Sleeper Picks for the 2021 Kentucky Derby

| April 30, 2021 10:13 am PDT

The 147th installment of the ever-hyper Kentucky Derby touches down at Churchill Downs on Saturday, May 1st.

Most will flock to bet on Essential Quality, who looks like a deserving favorite, yet offers pretty good betting value at +275 at top Kentucky Derby betting sites.

If you want to bet on the Kentucky Derby and the plan is to play it safe, rolling with Essential Quality in some capacity looks like a good approach. Most of the respected Kentucky Derby betting experts predict this to be Essential Quality’s race to lose, and it’s hard to refute the logic.

That said, nobody ever looked at a horse race with the hope of making money and stopped at the popular bet. There is still major money to be made in a potential upset; the question is which horses can get it done?

If you’re wondering that – and you’re ready to place a bet – join me as I go over some of the best sleeper picks that could win the 2021 Kentucky Derby.

Highly Motivated (+1200)

In the interest of offering legit Kentucky Derby sleepers, I’ll start the pricing at +1000 or higher.

That isn’t to say contenders like Known Agenda (+750), Rock Your World (+475), and/or Hot Rod Charlie (+800) can’t stage the upset or don’t offer value – they can, and they do.

The goal is to achieve a bit more upside for bettors, if possible, and that plight may very well start with Highly Motivated. You can find the three-year-old colt at a cool +1200 price at Bovada, and you might want to take the Chad C. Brown trainee seriously.

Highly Motivated took second to only Essential Quality at the 2021 Blue Grass Stakes, and he has two wins on his resume. Finishing runner-up at a big race to the Kentucky Derby favorite is obviously what pulls me in and look at how close it was.

That doesn’t tell bettors Highlight Motivated will beat out a full field of capable horses, but my goodness.

If we’re not circling Highly Motivated as a potential upset special at the 2021 Kentucky Derby at this price, what are we even doing?

Medina Spirit (+1400)

Hey, here’s a fun game; let’s not even consider betting on the only horse Bob Baffert has in the Kentucky Derby.

Sound like a good idea? Yeah, I didn’t think so.

Baffert admittedly doesn’t come to the show with a favorite or even a horse widely regarded as a top challenger, but overlooking Medina Spirit feels like a mistake.

The value is too obvious considering the pedigree here, as Baffert quarterbacked the 2020 Kentucky Derby winner, and he’s locked up three wins here just in the past six races alone.

You can’t ignore Baffert’s presence, but Medina Spirit has also been flat-out competitive. The three-year-old colt has zero finished outside of second place and won the Robert B. Lewis Stakes.

He has two wins under his belt and finished runner-up at major events like the San Felipe Stakes and the Santa Anita Derby.

Even if you don’t want to go all-in on Medina Spirit, this is at least a horse we need to consider to place this weekend.

Mandaloun (+2200)

You can’t cross off the 2021 Risen Star Stakes winner off the betting card too quickly.

Mandaloun faded terribly at the 2021 Louisiana Derby, but that’s less disappointing the more you look at the competition in that race.

It only gets more daunting as the 2021 Kentucky Derby approaches, but the feedback has been nothing but positive.

With Mandaloun supposedly training well and looking sharp, it’s worth wondering if he can return to the form that stole the show at this year’s Risen Star.

If so, he’s mispriced when looking at his +2200 Kentucky Derby odds.

O Besos (+2800)

Things get a bit more interesting with O Besos, who is known for his ability to rally. You never want to be at the back of a race, but it’s not so worrisome when you can kick things into another gear.

O Besos has that ability to do that, and he also has two wins to his name. Beyond that, he performed fairly well at the Risen Star Stakes (4th) and took third at this year’s Louisiana Derby.

Fellow Kentucky Derby alum Mandaloun won the Risen Star Stakes, while O Besos was only behind Hot Rod Charlie and Midnight Bourbon (two horses with better odds at the KB) in the Louisiana Derby.

The results haven’t been perfect, but Besos has either gotten the job done or at least been in the thick of it for most of his races. It’s not likely that he emerges as a late-race spark to shock the world this weekend, but it’s also not impossible.

Sainthood (+4500)

This is admittedly a bit of a reach, but this post isn’t called 2021 Kentucky Derby sleepers for nothing. You want some real bang for your buck, and you want a horse you can believe in.

At some point, you also need to break away from the fringe +1000 priced horses and swing for the fences.

Not many longshots deserve your attention, but this Todd Pletcher trainee probably does. Sainthood has very appealing odds for a well-trained and inexperienced colt that nobody really knows much about.

Inexperience can be problematic, but all Sainthood has done is compete. Here’s how he finished in his recent three races in 2021.

  • 2nd
  • 1st
  • 2nd

One win won’t get you too excited, but one of those losses came to Like the King, who at least also has a (slim) shot in this weekend’s race.

Sainthood has some of the best training in the world, he’s a relative newcomer that could surprise, and he’s a fantastic price. Pletcher has been known to come out of nowhere to shock before, and at +4500, willing bettors could take a stab at him doing it again.

Betting on the 2021 Kentucky Derby

There you have it – some of my favorite sleeper picks for the 2021 Kentucky Derby. The problem with Kentucky Derby sleepers, though? They usually don’t amount to much.

You’re best off just rolling with the favorite here or targeting one of the popular challengers. Historically, at least, that’s been the best path to success when betting on the Kentucky Derby.

That said, upsets happen in horse racing all the time. Horses drop out, they get hurt, or they simply under-perform.

Even if you’re high on Essential Quality, it has to be unnerving when you go back and look at the tape of that insanely close win over Highly Motivated.

I’d start my search for the best 2021 Kentucky Derby sleepers there, but perhaps more than anything, that may create enough reasoning to look beyond the favorite this year.

My gut says Essential Quality lives up to the billing as the favorite and gets the job done. It’s an undefeated horse that has at least proven capable of edging out other horses even when its back is against the wall, after all.

But if you want to get away from the top threats to win the 2021 Kentucky Derby, my sleeper picks will help give you viable options to turn to.

For more insight on how to bet on this year’s Kentucky Derby, check out our elite horse racing betting analysis at our Kentucky Derby betting blog.

Noah Davis
Noah Davis

Noah Davis is one of the more diverse writers at Like many of his colleagues, he's a huge fan of both football and basketball. But he also writes about box office records, TV show prop bets, DFS, and all kinds of other subjects.

When it comes to the NFL, Noah's favorite team is the Cleveland Browns. He enjoys cheering them on with his wife and daughter.

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