Derby City Distaff (G1), I am betting that trainer Neil Pessin has trained Bell’s the One to the nanosecond for this following her seasonal debut in April at Keeneland.

In race 11, the Old Forester Bourbon Turf Classic, my thought is if I liked Bizzee Channel enough to pick in the Mr. D. (G1) (formerly the Arlington Million) then why not here? 

In race 12, the Kentucky Derby, my appreciation for Tiz the Bomb is known by now. I like Pioneer of Medina as well so really wouldn’t mind seeing 9 or 11 run well at big prices. Of course a Bizzee Channel-Tiz the Bomb/Pioneer of Medina double would also be pretty sweet!

As for horses to lean on, I see No. 5 Jack Christopher in race 7 and No. 3 Jackie’s Warrior in race 10 as the most likely winners on the card. I can’t do as much with Jack Christopher, but I don’t mind leaning on Jackie’s Warrior because of my thoughts on higher prices in races 11-12 plus a value play in race 8.

For those who want to play along from home, my “base” ticket in the all-stakes Pick 5 that ends in the Kentucky Derby is 6, 7 with 1, 3, 4, 5, 6, 8, 9, 11 with 3 with 2, 5 with 9, 11. That’s $32 for 50 cents. I’ll key around legs 4 and 5 with the thought if even one of those wins (along with being against the favorites in legs 1 and 2) I’ll separate from the pack enough.

Also worth noting there is a special $3 all-three-year-old Pick 3 that involves the Pat Day Mile (race 7), the American Turf (race 9), and the Kentucky Derby (race 12). I am leaning on the aforementioned Jack Christopher and tossing the favorites in at least one of the other two legs.

For more on that wager, check out mine and Sara Elbadwi's video below.

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