Kentucky Derby 2021 – Unmasking a Few Tips for the First Saturday in May

Whether you Win or Lose, the Run for the Roses is back to its rightful spot on the calendar

Betting tips and picks for Kentucky Derby 147

They’re off!! Thankfully on the first Saturday in May this year for the 147th running of the Kentucky Derby.  Although we will still not yet see the traditional crowd of 160,000 mint julep swigging crazies surround Churchill Downs, it will seem more Derby-like this year with Spring just beginning in Louisville. 

And as welcome as "The most exciting two minutes in sports" is it also offers the annual headache for handicappers to select a winner for a variety of challenging reasons.  That being said, here are a few key Kentucky Derby betting tips to keep in mind:

#1 - Lack of Maturity

147th Kentucky DerbyThe top reason for not cashing a winner in this giant 20 horse field is often the most overlooked. In May, these 3-year-olds have not reached full physical maturity as yet. Some simply are further ahead of their peers.  That is why so many very forgettable colts have won the Derby in the past and have gone on into obscure trivia conversation.

It is remarkable how much these colts benefit by extra races and growing just from the period of May into the Fall.  It's the reason why the Breeders' Cup races, run in the first week of November, offer a much truer picture of the best 3-year-olds and a better prediction of who will be stars into the future. Also, a common reason of witnessing many lightly raced horses often disappoint in the Derby as they have yet reached their full potential.

On the other side, we only have to go back into the past twenty years to bring-up some names of Kentucky Derby winners that never produced too much "after" getting their picture taken with a blanket of roses. Horses like Big Brown, Super Saver or even 2019's Country House, who benefitted from the rare disqualification of Maximum Security didn’t accomplish superstar status beyond their big victory under the twin spires.

The pattern is usually the same for their owners. Retire them before the year ends to enhance their breeding value. In essence before it potentially diminishes by any future defeats. 

#2 - Trainers DO Matter

Yes, every old cliché’ will repeat "horses" run on the track, not horse trainers or jockeys. But take a scan over the past 30 years and 90% of the time the top U.S. trainers end up in the winner's circle. Only with rare exceptions, like in 2009 when obscure trainer Bennie Wooley Jr. pulled off a shocker with Mine That Bird did a relatively unknown and unheralded trainer in thoroughbred racing earn a victory.

Perhaps we could also add 2014 to the list when California-based trainer Art Sherman won with Triple Crown candidate California Chrome. But other than that, only the most known names in the sport including Bob Baffert, Todd Pletcher, Bill Mott, and Doug O'Neill earn an opportunity.

The reason is quite simple. These successful trainers are tied to the most powerful stables, who breed the most expensive yearlings, set-up to be the most likely Kentucky Derby candidates.  Yes, it is possible for an inexpensive colt to make it to the big dance but not likely. Trainers like Baffert and Pletcher are expected to have top contenders in the starting gate, year after year.

Alright, on a brighter note, here is the field (with jockeys, trainers and starting odds) for the Run for the Roses this Saturday, May 1st along with my top three selections:

PP Horse Trainer Jockey ML Odds
1 Known Agenda Todd Pletcher Irad Ortiz Jr. 6-1
2 Like the King Wesley Ward Drayden Van Dyke 50-1
3 Brooklyn Strong Daniel Velazquez Umberto Rispoli 50-1
4 Keepmeinmind Robertino Diodoro David Cohen 50-1
5 Sainthood Todd Pletcher Corey Lanerie 50-1
6 O Besos Greg Foley Marcelino Pedroza 15-1
7 Mandaloun Brad Cox Florent Geroux 15-1
8 Medina Spirit Bob Baffert John Velazquez 15-1
9 Hot Rod Charlie Doug O'Neill Flavien Prat 8-1
10 Midnight Bourbon Steve Asmussen Mike Smith 20-1
11 Dynamic One Todd Pletcher Jose Ortiz 20-1
12 Helium Mark Casse Julien Leparoux 50-1
13 Hidden Stash Vicki Oliver Rafael Bejarano 50-1
14 Essential Quality Brad Cox Luis Saez 2-1
15 Rock Your World John Sadler Joel Rosario 5-1
16 King Fury Kenny McPeek Brian Hernandez Jr. 20-1
17 Highly Motivated Chad Brown Javier Castellano 10-1
18 Super Stock Steve Asmussen Ricardo Santana Jr. 30-1
19 Soup and Sandwich Mark Casse Tyler Gaffalione 30-1
20 Bourbonic Todd Pletcher Kendrick Carmouche 30-1



Difficult to leave the Derby favorite out of consideration, but perhaps for personal reasons I am rooting for this guy to lose.

It was announced on Tuesday that known thoroughbred owner and publicity hound Jim "Mattress Mack" McIngvale is planning to bet at least $2 million to win on Essential Quality. Another stunt to hedge covering the costs of a furniture promotion underway at his Gallery Furniture stores. It is believed that McIngvale's bet will be the largest ever placed on the Derby or any U.S. horse race.

With horse racing being a pari-mutuel wagering sport, it will kill or at least hurt the odds of anyone hoping to pin their action on Essential Quality. Not that the undefeated horse shouldn't be discounted, it just makes for poor value. The other thinking is it enhances betting opportunity for the other nineteen in the field.

As he has cooked-up similar deals with big bets for the World Series and Super Bowl, this time McIngvale is launching the "Kentucky Derby Fave Wins, You Win" promotion. Anyone buying a mattress that costs $3,000 or more will receive a 100% refund if Essential Quality wins. 

On the track Essential Quality has survived at least three trouble trips and still managed to win all five starts.  Here’s hoping he somehow runs out of luck in his sixth start.



Has the perfect Derby-like style to win the race assuming he breaks well and stays out of trouble. Likes to sit right off the pace and then turn it on into the stretch.

Owned by Juddmonte, one of the largest stables in the world, this is trainer Brad Cox’s other runner in the race (Essential Quality the other), who might be getting overlooked.  Horseplayers are often from the “what have you done for me lately” mentality, which will undoubtedly improve the price on Mandaloun.

Figure anywhere from 12-1 to 18-1 on a horse that probably would have been 5-1 if he won the Louisiana Derby. In that race six weeks ago, he was a mysterious sixth as the 6-5 favorite.  Look for very capable jockey Florent Geroux to turn it around with a much better effort, seeking his first win in the Derby. 



Talk about value. He only lost by a very tough neck to Essential Quality in the Blue Grass Stakes at Keeneland on April 3.  A winner of two of five races and no more than a length back in his career, the only question is the extended mile and a quarter distance.

Hall of Fame jockey Javier Castellano also will be “highly motivated” as he has won every U.S. race possible except the Kentucky Derby.  Neither has superstar trainer Chad Brown, seeking a big win for his number one client Klaravich Stables.

The key is the start of the race where it expected for Castellano to make a big move toward the front from the difficult 17 post position.  Should he clear that obstacle, it is a matter of pace and stamina, as Highly Motivated could even be on the lead. If he or another horse sets a reasonable first six furlongs, look out. 

Expect excellent value odds for a few reasons. Bettors have been backing off Castellano a bit because he has not returned to his Hall of Fame form since returning from surgery in February. Also, in a twenty-horse field, there simply are extra options to consider, not found in a traditional race.

**Win or lose, it will be great to feel the unique energy and excitement return to Churchill Downs this year for the Kentucky Derby.  Back to where it belongs on the schedule in the First Saturday in May.  Post time is scheduled for 6:57 PM EST.  Good luck…

Glenn Greene covers the games from a betting angle every week exclusively at For weekly betting insights, including previews and picks from Glenn, click here.

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