How To Bet The 2021 Kentucky Derby: Triple Crown Tips, Picks & Predictions

Adam Kramer offers his tips for How To Bet The 2021 Kentucky Derby, with his pick and prediction strategy for the famous Churchill Downs edition of horse racing’s Triple Crown, which takes place this Saturday, May 1, with post time at 6:57 p.m. ET. Read our 2021 Kentucky Derby Preview Guide for more details around the Fastest Two Minutes In Sports.

The best part about betting the Kentucky Derby is that logic and analysis put forth tends to fade the moment 20 or so horses collide with one another as they leave a cluttered gate. It’s here, from the very jump, that your handicapping is put to the test.

This, of course, is why we love the Kentucky Derby. There is no horse race more enjoyable to bet. There is also no race as random as this one—three-year-old horses at various points in their development trying to peak on that first Saturday in May.

How To Bet The 2021 Kentucky Derby

Before I dive into my picks, here are a few things I tend to look for in this particular race while combing the Daily Racing Form:

Churchill Downs Distance & Horse Stamina

For most three-year-old horses, 1 1/4 miles is a long way to go. Given how difficult this start is with the number of horses included, I tend to really zero in on horses that (a) look poised to want to run longer and (b) run with a more “closing” style — stalking the leaders and charging toward the front late.

2021 Kentucky Derby Horses’ Average Speed

When reading any racing form, Beyer Speed Figures, which help calculate the speed and performance for a given race, can vary wildly. This doesn’t mean the horses with the top Beyer Speed Figures always win, but it does speak to the class and quality of horse. I don’t become a prisoner to speed, but I have to acknowledge it.

2021 Kentucky Derby Horses That Have Improved In Recent Runs

This, to me, is paramount. How is a horse trending at a given time? Given how few races many of these horses have run in their lives, we horse racing bettors have a limited snapshot to judge. And while the previous two races don’t always indicate future success, a horse trending in the right direction is obviously ideal.

Years ago, before I had kids and jobs and a life that got in the way, I followed breeding, jockey-trainer combos, and the nuances of this incredible sport even closer.

These days, I digest both form and film. And yes, I look for value. There’s a balance to be had in searching for value and betting reckless, and I try to find that cozy middle. This race is about securing a score. And search I shall.

With that, here are some observations on the race and official picks below.


2021 Kentucky Derby Horse Post Positions

1. Known Agenda

2. Like The King

3. Brooklyn Strong

4. Keepmeinmind

5. Sainthood

6. O Besos

7. Mandaloun

8. Medina Spirit

9. Hot Rod Charlie

10. Midnight Bourbon

11. Dynamic One

12. Helium

13. Hidden Stash

14. Essential Quality

15. Rock Your World

16. King Fury

17. Highly Motivated

18. Super Stock

19. Soup and Sandwich

20. Bourbonic


2021 Kentucky Derby Bet Tips

1. The 2021 Kentucky Derby horse field doesn’t have a ton of speed.

Given the inexperience of the horses and the sheer number in the field, this is a big deal. When I look at a race, I start by seeing how I think the race will play out. This is good news for Rock Your World (No. 15), which might be able to get a cleaner start out of the gate. I could also see Midnight Bourbon (No. 10), Highly Motivated (No. 17) and Soup and a Sandwich (No. 19) go for the lead. If a horse jumps out and gets a comfy trip, it could go wire to wire.

2. The Kentucky Derby’s No. 1 and No. 20 posts have fascinating options.

In a 20-horse race, being on the rail in the No. 1 spot is normally suboptimal. This stat from ESPN’s Chris Fallica speaks volumes as to how difficult it is to win or even place on the inside. Still, Known Agenda (No. 1) is a really solid horse that could push this.

On the outside, Bourbonic presents fascinating value in the No. 20 spot with morning line odds of 30-1. This horse, while not as seasoned, can really close and come from the back. If there is more speed than expected, he could come flying.

3. The 2021 Kentucky Derby field does not boast a dominant horse.

At least on paper. And at least not right now. Essential Quality (No. 14) is the morning line chalk, although the horse looks beatable. That is not to say the favorite won’t win, but there are more than a handful of horses that look capable.

That should also make for a very competitive race. The Beyer Speed Figures are good but not great. This is a great, difficult betting race.


My 2021 Kentucky Derby Bet Picks 

Part of the fun of betting the Derby is going from the big score. I will bet a horse to win, place and show and bet a trifecta — trying to land the top three horses in hopes of a big payout.

$50 Win/Place/Show ($150 Total) on No. 9 Hot Rod Charlie (Morning Line Odds 8-1)

To me, this horse has a bit of everything. Its Beyer Figures are extremely competitive—especially the 99 posted in its final start at the Louisiana Derby back in March. It has shown improvement since July of last year.

I do find it fascinating that jockey Joel Rosario is choosing to ride the No. 15 Rock Your World over this horse, but it doesn’t sway my opinion.

Flavien Prat, who has Derby experience and success, is more than capable atop Hot Rod Charlie.

I also think Hot Rod Charlie’s running style is conducive for this race. It will stalk the leaders, which seems ideal. This horse, which has run five races at a mile or more, also looks to have gas in the tank to go longer as my best pick to win the 2021 Kentucky Derby.

$1 Trifecta Box with 7 Horses ($210 Total)

This is where I like to have some fun. For the uninformed horse player, I am picking seven horses. Of those seven, I need three to finish first, second and third in the race. Since I am “boxing” them, they can come in any order.

The more horses you box, the bigger the bet. Ultimately, here are the seven I ended up with—a mix of chalk and some value.

No. 8 O Besos (20-1): I think a faster pace and longer race suits this horse well.

No. 9 Hot Rod Charlie (8-1): I picked him to win. Of course, he’s in.

No. 14 Essential Quality (2-1): I don’t love the value, but the horse is clearly solid.

No. 12 Helium (50-1): A bit of a flyer. Inexperienced but undefeated. Could close strong.

No. 15 Rock Your World (5-1): Really good-looking horse with great form.

No. 17 Highly Motivated (10-1): Great Beyers and always in the mix.

No. 18 Super Stock (30-1): The last race was no joke. Improvement off that and he’s got a shot.

Regardless of how you bet, good luck!


After reading Adam’s tips on How To Bet The 2021 Kentucky Derby, use his 2021 Kentucky Derby Bet Tips & Picks at one of our partner sportsbooks. Don’t miss out on The Fastest Two Minutes In Sports, the first leg of the 2021 Triple Crown, on Saturday, May 3, at Churchill Downs!

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