How to bet the 2021 Kentucky Derby

The Run for the Roses is here. Saturday, we’ll have the 147th Kentucky Derby, and more importantly, this year’s edition will take place on the first Saturday in May. The Derby is always a tricky race to bet, as you not only have very young horses, but you also have a massive 20 horses on the track. That may seem intimidating, but I have something that can potentially help you pinpoint who to place your bets on in the Debry.

Years ago, I came across a forum post from a poster called MoneylineExpress that outlined a 10-step process that whittled down the 20-horse field to just a few viable contenders. Horse racing systems are a dime a dozen and usually don’t work. But to my surprise, this process nailed Animal Kingdom as one of the three horses who could win the 2011 Kentucky Derby. A $2 win bet on Animal Kingdom paid $43.80, so needless to say, the process always stuck out to me. 

Over the years, I’ve used this process to identify my Derby win bets. While the winners haven’t always been longer shots like Animal Kingdom, the process has worked in nine of the last 10 runnings of the roses. The one exception came in 2019 when Country House won as a 65-1 longshot in the slop thanks to the disqualification of Maximum Security. In other words, the process isn’t foolproof, but it’s pretty darn good. So let’s dive into the 10 steps.

(Prepare for the Kentucky Derby with this guide from our friends at OptixEQ!)

First, here’s a look at the field with the trainer and jockey in parenthesis along with their opening line odds:

1 Known Agenda (T. Pletcher/I. Ortiz, Jr.) 6-1
2 Like the King (W. Ward/D. Van Dyke) 50-1
3 Brooklyn Strong (D. Velazquez/U. Rispoli) 50-1
4 Keepmeinmind (R. Diodoro/D. Cohen) 50-1
5 Sainthood (T. Pletcher/C. Lanerie) 50-1
6 O Besos (G. Foley/M. Pedroza) 20-1
7 Mandaloun (B. Cox/F. Geroux) 15-1
8 Medina Spirit (B. Baffert/J. Velazquez) 15-1
9 Hot Rod Charlie (D. O'Neill/F. Prat) 8-1
10 Midnight Bourbon (S. Asmussen/M. Smith) 20-1
11 Dynamic One (T. Pletcher/J. Ortiz) 20-1
12 Helium (M. Casse/J. Leparoux) 50-1
13 Hidden Stash (V. Oliver/R. Bejarano) 50-1
14 Essential Quality (B. Cox/L. Saez) 2-1
15 Rock Your World (J. Sadler/J. Rosario) 5-1
16 King Fury (K. McPeek/B. Hernandez, Jr.) 20-1
17 Highly Motivated (C. Brown/J. Castellano) 10-1
18 Super Stock (S. Asmussen/R. Santana, Jr.) 30-1
19 Soup and Sandwich (M. Casse/T. Gaffalione) 30-1
20 Bourbonic (T. Pletcher/K. Carmouche) 30-1

(Check out Benny Ricciardi's full Derby preview!)

Step 1

Remove all horses who did not run at least 1 1/8 mile in their last prep race. Horses who have not run at least this distance will have a tough time with the 1 1/4-mile distance in the Derby. Every winner for the last 27 years has run at least 1 1/8 mile in their final prep race before the Derby.

Eliminate: 

12 Helium – last race was the Tampa Derby at 1 1/16.
16 King Fury – last race was the Lexington Stakes at 1 1/16.

Step 2

Remove all horses who did not finish at least fourth or better in its final prep race. No horse has won the race with a finish worse than fourth in its last prep race going back to 1962. The 2019 winner Country House finished third in its final prep race before the Derby, but often the winner is coming off a win in its final prep race.

Eliminate: 

3 Brooklyn Strong – Finished 5th in the Wood Memorial.
4 Keepmeinmind – Finished 5th in the Blue Grass Stakes.
7 Mandaloun – Finished 6th in the Louisiana Derby.

Step 3

Remove all horses who did not race at age 2. All of the horses in the Kentucky Derby are three years old. While that may seem quite young, we never seen a horse step onto the track at 3 and compete at this level. 

Eliminate: 

5 Sainthood – First race was Jan. 9, 2021.
15 Rock Your World – First race was Jan. 1, 2021.
19 Soup and Sandwich – First race was Jan. 28, 2021.

Step 4

Remove all horses who were not first or second with a furlong to go in either of their last two starts before the Derby. Sure, Giacomo won the roses from back in sixth with a furlong to go in 2005, but those sorts of comebacks are rare in the Derby. The winner will almost always be up front with a furlong to go.

Eliminate: 

6 O Besos – Was 4th and 5th with a furlong to go in last two races.
18 Super Stock — Was 3rd and 5th with a furlong to go in last two races.
20 Bourbonic — Was 5th and 3rd with a furlong to go in last two races.

The contenders

1 Known Agenda (T. Pletcher/I. Ortiz, Jr.) 6-1
2 Like the King (W. Ward/D. Van Dyke) 50-1
8 Medina Spirit (B. Baffert/J. Velazquez) 15-1
9 Hot Rod Charlie (D. O'Neill/F. Prat) 8-1
10 Midnight Bourbon (S. Asmussen/M. Smith) 20-1
11 Dynamic One (T. Pletcher/J. Ortiz) 20-1
13 Hidden Stash (V. Oliver/R. Bejarano) 50-1
14 Essential Quality (B. Cox/L. Saez) 2-1
17 Highly Motivated (C. Brown/J. Castellano) 10-1

The field is now whittled down to nine horses with the second favorite in Rock Your World taken off the board. From here, we will no longer be eliminating any horses. Instead, we’re going to award a point to the horses for each of criteria box they check. 

Step 5 

Give a point to any horse who won a race of at least one mile at 2 years old.

Point to:

1 Known Agenda, 2 Like the King, 9 Hot Rod Charlie, 10 Midnight Bourbon, 13 Hidden Stash, 14 Essential Quality

Step 6 

Give a point to any horse who ran one of its two fastest Beyer speed figures in its last race.

Point to:

1 Known Agenda, 2 Like the King, 9 Hot Rod Charlie, 10 Midnight Bourbon, 11 Dynamic One, 13 Hidden Stash, 14 Essential Quality, 17 Highly Motivated

Step 7

Give a point to any horse who ran in a graded stakes as a 3-year-old before April.

Point to:

1 Known Agenda, 2 Like the King, 8 Medina Spirit, 9 Hot Rod Charlie, 10 Midnight Bourbon, 13 Hidden Stash, 14 Essential Quality, 17 Highly Motivated

(Prepare for the Kentucky Derby with this guide from our friends at OptixEQ!)

Step 8

Give a point to any horse who won a graded stakes race.

Point to:

1 Known Agenda, 2 Like the King, 8 Medina Spirit, 9 Hot Rod Charlie, 10 Midnight Bourbon, 14 Essential Quality

Step 9

Give a point to any horse who finish in each of its last two races was no worse than its place with one furlong to go in the race.

Point to:

1 Known Agenda, 2 Like the King, 8 Medina Spirit, 13 Hidden Stash, 14 Essential Quality

The results

1 Known Agenda  — 5
2 Like the King  — 5
14 Essential Quality —  5
8 Medina Spirit  — 4
9 Hot Rod Charlie —  4
10 Midnight Bourbon —  4
13 Hidden Stash —  4
17 Highly Motivated —  3
11 Dynamic One — 1

(Learn the basics of betting on the horses with our Horse Betting 101.)

Step 10

Winning horses nearly always have four or five points from the previous five steps. We can toss Highly Motivated and Dynamic One from the pool. In our final step, we’re going to look at the Beyer speed figures for this group. To eliminate any one-hit wonders, we’re going to take the second-highest Beyer figure for each of the seven remaining horses.

14 Essential Quality  — 96
10 Midnight Bourbon —  96
8 Medina Spirit  — 95
9 Hot Rod Charlie  — 94
2 Like the King  — 86
1 Known Agenda  — 82
13 Hidden Stash  — 82

While Beyer numbers are far from a perfect metric, we typically don’t see a horse within five points of the top speed take the roses. So that takes Like the King, Known Agenda and Hidden Stash out of the mix. So we’re left with the following horses as the top contenders:

14 Essential Quality
10 Midnight Bourbon
8 Medina Spirit
9 Hot Rod Charlie

Essential Quality is far and away the favorite for this race with an opening line of 2-1. There’s a chance it gets bet down even further before post, so we aren’t likely to get any value here. While Hot Rod Charlie is the fourth favorite to open at 8-1, he’ll still offer a reasonable price for win bets. Medina Spirit and Midnight Bourbon will almost certainly give us longer odds and offer some very intriguing potential for betting purposes. 

We also should take into account the jockeys for each horse. Luis Saez will be aboard Essential Quality. While Saez hasn’t won a Derby, he was the jockey for the disqualified Maximum Security in 2019. Hot Rod Charlie jockey, Flavian Pratt, ended up benefitting from that disqualification and won aboard Country House. John Velazquez has the mount on Medina Spirit and is one of the most accomplished jockeys in the field. Velazquez has three Derby wins: Animal Kingdom in 2011, Always Dreaming in 2017 and Authentic in 2020. Mike Smith is a triple-crown winner in 2018 with Justify. He also won the Derby in 2005 with Giacomo. Smith has the mount on Midnight Bourbon.

So there you have it. The process has given us four horses. Essential Quality is unlikely to give us a good price, and given the jockeys, Midnight Bourbon and Medina Spirit really stand out. Win bets on both plus a smaller win bet on Hot Rod Charlie make a lot of sense. Here’s how we could approach this race on a small budget and a larger budget:

(Prepare for the Kentucky Derby with this guide from our friends at OptixEQ!)

The bets

$20 budget

$8 win bet on 10, 8
$4 win bet on 9

$100 budget

$20 win and place bet on 10, 8
$10 win and place bet on 9

Now, I should say that the above process works for identifying candidates who can win the race, but it’s not an approach to use for exotics. Sure, we can use 8, 9, 10, 14 as our key horses, but simply boxing them up in exactas and trifectas isn’t an optimal approach. Here, we’ll need to sprinkle in horses who didn’t meet our criteria above because every year we see those horses hit the board. Here are the other horses I’ll be using in exotics:

Exactas – in addition to the key horses, add the following:

7 Mandaloun
11 Dynamic One
15 Rock Your World
17 Highly Motivated

Trifectas – add these horses to the key horses and exacta horses:

1 Known Agenda
4 Keepin Mind
6 O Besos
18 Super Stock

Here are some sample wagers based on the above picks:

$1 exacta: 8, 9, 10, 14/7, 11, 15, 17 ($16 total bet)
$1 exacta box: 8, 9, 10, 14 ($12)
$1 exacta: 8, 9, 10, 14/8, 9, 10, 14, 15, 17 ($16)
$1 trifecta: 9, 10/8, 9, 10, 14, 15, 17/ 7, 8, 9, 10, 11, 14, 15, 17 ($60)
$1 trifecta: 14/8, 9, 10/1, 4, 6, 7, 8, 9, 10, 11, 15, 17, 18 ($30)
$1 trifecta: 14/1, 4, 6, 7, 8, 9, 10, 11, 15, 17, 18 /8, 9, 10 ($30)

(Prepare for the Kentucky Derby with this guide from our friends at OptixEQ!)