Analysis: How to bet Kentucky Derby 2021

The post-position draw for the 2021 Kentucky Derby is complete and the 2-1 morning line favorite Essential Quality drew post 14. That means it is time to make decisions about who you think will win the race and the wagers you will be placing on Saturday.

There are significant trends for the horse that crossed the finish line first on the first Saturday in May that have developed since the points system began in 2013. These criteria might help to focus your list of win contenders. Note the lone exception to these trends was last year when the Derby was postponed until September. Winner Authentic had run second in the Santa Anita Derby. 

• The first-place finisher had at least 100 qualifying points. In 2019, Country House had only 50 points when he was awarded first after the disqualification of first-place finisher Maximum Security who did exceed the 100-point barrier.

• They all won a 100-point prep race.

• All were undefeated in their races as a 3-year-old.

• Except for Orb in 2013, each of the horses raced forwardly – stalked the pace, pressed the pace or set the pace.

The 2021 Derby field has only two horses that check all four of those boxes. Read the analysis below to find out who they are.

There is only one Kentucky Derby, and it is the only race in our country with a 20-horse field. That large field provides unique opportunities for American bettors with payoffs in all exotics, both vertical and horizontal, being unusually large.

Playing the horizontal wagers – daily doubles and pick 3, 4 and 5s – means that you must identify the horse or horses that have a chance to win the Derby. In the vertical bets – exactas, trifectas or superfectas – you have the opportunity to key horses underneath; that is, in the second, third and fourth positions.

The 20-horse Kentucky Derby field exaggerates the odds of horses like no other race in America. Here is an analysis of the big race with an eye on which horses should be used to win in the horizontal bets or as part of the vertical wagers. The official morning line from Churchill Downs is listed with Derby points earned and last race result with its Beyer Speed Figure. The Run for the Roses is slated as race 12 out of 14 with post time scheduled for 6:57 p.m. EDT.

Known Agenda (6-1 – 102 – 1st Florida Derby (G1), 94 - Curlin - Irad Ortiz Jr. / Todd Pletcher - 6: 3-1-1 - $467,100) Known Agenda leads the four Todd Pletcher horses that are set to run. The trainer looks to win his third Derby. Known Agenda will try to take the same path to victory as Always Dreaming used in 2017 with wins at Gulfstream Park in an allowance followed by the Florida Derby before heading to Churchill Downs. There is no question that this son of Curlin is an improving 3-year-old and that his stalking running style will serve him well in the 10-furlong test. Win contender, top choice.

Like the King (50-1 – 104 – 1st Jeff Ruby (G3), 86 - Palace Malice - Drayden Van Dyke / Wesley Ward - 6: 3-2-1 - $200,680) This Wesley Ward runner began his career at Belterra Park, where he broke his maiden in his second start. It was on the Tapeta surface at Turfway Park that he found his own with two wins and a second. It seems that Like the King has been better than expected for Ward. It also might be a surprise to know that this will be Ward’s first Derby runner. Speed figures lag behind most of the field. Toss.

How to Crush the Kentucky Derby 2021 Superfecta

Brooklyn Strong (50-1 – 10 – 5th Wood Memorial (G2) – Wicked Strong – Umberto Rispoli / Daniel Velazquez – 6: 3-0-1 - $225,000) Brooklyn Strong had a great juvenile campaign with three wins from four starts, including the Remsen (G2) on the Derby trail in December. After that, it was one setback after another, which kept him from getting to the races until the Wood Memorial (G2), when he finished an uncompetitive fifth. The Derby is a tough spot to try to find a horse’s best performance. Toss.

Keepmeinmind (50-1 – 18 – 5th Blue Grass (G2), 73 – Laoban – David Cohen / Robertino Diodoro – 6: 1-2-1 - $172,624) After a promising 2-year-old campaign that included a maiden victory in the Kentucky Jockey Club (G2) at Churchill, his two starts this year have to be considered disappointing. He was not a factor in either the Rebel (G2) or the Blue Grass (G2), so it is hard to expect a reversal in form in the Derby. Blinkers come off. Toss.

Sainthood (50-1 – 40 - 2nd Jeff Ruby (G3), 84 - Mshawish – Corey Lanerie / Todd Pletcher - 3: 1-2-0 - $91,900) Sainthood is one of four Pletcher runners in the Derby field and, in a way, he might be the most interesting. Four times in his career, Pletcher started four horses in the Derby and each time at least one of them was part of the trifecta. On the dirt, Sainthood was second in his debut at Gulfstream Park and then broke his maiden on the main track at Fair Grounds. Pletcher put him in the Jeff Ruby on the Tapeta, where at odds of 10-1, he encountered traffic in the stretch, had to check and lost all momentum. He recovered quickly, got clear and closed a lot of ground to finish second beaten by only a length. Back on the dirt in the Derby, this guy will come with big odds and a chance to rally into the exotics. A must use in exotics.

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O Besos (20-1 – 25 – 3rd Louisiana Derby (G2), 96 – Orb - Marcelino Pedroza / Greg Foley – 5: 2-0-1 - $172,624) Two victories for O Besos came in a maiden special weight and then an allowance at Fair Grounds. He stayed in New Orleans for the final two Derby preps where he ran fourth in the Risen Star (G2) and third in the Louisiana Derby, in which he rallied from eighth and last when he was seven lengths behind. He is one of the buzz horses in the mornings at Churchill Downs. Use underneath.

Mandaloun (15-1 – 52 – 6th Louisiana Derby (G2), 82 - Into Mischief – Florent Geroux / Brad Cox - 5: 3-0-1 - $361,252) Mandaloun, the other Brad Cox horse in the race, was the impressive winner of 50 points in the Risen Star (G2) as the 2-1 favorite. He headed into the Louisiana Derby as the 6-5 favorite and came up empty to run sixth, which was the first off-the-board finish of his career. It’s hard to dismiss that kind of performance from a horse who has always shown up and run well. He will be one of many horses that has shown a preference to press the pace. Toss.

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Medina Spirit (15-1 – 74 –2nd Santa Anita Derby (G1), 94 - Protonico – John Velazquez / Bob Baffert - 6: 3-1-1 - $467,100) After all is said and done, Medina Spirit will be the lone Bob Baffert horse in the Derby field – no Life is Good, no Bezos, no Concert Tour, no Hozier – just this consistent son of Protonico who was second in the Santa Anita Derby. The large Derby field and the extra distance don’t seem to suit this Florida-bred colt, who won the Robert B. Lewis (G3) with a front-end effort in a blanket finish. He will get overbet because of Baffert’s six-win record in the Derby. Toss.

Hot Rod Charlie (8-1 – 110 – 1st Louisiana Derby (G2), 99 – Oxbow - Flavien Prat / Doug O’Neill - 7: 2-1-1 - $1,005,700) With his Louisiana Derby victory, Hot Rod Charlie lived up to the promise he flashed as a 2-year-old when he ran second as a long shot in the Breeders’ Cup Juvenile (G1). He used his speed to convincingly win that 100-point qualifier, which was run at 1 3/16 mile. Thus, Hot Rod Charlie is a winner at a distance longer than any other horse in the field. The Louisiana Derby was a fast race, much faster than the other Derby preps at Fair Grounds. He has victories at four tracks. Trainer Doug O’Neill is a two-time Derby winner with I’ll Have Another and Nyquist. Win contender.

Midnight Bourbon (20-1 – 66 - 2nd Louisiana Derby (G2), 96 - Tiznow – Mike Smith / Steve Asmussen - 7: 2-2-3 - $467,100) – This consistent colt picked up 66 points with a win in the Lecomte (G3) in January and then with a third and a second in the other Fair Grounds prep races. Midnight Bourbon was second in the Louisiana Derby going the 9.5 furlongs pressing the fast pace of Hot Rod Charlie and earned a big Beyer. He could get Asmussen another top three finish in the Derby. Use underneath.

Dynamic One (20-1 – 40 – 2nd Wood Memorial (G2), 89 - Union Rags – Jose Ortiz /Todd Pletcher - 5: 1-2-0 - $194,120) Dynamic One is the third Pletcher runner in the field, and this guy was handled with plenty of patience by his trainer. He faced tough fields in his early maiden races. In the Wood Memorial, he made a strong closing move, took the lead in the stretch and looked like a winner until his stablemate caught him at the wire. The connections were very high on this horse heading into his last race. He will have plenty of horses out front to set the table for his closing move. Win contender.

Helium (50-1 – 50 – 1st Tampa Bay Derby (G2), 84 - Ironicus – Julien Leparoux / Mark Casse - 3: 3-0-0 - $287,763) Helium has a career record of 3-for-3, as does Rock Your World, but there is a huge difference in their odds. Helium will try to win the Derby with only one start as a 3-year-old. It was a late-running win in the Tampa Bay Derby, where he closed from 10th to win at odds of 15-1. Immediately after the victory, trainer Mark Casse said that they would train up to the Derby, and that meant a two-month layoff. There will be plenty of pace to set up his closing move at big odds. Use underneath.

Hidden Stash (50-1 – 32 – 4th Blue Grass (G2), 82 – Constitution - Rafael Bejarano / Vicki Oliver - 7: 2-1-2 - $231,062) Hidden Stash passed tired horses in a trio of Derby preps and earned points in all three. He was third in the Sam F. Davis, second in the Tampa Derby, and most recently fourth in the Blue Grass. Doing that in the Run for Roses has allowed some long shots to sneak into the trifecta or superfecta, but this is a much tougher spot. Toss.

Essential Quality (2-1 – 140 - 1st Blue Grass (G2), 97 – Tapit – Luis Saez / Brad Cox – 5: 5-0-0 - $2,265,144) Essential Quality checks all of the boxes of a potential Kentucky Derby winner – more than 100 points earned on the Derby trail, a victory in a 100-point race, unbeaten as a 3-year-old and races close to the pace. He won his debut race at Churchill Downs and will be racing from his own stall. Yet he does not come with the buzz of the recent speedy Bob Baffert runners. There are experts that feel the 10-furlong Derby distance might be too much for a horse with a paddling left front leg. Still, a worthy Derby favorite and win contender.

Rock Your World (5-1 – 100 – 1st Santa Anita Derby (G1), 100 - Candy Ride – Joel Rosario / John Sadler - 3: 3-0-0 - $546,600) Rock Your World led the Santa Anita Derby every step of the way as he made his debut on a dirt track after winning his first two on the turf. He is the other horse that checks all four of the boxes of a Derby winner. He’s 3-for-3 in his career, with all of them run as a 3-year-old; totaled 100 qualifying points; has a victory in a 100-point prep race; and raced on the lead. The son of Candy Ride also is the only horse in the field with a three-digit Beyer in his most recent start. He gets Joel Rosario in the saddle. Win contender.

King Fury (20-1 – 20 – 1st Lexington Stakes (G3), 95 – Curlin – Brian Hernandez Jr. / Ken McPeek – 6: 3-0-0 - $262,739) King Fury made a rousting return to the Derby trail when he rallied from eighth, while 10 lengths behind, to win the Lexington by almost three lengths. His first two victories last year came as a maiden and then in the Street Sense at Churchill Downs. Remember, King Fury was a $950,000 purchase as a Saratoga yearling. He will get a favorable pace set-up for his closing move. Use underneath.

Highly Motivated (10-1 – 50 – 2nd Blue Grass (G2), 97 - Into Mischief - Javier Castellano / Chad Brown - 5: 2-2-1 - $320,050) Highly Motivated gets high marks for coming within a neck of defeating Essential Quality in the Blue Grass after setting all of the fractions. In defeat, however, he was far ahead of the rest of the field, which shows the quality of his performance. Trainer Chad Brown and rider Javier Castellano are both looking for their first Derby win. This son of Into Mischief joins the list of horses that want to be part of the early pace. Use underneath.

Super Stock (30-1 – 109 – 1st Arkansas Derby (G1), 92 – Dialed In - Ricardo Santana Jr. / Steve Asmussen - 8: 2-2-2 - $804,762) Super Stock got a perfect trip in his Arkansas Derby victory when he saved ground in the early going while tracking a fast pace. He swung outside and ran by the five other competitors to win easily. No horse gets a trip like that in the 20-horse field of the Kentucky Derby. Owned in part by trainer Steve Asmussen’s father, he is a feel-good horse for the Hall of Fame trainer who has a 0-for-21 record in the Run for the Roses. Toss.

Soup and Sandwich (30-1 – 40 – 2nd Florida Derby (G1), 90 - Into Mischief – Tyler Gaffalione / Mark Casse - 3: 2-1-0 - $203,875) After winning the first two races of his career, which began this year, this second Mark Casse Derby horse burst onto the scene when he ran second in the Florida Derby at odds of 12-1 as he pressed the pace and had the lead until being overtaken by Known Agenda. There is a long list of horses in this field with similar running styles, which will make it hard for handicappers to separate them. I can’t blame you if like this son of Into Mischief, but I like others more in the trifecta. Toss.

Bourbonic (30-1 – 100 – 1st Wood Memorial (G2), 89 – Bernardini - Kendrick Carmouche / Todd Pletcher - 6: 3-1-0 - $465,880) Even trainer Todd Pletcher was surprised by Bourbonic’s victory in the Wood Memorial at odds of 72-1. He was in that race because owner Brad Kelley of Calumet Farm asked his trainer to give the horse a chance in a points race. The son of Bernardini did have two wins at Aqueduct during the winter, so maybe he should have been more like 30-1 in the Wood. The Wood was run slowly, and he got a perfect trip. Toss.

Summary: The odds and analysis will be used to construct a horizontal wager in the Oaks/Derby two-day daily double and a vertical wager in the Derby trifecta.

That daily double combines a field of 14 in the Kentucky Oaks with the 20 horses in the Kentucky Derby. It is unusual for Todd Pletcher to use superlatives to describe one of his horses before they have won one of America’s marquis races. Yet, that is what he did calling Malathaat a “star.” I will single her in the Oaks with all of the Derby win contenders from above.

$10 Oaks/Derby daily doubles: Malathaat with Essential Quality, Hot Rod Charlie, Know Agenda, Rock Your World, Dynamic One. = $50

A horizontal wagering technique that I have used with success in the past in the Derby is to key a long shot in the bottom positions. Sainthood is going to be a very big price in terms of win odds, but he will also be a great value in the trifecta pools. I will use him in the second and third positions with my five win contenders. The wager is designed to produce a big payout especially if the favorite runs off the board. If you prefer a different long shot, then go ahead and key him instead of Sainthood.

50¢ trifecta part-wheel ticket 1: Essential Quality, Hot Rod Charlie, Know Agenda, Rock Your World, Dynamic One with Sainthood with Essential Quality, Hot Rod Charlie, Know Agenda, Rock Your World, Dynamic One, Midnight Bourbon, Highly Motivated, Helium, O Besos, King Fury = $22.50

50¢ trifecta part-wheel ticket 2: Essential Quality, Hot Rod Charlie, Know Agenda, Rock Your World, Dynamic One with Essential Quality, Hot Rod Charlie, Know Agenda, Rock Your World, Dynamic One, Midnight Bourbon, Highly Motivated, Helium, O Besos, King Fury with Sainthood = $22.50

For a more Kentucky Derby analysis, watch this week’s editions of HorseCenter, which will be posted on Tuesday and Thursday.