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2021 Kentucky Derby Best Bets and Wagering Breakdown

SI Gambling insider Frankie Taddeo handicaps this Saturday’s 147th running of the Kentucky Derby from Churchill Downs, including the latest odds and his best bets.

Frankie Taddeo

The wait is nearly over. Following Tuesday’s post-position draw the “Fastest Two Minutes in Sports” is finally here. The Kentucky Derby, following some key deflections in the past few weeks, is expected to have a full field of 20 entrants.

NBC will televise live coverage of the 147th running of the Kentucky Derby on Saturday.

Over the past few weeks, the race has lost top contenders: Caddo River, Concert Tour, Life Is Good and Greatest Honour. The prestigious race will have undefeated Essential Quality for trainer Brad Cox who has been installed as the morning-line favorite.

The race has drawn a solid field of three-year-olds led by Essential Quality (2/1) who enters as a strong favorite but he will have to navigate a clean stalking trip from the outside after drawing post No. 14 which considerate speed drawn to his inside.

The two biggest losers of the Derby draw were easily Todd Pletcher’s Known Agenda (6/1) drawing the dreaded rail, and Chad Brown’s Highly Motivated (10/1) drawing post No. 17. No horse in the history of the race has ever won breaking from post No. 17. Expectations are Javier Castellano will try and send him hard early out the gate, looking to avoid any potential traffic issues. History also shows that we have to go all the way back to 1986 to find Ferdinand as the last winner from the No. 1 position.

On the flip side, the entrants who benefited the most from the draw were Bob Baffert’s Medina Spirit (15/1) who drew No. 8, Brad Cox’s Mandaloun (15/1) who drew No. 7, and Doug O’Neil’s Hot Rod Charlie (8/1) who drew post No. 9. Medina Spirit and Hot Rod Charlie could very well duel for the opening lead which sets up perfectly for their running styles drawing in these slots.

Kentucky Derby Betting Angles/Trends:

  • Top trainers Bob Baffert, Doug O’Neill, and Todd Pletcher have saddled up the last 11 Kentucky Derby winners. If you want to follow that angle here are your choices this year: Known Agenda, Hot Rod Charlie, Medina Spirit, Dynamic One, Bourbonic, and Sainthood.
  • The post-time favorite has won six of the last eight runnings of the Kentucky Derby and that honor will most likely belong to Essential Quality on Saturday.

PACE MAKES RACE: PREFERED RUNNING STYLES

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The pace of the race took a huge hit when Caddo River was forced to withdraw from the race due to a fever. His departure has opened up the discussion as to who will be able to gain the early lead and become the pacesetter? On paper, following the draw, Hot Rod Charlie, Medina Spirit, and Midnight Bourbon (20/1) appear to be the likeliest contenders to vie for that position. Rock Your World (5/1) and Soup and Sandwich (30/1) will most likely be compromised by their post position from getting the early lead they desire at the opening turn.

The question then becomes can Essential Quality, Rock Your World, and Highly Motivated fire clean and fast enough from their outside posts to accomplish their preferred stalking running styles and not get shuffled too far back behind the early speed?

Who will cross the finish line first? Let’s take a look at the odds and dive deeper into this race.

Kentucky Derby (G1)

Racetrack: Churchill Downs, Louisville, Kentucky

Date: Saturday, May 1, 2021

Purse: $3,000,000

Distance: 1 ¼ mile, Dirt

Race: 12

Post Time: 6:57 p.m. EST / 3:57 PST

TV: NBC

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2021 Kentucky Derby Horses of Note 

Listed by post number, name, and odds:

#8 Medina Spirit (15/1) - With Concert Tour and Life is Good out of the Derby bettors are now left with Medina Spirit as Bob Baffert’s shot at another Kentucky Derby win. Baffert, who has six career wins in the Run for the Roses, has won three of the last five runnings with American Pharaoh in 2015, Justify in 2018, and Authentic last year. On paper, this son of Prontico will likely be gunned to the lead by John Velazquez who will look to be among the top flight from the opening gate. We could be looking at a repeat of last year with a horse who has run first or second in all five career races. Top Choice

#14 Essential Quality (2/1) - This son of Tapit, who won the Breeders’ Cup Juvenile as a two-year-old, enters the race off wins in the Southwest Stakes and Blue Grass Stakes. Brad Cox's strongest chance to earn his first Kentucky Derby win is with an undefeated colt who is 5-for-5 in his career. The news that Mattress Mack will be wagering $2 million on him makes Essential Quality a play against for me on the top spot as I search for value in a field of 20. Underneath, Lack of Value

#15 Rock Your World (5/1) - John Sadler has done a great job with this colt evidenced by his impressive win in the Santa Anita Derby. His victory in that Grade 1 followed up two wins earlier this year at Santa Anita. This son of Candy Ride, will need a clean break but the one thing that we all should take note of is jockey Joel Rosario jumping off Hot Rod Charlie in favor of Rock Your World. That is extremely telling with horses that rate out so closely at the top. Threat

#9 Hot Rod Charlie (8/1) - Trainer Doug O'Neill, who won the Kentucky Derby with I’ll Have Another (2012) and Nyquist (2016), is back in 2021 with Hot Rod Charlie. The son of Oxbow was last seen winning the Louisiana Derby on March 20. Although he shocked many people when he finished second to Essential Quality in the Breeders Cup Juvenile at odds of 94/1, I do not envision him pulling off the upset in the Kentucky Derby. My early lean was he could struggle to hit the board, but after drawing in so favorably he has a strong chance to get a piece. Contender

#10 Midnight Bourbon (20/1) - This son of Tiznow looked great in his win in the Lecomte Stakes and is as consistent as they come hitting the board in all seven of his career races. Trainer Steve Asmussen adds Hall of Fame jockey Mike Smith in the irons for the Kentucky Derby. Smith, as we know, has found the winners circle twice in his career in the Kentucky Derby. This colt seems to always be up to the task and is not a horse that bettors should easily look to toss off any trifecta or superfecta tickets. Value Longshot

#17 Highly Motivated (10/1) - Chad Brown’s entry, by Into Mischief, was last seen losing by ‘a neck’ to undefeated Essential Quality in the Blue Grass Stakes. Highly Motivated peaks my interest as a value play who could hit the board. If jockey Javier Castellano can navigate a bad post position into a comfortable mid-pack stalking spot, Highly Motivated could easily make it six consecutive times successfully hitting the board in his career. Use

#16 King Fury (20/1) - Following all the deflections from those ahead of him in the points leaderboard Ken McPeek finds his colt King Fury drawing into the 2021 Kentucky Derby. The son of Curlin looked impressive in his win in the Lexington Stakes at odds of 18/1 as well as also recording two of his three career victories over the Churchill Downs surface. King Fury is easily my favorite bomb longshot to use on all exotic tickets. Top Moonshot

UPDATE - King Fury has been scratched for the Kentucky Derby

Kentucky Derby Formula Rankings

  • #8 Medina Spirit
  • #14 Essential Quality
  • #15 Rock Your World
  • #9 Hot Rod Charlie
  • #10 Midnight Bourbon
  • #17 Highly Motivated
  • #11 Dynamic One
  • #7 Mandaloun
  • #1 Known Agenda
  • #16 King Fury (Scratched)

CONTENDERS

#8 Medina Spirit

#14 Essential Quality

#15 Rock Your World

#9 Hot Rod Charlie

EXOTIC SLOT POTENTIAL

#17 Highly Motivated

#10 Midnight Bourbon*

#11 Dynamic One**

#1 Known Agenda

#7 Mandaloun

*Top Longshot

**Top Moonshot

BY THE NUMBERS: EQUIBASE TOP SPEED FIGURES

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Kentucky Derby Betting Breakdown

Frankie Taddeo, SI Gambling & Fantasy Analyst / Vegas Insider (@Frankie_Fantasy)

This race will boil down to whether Essential Quality can make it a perfect 6 for 6 at likely short odds? I just can not back him in the top spot at expected short odds in my bigger wagers. 

My top play is #8 Medina Spirit (15/1) who I will use with #14 Essential Quality (2/1) and #15 Rock Your World (5/1). In trifecta and superfecta plays I will be using longshots #11 Dynamic One (20/1) and #10 Midnight Bourbon (20/1) as my top longshots looking to spice up the payouts as well as #9 Hot Rod Charlie (8/1). Due to his rail draw, I will be fading #1 Known Agenda (6/1 - despite being extremely high on him prior to the draw.

TOP Exacta BOX: 8-14-15-9-10-17

COST: $1 wager: $30

TOP Exacta Part-Wheel: 8 /1,7,9,10,11,14,15,17

COST: $1 wager: $8

TOP Trifecta Part-Wheel: 8 with 14,15 with 1,7,8,9,10,11,14,15,17

COST: $1 wager: $14

DEEP Trifecta Part-Wheel: 8 with 1,9,10,11,14,15,17 with 1,7,9,10,11,14,15,17

COST: 50-cent wager: $24.50

TOP Trifecta SPREAD Part-Wheel: 9,14,15 / 8,9,14,15, / 1,7,8,9,10,11,14,15,16,17

COST: $50-cent wager: $31.50

*PRIOR to Draw* Trifecta Part-Wheel: 9,14,17 / 9,14,15,17 / 1,7,8,9,10,11,14,15,17

COST: $50-cent wager: $31.50

WIN BETS: #8 Medina Spirit, #11 Dynamic One & #10 Midnight Bourbon (ONLY at Double-Digit Odds)

*May look to add Hot Rod Charlie or Known Agenda at odds of 10/1 or higher at post*

All wagers display ticket cost. All bettors should adjust wager amounts based upon bankroll.

Destin Heath, Trainer at Winstar Farms, Versailles, KY (@dgheat02)

“I would have said Essential Quality was a lock to win but I haven’t really liked his last few as well as his draw outside so much speed. Mandaloun has really worked great leading up to the Derby and he offers solid value at double-digit odds. 

Of the four from trainer Todd Pletcher, I would give the nod to Sainthood over Known Agenda based on his recent works at Churchill Downs as well as unlucky rail draw. Overall I am intrigued by Doug O’Neill’s Hot Rod Charlie who fires consistently as well as Rock Your World who really loved the dirt his first time over the surface.”

Top Choices: 

#9 Hot Rod Charlie (8/1) 

#15 Rock Your World (5/1)

#10 Midnight Bourbon (20/1)

#7 Mandaloun (15/1)

Good Luck!

Over the course of 2020 and into 2021, our Senior Gambling Analyst and Vegas Insider - Frankie Taddeo - has shared his horse racing handicapping formula which has correctly predicted the following winners at SI Gambling:

Travers Stakes - Exacta (8/1), Trifecta (36/1)

Blue Grass Stakes - Exacta (12/1), Trifecta (60/1), and Superfecta (443/1)

Frizette Stakes - Exacta Cold

Desi Arnaz Stakes - Exacta (31/1)

Ontario Derby - Trifecta (72/1)

Tropical Turf Stakes - Trifecta (37/1) - 2021*

Rebel Stakes - Concert Tour - Winner - 2021*

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Frankie Taddeo
FRANKIE TADDEO

Frankie Taddeo is a successful high-stakes fantasy football player who created the first-ever DFS program offered in a Las Vegas sportsbook. Besides contributing NFL fantasy analysis with a Vegas slant, Frankie primarily performs as Sports Illustrated's Senior Betting Analyst providing his significant experience and resources in the sports betting scene. 

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