2021 Kentucky Derby Betting Guide

Kentucky Derby

The 2021 Kentucky Derby has just about arrived, with all the action set to take place in the early evening on Saturday at Churchill Downs in Kentucky. 20 of the finest thoroughbred horses in the world are set to do battle in what should be a thrilling race. And we’re here to help you make your wagers at top Kentucky Derby betting sites with this extensive betting preview.

After the draw on Tuesday morning, we now know who will be in the field of 20 that will go to gate on Saturday. We also know the post positions for each of the horses, which obviously could affect the wagering on some of the key horses in the race. As far as the morning line favorite, Essential Quality, in no surprise at all, assumed the mantle at 2-1, which are relatively low odds for a favorite in a 20-horse field.

That last bit is part of what makes the Kentucky Derby such an interesting race to bet. It’s pretty much the only American thoroughbred races that you’ll see all year long with that many horses in the field. As a result, positioning will be crucial for the horses who want to have a chance to win the Run for the Roses.

Finding the Value

What 20 horses also means is that the Kentucky Derby is one of the best races in all of horse racing if you’re looking to find betting value. The sheer math of it ensures that there will only be a few horses with single-digit win odds. Most of the field will technically be long shots, even though every one of them had to achieve an impressive record to this point in their careers just to make the field.

When you make your wagers for the Kentucky Derby, always do it with the idea of value in mind.

Try to find the horses who are being underestimated at the odds board. And, if you do like some of the favorites, consider putting them in with some longer shots on some of your exotic (exacta, trifecta, superfecta, etc.) wagers.

We’re here to help you out with all of that by giving you this 2021 Kentucky Derby betting preview. In this article, we’ll take you through every one of the 20 horses in the field and tell you what we think their chances are. And we’ll end it all by giving you our picks for the top four finishers in the 147th Kentucky Derby.

2021 Kentucky Derby Details

Where: Churchill Downs in Louisville, Kentucky
When: Saturday, May 1, 2021, post time approximately 6:57 PM ET, race 12 on the Churchill program
Who: 20 3-year-old horses
Distance: 1 1/8 miles
Surface: Dirt
Purse: $2 million

2021 Kentucky Derby Betting Odds

Horse
BetUS Logo
MyBookie Logo
Bovada Logo
Essential Quality
+200
+300
+275
Rock Your World
+500
+550
+475
Known Agenda
+600
+750
+750
Hot Rod Charlie
+800
+900
+800
Highly Motivated
+1000
+850
+1200
Mandaloun
+1500
+1800
+2200
Medina Spirit
+1500
+1400
+1400
Dynamic One
+2000
+2400
+3500
King Fury
+2000
+2500
+4000
Midnight Bourbon
+2000
+1800
+2200
O Besos
+2000
+2500
+2800
Bourbonic
+3000
+3500
+4000
Soup and Sandwich
+3000
+4000
+2500
Super Stock
+3000
+2000
+2500
Brooklyn Strong
+5000
+5000
+5500
Helium
+5000
+4000
+5000
Hidden Stash
+5000
+4500
+5000
Keepmeinmind
+5000
+5000
+6500
Like the King
+5000
+4000
+6000
Sainthood
+5000
+3000
+4500

Shrink | Expand

The 2021 Kentucky Derby Field

#1 Known Agenda (Irad Ortiz, Jr., Todd Pletcher) 6-1

Trainer Todd Pletcher, who leads the Kentucky Derby field with four entries in 2021, has won the race twice before: With Super Saver in 2010 and Always Dreaming in 2017. Known Agenda seems like his best shot in this one. But he received the unfortunate draw on Tuesday, as the inside post in the 20-horse field is generally a terrible spot to be.
Known-Agenda-Horse

Pletcher tried to spin it to the media by saying that his horse has run on the inside before and performed well. Indeed, Known Agenda has flashed that ability in the past. But more important than that was the incredible flash he showed in the Florida Derby, traditionally one of the best Derby predictors, as hepowered past everybody on the final turn and drew away.

The vast improvement in this horse coincided with the switch to Irad Ortiz Jr. as the jockey. It is a bit concerning that he hasn’t gone further than 1 1/16 miles, which means he gets 3/16 of a mile added to his burden here. But Known Agenda certainly comes into the race off one of the more impressive efforts of all the preps.

Outlook:

Even with the rough post, don’t throw him away automatically.

#2 Like The King (Drayden Van Dyke, Wesley Ward) 50-1

Here is another case where a jockey switch seems to have ignited a horse, in this case literally propelling him into the Kentucky Derby. Wesley Ward handed the reins over to Drayden Van Dyke on Like The King in his last start, the JR Steaks at Turfway. And despite a rough journey, the colt kept coming and eventually scored the win in that Grade 3 event.

That Makes Him One-for-One In Graded Stakes Tries

The fact that he was only bet at 7 to 1 in that race indicates that he should be huge odds for the Derby. You just have to decide if Like The King is worth a long shot stab at a minor award so that you can include him in your exotics.

There is a decent amount of front-end speed in the race, which could mean there’s some possibility of deep closers being a factor. Look for Van Dyke to settle inside and save ground with Like The King early. From there, it’s just a matter of whether he’ll be close enough when he makes his late move to actually get somewhere into the picture.

Outlook:

Something like a fourth-place finish is the best he can hope, as the class just isn’t there.

#3 Brooklyn Strong (Umberto Rispoli, Daniel Velazquez) 50-1

The hope here is that this colt, who snuck into the field, can use the angle of second start off a long layoff to possibly push him into the mix. There is definitely class there, as Brooklyn showed off during his two-year-old season. That was when he churned out three wins in four races, with victories at Delaware, Belmont and Aqueduct.

The last of those wins came in the Grade 2 Remsen and was even at the distance of 1 1/8 miles, which proved he was ready for longer races even at a younger age. But then injuries cropped up, and Brooklyn Strong was largely sidelined for the first part of his three-year-old season while others were racking up prep points. It was only last month that he made his first start of ’21 in the Wood Memorial.

Perhaps it was no shock when he ran a listless 5th in a race won by Bourbonic. Even if he takes a big jump off of that, that race wasn’t one of the most stacked Derby preps. And sometimes the second start off the hiatus isn’t the peak when the layoff is as long as the one endured by Brooklyn Strong.

Outlook:

There just isn’t enough on the books to make him a worthwhile long shot pick.

#4 Keepmeinmind (David Cohen/Roberto Diodoro) 50-1

In his pedigree is the name Victory Gallop, who was one of the best way-back closers in recent memory. Keepmeinmind largely employs that style, and that’s not always a bad thing in the Kentucky Derby. After all, others in the field will be feeling the effects of the 1 1/4 -mile distance, while this one might just be getting warmed up at that point.

None of that matters though if a horse is two football fields behind when it starts to get in gear. And that’s the fear with Keepmeinmind, that the field might leave him behind because of his sluggishness at the start. In his two starts this year, that’s been the case, as he ended with fifth and sixth place finishes.

To his credit, Keepmeinmind has faced one of the toughest schedules of anybody, with nothing lower than a Grade 2 since he won his debut. But his speed figures this year haven’t been a patch on what he did a year ago. He’ll have to wake up the echoes of his two-year-old season even to make it into the exotic picture.

Outlook:

Use him at the tail end of your exotic tickets at most, but don’t go farther.

#5 Sainthood (Corey Lanerie, Todd Pletcher) 50-1

With only three races under his belt and a second in his only graded stakes effort, this one seems like a shot in the dark for Todd Pletcher. There have been horses as lightly raced who’ve gone on to Kentucky Derby glory. But those horses also showed a lot more in their brief pre-Derby careers than Sainthood has to this point.
Sainthood-Horse
There are some interesting names in his pedigree that suggest this horse might have a trick or two up his sleeve. If anything, the inexperience might make him more of a long shot lure. The logic would be that Sainthood still hasn’t figured it out, but if the light comes on Saturday, he could be a big value play.

His trip in the JR Steaks, where he came up short behind Like The King, wasn’t the best, which suggests that racing luck could help him improve. It’s just hard to see a Grade 3 competitor leapfrogging the ones who have been seasoned against much tougher company. You can probably afford to look elsewhere than Sainthood, even with your deep long shot plays.

Outlook:

Watch him later in the season, but he’s not ready yet.

#6 O Besos (Marcelino Lopez, Greg Foley) 20-1

Even though he was only a $10,000 purchase, O Besos does come directly from a Derby champion, as his daddy Orb won the Run for the Roses in 2013. This colt made the field against expectations. Despite being a long shot in both of his graded stakes this year, his minor awards were enough to punch his ticket.

The good news is that he seems to be improving each and every race if you believe the speed figures. And that improvement will have to continue for his Derby changes to be even remotely realistic. After all, there are three horses in this field who finished ahead of him in those last two races, including one who did it twice (Midnight Bourbon.)

O Besos will also be closing, or at least attempting to, as the Kentucky Derby field turns for home. There are a lot of those types of horses in the field, which means that they all can’t be in the mix once other horses tire. But it’s not out of the question that this one sneaks in for a third of fourth.

Outlook:

Another one for your Tri’s and Super’s and nothing more.

#7 Mandaloun (Florent Geroux, Brad Cox) 15-1

His stablemate Essential Quality is going to steal all the press in the runup to the Kentucky Derby. But this other Brad Cox trainee could be just as much of a factor in the race if he can bounce back from a bad effort. At his peak performance level, Mandaloun can certainly hang with anybody in this race.

It’s always tough for handicappers to throw out a clunker of a race, like the one Mandaloun had in his last start in the Louisiana Derby. But in a race like the Derby, you’ll want to narrow it down to the horses who you could conceive of winning. And Mandaloun might have the most lucrative morning line odds when you’re talking about those horses.

Two races ago, he was stellar in the Risen Star from an outside post in a field of ten. Maybe his lackluster effort in the Louisiana was a portent of things to come, or maybe it was a race where Mandaloun just didn’t have his “A” game. We’ve seen that his “A” game is enough to win the Kentucky Derby, so don’t discount him.

Outlook:

Expect his odds to drop as savvy bettors salivate at the potential of an upset winner.

#8 Medina Spirit (John Velazquez, Bob Baffert) 15-1

How is it possible that Bob Baffert only has one entrant in the 2021 Kentucky Derby? Racing can be a tough sport, even on the all-time trainer, who has six Derby wins to his credit. To bolster his chances of a lucky seven, he has the services of John Velazquez, who has won this race three times in the last decade himself, aboard Medina Spirit.

Here Is the Thing With Medina Spirit:

You’re just not going to get a fair price on him. Every casual racing fan who knows nothing about the sport except the ubiquitous sight of Baffert’s white hair will take a stab at him to win, bringing his odds down well below where they should be. If this colt were in the barn of any other trainer, he’d be just another horse in the field and you might get some value at him.

Medina Spirit still had to earn his way into the field. But he did it by finishing second in his last two a combined 12 ¼ lengths behind the race winners. There is a consistency of effort that’s encouraging, but the low ceiling and his frontrunning racing style don’t bode well for him in here.

Outlook:

It’s not Baffert’s year, at least not in this race.

#9 Hot Rod Charlie (Flavien Prat, Doug O’Neill) 8-1

Can this colt take advantage of good getaway speed to put this field to sleep? That’s what he did in the Louisiana Derby, taking control early despite an early bump and covering the 1 3/16 miles with no sweat. Hot Rod Charlie was actually going away from the field by the end of the race for a 2-length win.

That was a slight change in strategy, as he had never gone out on the front end before in a previous race, although he had stalked the pace from close behind a few times. The question is whether new jockey Flavien Prat, who won the Derby with Country House two years ago after the infamous Maximum Security disqualification, will make that same early move with Hot Road Charlie. He is taking over as jockey for trainer Doug O’Neill, who is looking for his third Derby win.

Hot Rod Charlie had shown flashes before that victory, including a second place at 94-1 in last year’s Breeders’ Cup Juvenile. The post position is pretty solid if he does choose to leave. Those middling odds could be quite tempting for those who don’t want to settle for the chalk.

Outlook:

If Prat can rate the pace, he could be hanging around at the end.

#10 Midnight Bourbon (Mike Smith, Steven Asmussen) 20-1

Trainer Steven Asmussen is one of the top trainers who has never won a Kentucky Derby to this point. But he certainly gave himself a shot by choosing Mike Smith, long considered one of the best big-race jockeys, for Midnight Bourbon. This will be the two-time Derby winner’s first time aboard this colt who has never missed the board in seven career races.
Midnight-Bourbon-Horse
Midnight Bourbon was purchased for a hefty price as a yearling, but has never really earned too much respect from bettors. He hasn’t been favored in any of his five races since his maiden win at Ellis Park last August. And for the most part, the bettors have been right, as he has only won one of those five races, even as he has been in the money every time.

There are two ways to look at near-miss horses. Either you can believe that they just need luck to break through, or you see a trend in their inability to go that little extra bit to get the win. In the case of Midnight Bourbon, it’s starting to feel like a little bit of the latter.

Outlook:

He has been outfinished late by others in his last two, which could happen again on Saturday.

#11 Dynamic One (Jose Ortiz, Todd Pletcher) 20-1

In his last start in the Wood Memorial, this Todd Pletcher trainee got away at 15 to 1, which was understandable considering that he had only just moved up to graded stakes action. After a pretty impressive drive, he found himself staring down the wire, only to get caught by the furious rally of the even longer shot Bourbonic. Now Dynamic One tries to improve off that.

For those who believe in the purchase price being an indicator, Dynamic One went for three-quarters of a million dollars back when he was a yearling. But truth be told, the results haven’t come close to matching that until that effort in the Wood. And even then, he was beaten by a bomber, which doesn’t make it look like one of the better preps.

The connections are good, of course, and long shot winners are certainly a part of the Derby. But the likelihood is that Dynamic One could easily drop back down in terms of form off that peak effort last time around. There just isn’t a lot of meat on the bone in his lines to choose him over some of the others in here.

Outlook:

Maybe he peaked one race too soon.

#12 Helium (Julien Leparoux, Mark Casse) 50-1

In terms of the path it takes a horse to get to the Kentucky Derby, this son of Ironicus has certainly tread one. As a two-year-old, Helium picked up a pair of victories to start his career at Woodbine in Canada. That isn’t traditionally a launching ground for possible Triple Crown winners.

Both of those wins came at seven furlongs, but when Helium returned to action in the Tampa Bay Derby in March, it was at the two-turn distance of 1 1/16 miles. Bettors were understandably unimpressed and let him go at 15-1. But he worked his way up out wide from a 10 post in a field of 12 and kept after it until he took over in the stretch for the win.

He did defeat Hidden Stash, who is also in the Derby field, in that race, but overall it wasn’t the most competitive Derby prep. Still Helium is undefeated, joining favorite Essential Quality and Rock Your World as the only horses in the field to hold that distinction. His first defeat is probably coming, but he’s a great story nonetheless.

Outlook:

Expect the air to go out of the Helium balloon.

#13 Hidden Stash (Rafael Bejarano, Vicki Oliver) 50-1

This colt sired by Constitution is the rare horse to have been claimed who has made it to the Kentucky Derby. That happened when Hidden Stash was a two-year-old and was picked out of a $75,000 optional claimer that he won at Churchill Downs. He then vaulted up into graded stakes company for his three-year-old season, where he’s earned over $189,000, making that claim look pretty good.

That Doesn’t Mean Hidden Stash Is Ready to Compete On This Level

Of those three graded stakes races, his best effort was a second in the Tampa Bay Derby, which saw him losing to the upstart Helium. He followed that up with a distant fourth in the Bluegrass in a not-so-triumphant return to his old Kentucky stomping grounds.

Hidden Stash prefers the kind of swooping move that starts on the back stretch and, ideally, sees him out in front at some point at the top of the stretch or shortly after. But he doesn’t seem to have the power to execute that kind of swoop against Grade 1 level runners. As a result, he’ll probably stay hidden on Saturday.

Outlook:

Almost certainly one of the also-rans

#14 Essential Quality (Luis Saez, Brad Cox) 2-1

The unbeaten favorite dodged a bit of a bullet with the draw, as he very nearly got pinned on the inside where Known Agenda ended up. So far in his career it’s pretty hard to find a flaw. Essential Quality has picked up wins in every one of his five starts, and in every one of those he has been separating from his closest pursuit at the end, which bodes well as he takes on the extra distance in the Derby.

In addition, there is just a gameness about him which all the great champions tend to have. It showed in the bluegrass when he took the best shot of Highly Motivated and won a grueling stretch duel. The pedigree is there, trainer Brad Cox is on fire, and jockey Luis Saez is motivated to exorcise the demons hanging around him ever since the controversial Maximum Security ride two years ago.

If there is a small hitch with Essential Quality, it’s that he sort of dodged the biggest prep races. Could that leave him without the seasoning he needs against this sternest of tests? It’s enough of a seed of doubt to make those short odds far from compelling for value players.

Outlook:

He very likely could cash as the favorite, but the bang for your betting buck isn’t there considering he’s no sure thing.

#15 Rock Your World (Joel Rosario, John Sadler) 5-1

The last of the unbeaten horses in the race is a colt who will be ridden by Joel Rosario for the first time, giving Rock Your World the privilege of a Derby winner aboard (Rosario won in 2013 with Orb.) It was an interesting call for trainer John Sadler, as Umberto Rispoli had been the jockey for the first three victories of this horse’s career. That is a big dice roll, but if you’re not going to gamble on the Derby, when will you ever?
Rock Your World
Rock Your World has taken a somewhat unorthodox journey to get here, as he has only one dirt start in his career. Unraced as a two-year-old, he conquered two turf fields at Santa Anita to get rolling in 2021. That’s when Sadler went after the dirt prize of the Santa Anita Derby and the colt rose to the occasion, leading at every pole for a dominant 4 ¼-length win.

Should he decide to go to the front, there aren’t a ton of horses that might challenge him, which is a good thing considering the post. Rock Your World also showed stalking tendencies in one of his turf wins, so there is a possibility he could adjust. The feeling here is that the ceiling might be just as high as the one for Essential Quality, only at a much more lucrative price.

Outlook:

If the jockey switch takes, you could be looking at the winner.

#16 King Fury (Brain Hernandez Jr., Kenneth McPeek) 20-1

It takes only one start for a horse to really vault itself into the Kentucky Derby picture, and that was the case for this Kenneth McPeek trainee. King Fury raced five times as a two-year-old, and although he was a two-time winner, he really struggled in his three graded stakes efforts. His handlers decided a break was in order, so the colt sat out for the first few months this season.

Without much in the way of an impressive record, he understandably didn’t get too much betting love when he came back in the Grade 3 Lexington three weeks ago. Yet King Fury maneuvered his way through the slop at 18-1 for a pretty comfortable come-from-behind victory. And all of a sudden, a Derby contender was on the map.

The fact that the win came in sloppy conditions is a bit of a red flag, as it raised the possibility that the win was a bit of a fluke. In the positive department, it was the first start off a layoff for King Fury, so there is a possibility that he could be even better at the Derby in his next go around. But it seems too much of a leap for him to go from so far off the map into glory so quickly.

Outlook:

There are better long shots to play.

#17 Highly Motivated (Javier Castellano, Chad Brown) 10-1

The speed figures seem to love this colt, even though he doesn’t have any wins this year to show for it. His first start in 2021 saw him overcoming a bobbling start early on his way to a close third at Aqueduct. Then came the real eye-opener, as Highly Motivated absolutely pushed Essential Quality to the hilt in the Bluegrass Stakes at Keeneland before finally succumbing in the last strides.

It’s a little bit worrisome that he is building his Derby case on a pair of losses, especially if you’re going to take this one on top. One key here will be a style adjustment for Highly Motivated, as he isn’t likely to win on the front end from a #17 post. Jockey Javier Castellano, who is still looking for that first Derby win to put the icing on top of an impressive career, will have to be quite crafty, as this post is generally a dead zone.

Those who swear by the analytics will probably overlook all of that and go with Highly Motivated anyway. But the value isn’t superb considering all he has to overcome with the post and the fact that he hasn’t won since last year. There are other contenders who don’t have those obstacles who will get you better prices.

Outlook:

Not out of the realm of possibility, but not worth a bet unless those odds rise a little.

#18 Super Stock (Ricardo Santana Jr., Steven Asmussen) 30-1

Once you get outside of that #17 spot, you really have to weight the post positions against the horses who are in those far-out spots. So that’s immediately one strike against this son of Dialed In who joins Midnight Bourbon from the Steven Asmussen barn for this race. With eight starts under his belt, Super Stock certainly doesn’t lack for experience, although most of it was somewhat mediocre until his last race.

That’s when he went out at 12-1 in the Arkansas Derby and raced with a different level of confidence and potency. He tracked the leaders and then whipped off the cover full of horse, blowing past the few in front of him to win by a comfy 2 ½ lengths. But the post position might be a real hindrance to him, perhaps more than the others way on the outside.

To this point, Super Stock has endured just three races with a post position any further out than #4. And in those three starts, he has managed just one finish in the money, while he was up the track in the other two. We’re talking #7, #8 posts here, not #18, which is going to make the past of following up that career-best performance quite difficult.

Outlook:

He already had his moment in the sun in Arkansas.

#19 Soup And Sandwich (Tyler Gaffalione, Mark Casse) 30-1

Another latecomer to the Derby scene, this colt was bred for big bucks but then took a while to get out to the races for trainer Mark Casse. But once he got out there as a three-year-old, Soup And Sandwich started making up for lost time. First came a romping win in his debut at Gulfstream at 6 ½ furlongs, a performance that begged for a move to a longer distance.

Next up was his first two-turn try in an optional claimer at Tampa Bay, a test which he handled pretty easily. But stepping up into the hot spotlight of the Florida Derby seemed like a huge jump to make, at least until he battled his way to a second-place finish. Although Known Agenda separated from him late, Soup And Sandwich gamely held onto the place at 12 to 1.

With John Velazquez choosing off, trainer Mark Casse is going with Tyler Gaffalione for the Derby mount. And Gaffalione will be put to the test by the post position, as he tries to reconcile the speed-favoring style of Soup And Sandwich with the 18 horses starting to the inside of him. He may have no choice but to try for the lead, but the other speed horses will probably park him out.

Outlook:

There is a nice future in store for him, but he’ll be left hungry on Saturday.

#20 Bourbonic (Kenrick Carmouche, Todd Pletcher) 30-1

Trainer Todd Pletcher probably has to wonder what racing gods he angered to have horses stuck on both extremes post-position wise, as Bourbonic has the far outside to go with Known Agenda deep on the rail. In many ways, the far outside is a little bit preferable to the spots just to the inside, if only because the horse out there isn’t pinned on both sides. That won’t make it easy for the colt, but he’s already overcome a lot just to get here.
Bourbonic Horse
This is a horse who was claimed not once, but twice in the early part of this year. He wound up in the lineup for the Wood Memorial and was unceremoniously let go at 72 to 1. The fact that he’s in the field is the spoiler to this story: Bourbonic came from dead last halfway through the race to nail Dynamic One at the line in a stunner.

Jockey Kendrick Carmouche’s decision to hold the colt way off the pace in the Wood, instead of stalking as he’d done in his previous races, seems to have ignited him. He’ll most likely do the same on Saturday, shuffling him in as quickly as possible, saving ground, and then hoping Bourbonic can unleash late. Putting another stunner up on the board seems like a script that even Hollywood wouldn’t dare to write.

Outlook:

Probably coming up late but not close enough for minor awards

The Pick for the 2021 Kentucky Derby

The Tuesday draw likely claimed Known Agenda; if the field were a bit shallower, overcoming the rail might be possible, but this is a stout group of 20. As for the favorite Essential Quality, the last race was a bit of a concern, as game as he was. A 2-1 morning line Kentucky Derby favorite really should have blown Highly Motivated away, but that didn’t happen.

Rock Your World, the second choice, therefore steps up in the pecking order. It feels like he can get out quick and dictate the pace, and he proved in his last at Santa Anita that he can definitely sustain that pace and then some. Look for Joel Rosario to step up big on the jockey switch and guide this one home for the victory at a decent price.

After that, Mandaloun is the long shot in which you should have the most shares. He’s a likely second-place finisher here, but you’d be wise to put him on top in some tickets at top horse racing betting sites as well. Look for Essential Quality for third, while Known Agenda’s excellent talent gets him as far as fourth even with the awful post.

2021 Kentucky Derby Superfecta Ticket –#15 – #7 – #14 – #1

Jim Beviglia

Jim Beviglia joined Gamblingsites.org as a staff writer in 2018, parlaying his years of freelance writing into contributions on a number of different topics. He handles the sport of horse racing for GamblingSites.org and the intersection between the worlds of cryptocurrency and online gambling in a weekly blog.
For his full-time job, Jim handles the television and track announcing duties at a h …

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