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2021 Kentucky Derby Picks, Predictions and Odds

 

Apr. 28, 2021

Horse Racing Expert
VegasInsider.com

147th Kentucky Derby Predictions

The 2021 Kentucky Derby field is all set and I've got my top picks and betting strategies set for Saturday's main event from Churchill Downs.

Listed below are my top four picks and predictions for 147th Kentucky Derby "If Things Go Well" and "If All Hell Breaks Loose."

Also, I've offered a quick snapshot of all the expected runners in this year's Triple Crown opener.

Enjoy and Best of luck!

Most Popular Kentucky Derby Handicapping Resources

Kentucky Derby Best Bets

Kentucky Derby Picks

If Things Go Well...

Exacta, Trifecta, Superfecta Picks

  • Exacta: 7-17
  • Trifecta: 7-17-14
  • Superfecta: 7-17-14-15

Projected Order of Finish

7 - Mandaloun
17 - Highly Motivated
14 - Essential Quality
15 - Rock Your World

147th Kentucky Derby Finish Prediction
PP Horse Trainer Jockey ML Odds
7 Mandaloun Brad Cox Florent Geroux 15/1
17 Highly Motivated Chad Brown Javier Castellano 10/1
14 Essential Quality Brad Cox Luis Saez 2/1
15 Rock Your World John Sadler Joel Rosario 5/1
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If All Hell Breaks Loose...

Exacta, Trifecta, Superfecta Picks:

  • Exacta: 8-6
  • Trifecta: 8-6-14
  • Superfecta: 8-6-14-20

8 - Medina Spirit
6 - O Besos
14 - Essential Quality
20 - Bourbonic

Projected Order of Finish

147th Kentucky Derby Finish Prediction
PP Horse Trainer Jockey ML Odds
8 Medina Spirit Bob Baffert John Velazquez 15/1
6 O Besos Greg Foley Marcelino Pedroza 20/1
14 Essential Quality Brad Cox Luis Saez 2/1
20 Bourbonic Todd Pletcher Kendrick Carmouche 30/1

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Kentucky Derby Betting Resources

  • Date: Saturday, May 1, 2021
  • Race: 12
  • Distance: 1 1/4 Miles
  • Surface: Dirt
  • Purse: $3,000,000
  • Post-Time: 6:57 p.m. ET
  • Where to Watch: NBC Sports
  • Location: Kentucky Derby - Louisville, Kentucky
  • Odds: Morning-Line
  • Picks: VegasInsider.com Experts

Handicapping the Field - 147th Kentucky Derby

Morning Line Odds are created by Churchill Downs oddsmaker Mike Battaglia.

(Kentucky Derby Career Record)

1) Known Agenda

  • Morning Line Odds: 6/1
  • Trainer: Todd Pletcher (2-55)
  • Jockey: Irad Ortiz, Jr. (0-4)

Connections have been high as really appeared to have turned the corner since blinkers were added two back. I know the rail can be a scary place in the Derby but with the new and improved starting gate there is a lot more room along the inside, and between us, the guy on his back is pretty good, plus he won saving ground in the Florida Derby. It’s not ideal but it’s not a nightmare. With all of that said, I’m not his biggest win. He can win but he will need to get a little faster and I question what he beat last out. Using underneath in exotics.

2) Like the King

  • Morning Line Odds: 50/1
  • Trainer: Wesley Ward (Debut)
  • Jockey: Drayden Van Dyke (0-2)

Jeff Ruby Steaks winner turned a clean enough trip behind a fast pace into a mild upset score, his second win over the synthetic surface at Turfway Park. His other victory came on the turf at Belterra Park. He’s winless in two dirt starts. Most amazing thing about him may be the fact that his trainer, for all he’s accomplished around the world, has never run a horse in this event. This wouldn’t have been the one I’d have chosen for my foray into the Derby, that’s for sure.

3) Brooklyn Strong

  • Morning Line Odds: 50/1
  • Trainer: Danny Velazquez (Debut)
  • Jockey: Umberto Rispoli (Debut)

We made it all the way to a week out before Derby Fever REALLY hit. This horse had his 2021 debut delayed a couple of times, has raced just once in four months and his best race came over a sloppy track. This has been a rush job if there has ever been a rush job. Hard pass.

4) Keepmeinmind

  • Morning Line Odds: 50/1
  • Trainer: Robertino Diodoro (Debut)
  • Jockey: David Cohen (Debut)

I thought he was poised for a big season after some solid juvenile efforts. I can forgive his Rebel, as he was supposed to return a month later in the twice-postponed Southwest but his last in the Blue Grass, despite the fact he was much closer to the lead than usual, was equally abysmal. He also gets an equipment change with the blinkers coming off. I never grasped doing something like that in a race like this. Hard to endorse off his 2021 form.

5) Sainthood

  • Morning Line Odds: 50/1
  • Trainer: Todd Pletcher (2-55)
  • Jockey: Corey Lanerie (0-2)

Didn’t have the best trip when second in the Jeff Ruby Steaks on synthetic and he does own a win on dirt at the Fair Grounds when he broke his maiden. That is his only win. He’s eligible for an entry level allowance contest and I’m not even sure I’d pick him in that spot so you can imagine what his chances are in here. Scariest part may be the fact that a few people have actually mentioned him as a live longshot. That’s what happens with horses off of bad trips.

6) O Besos

  • Morning Line Odds: 20/1
  • Trainer: Greg Foley (0-1)
  • Jockey: Marcelino Pedroza (Debut)

More often than and whether I agree with them or not, I understand why horses are “wise guy” horses in this race. I have to say I don’t get all the buzz around him. His two wins have come in sprints and it wasn’t like he was storming home when third last out in the Louisiana Derby. In fact, I think if they go around there again, he is finishing in the same position as he did. Pleasantly surprised at how low his morning line is and hope his fans pour it in. He’s not for me.

7) Mandaloun

  • Morning Line Odds: 15/1
  • Trainer: Brad Cox (Debut)
  • Jockey: Florent Geroux (0-4)

Unlike his next-door neighbor, this guy I get. Two months ago, he figured to be one of the favorites after a sharp tally in the Risen Star, but he was awful in the La. Derby and his price went up. Then, people started to watch him train and you realize he’s another horse that’s going to take money. I’m not in Kentucky but from the videos I’ve seen no horse has trained better. If you’re looking for an excuse for his last, you won’t get one from his connections because they don’t have one. I’ll offer up that though he raced at Fair Grounds all winter, the track last out was much quicker than the ones two and three back. And he was kept closer to a faster pace. You’d hope the rider will learn from his last effort and allow him to settle in here. I don’t love the six weeks between starts or the fact that a horse hasn’t won the Derby having finished off the board in his final prep in over 60 years, but I think he has a really big chance.

8) Medina Spirit

  • Morning Line Odds: 15/1
  • Trainer: Bob Baffert (6-33)
  • Jockey: John Velazquez (3-22)

The last one standing in the Baffert barn for Derby 147, I think he’ll be the main speed. I think that was the plan last time but Rock Your World broke running and with a purpose, so Johnny V rated him. Now he’s drawn inside his rival so I imagine the roles will be reversed. I’ve never been a fan of his and think he’ll have more trouble than most with the added distance, especially if he’s cutting the pace. Connections teamed up to win this last year and he’ll likely be a shorter price than he should be. Not for me.

9) Hot Rod Charlie

  • Morning Line Odds: 8/1
  • Trainer: Doug O’Neill (2-6)
  • Jockey: Flavien Prat (1-3)

They’ve run the La Derby at 1 3/16 miles for the past two years and both exactas were comprised of horses who essentially ran one-two around the track. Joel Rosario gave him a brilliant ride. This horse had NEVER been on the lead in six prior starts and was close to it just once. He won’t have the benefit of that brilliance and he likely won’t be on the lead. He has a bit of hang in him when he tries passing late, the last thing you want from a horse in any race, let alone the Derby. He doesn’t figure to be too far back, I would imagine no worse than third early, but he’ll also have to deal with runners late. I was on the fence but the closer we get to post time the more I’m against him.

10) Midnight Bourbon

  • Morning Line Odds: 20/1
  • Trainer: Steve Asmussen (0-21)
  • Jockey: Mike Smith (2-26)

Quickly took back in the La Derby after breaking best of all then just followed the winner around there, though he did try him in an early stretch before getting turned away. Of all the horses to come out of the bayou this year, he’s certainly been the most consistent, a constant through his seven starts as he’s never finished worse than third. He got a good post, should be with the first flight or just behind them and gets a big rider upgrade to one of the best to ever do it. I’m not sure he can win but I’ll use him in some of my vertical exotic wagers, like trifectas and superfectas.

11) Dynamic One

  • Morning Line Odds: 20/1
  • Trainer: Todd Pletcher (2-55
  • Jockey: Jose Ortiz (0-5)

Was looking to post an upset in the Wood Memorial and was 100 yards from doing so before stablemate Bourbonic ran by him to steal the spotlight. It was his best and fastest effort by far and certainly was a bit of an underachiever up until that race. He’s still eligible for an entry level allowance race and has lost ground/position in the stretch in four of his five starts. Would need to improve a good deal to be a major player. I’ll pass.

12) Helium

  • Morning Line Odds: 50/1
  • Trainer: Mark Casse (0-8)
  • Jockey: Julien Leparoux (0-12)

He’s only raced three times, with just one of those starts on dirt and around two turns. He’s also never been beyond 8.5 furlongs and hasn’t run in eight weeks. There are longshots, both live and impossible, in the Derby every year. He falls under the latter category for me.

13) Hidden Stash

  • Morning Line Odds: 50/1
  • Trainer: Vicki Oliver (Debut)
  • Jockey: Rafael Bejarano (0-10)

He’s one of just four horses in the field with a win over the course but if we’re being honest that’s about the only positive. He’s basically run the same figure in his last three races with varying degrees of success, or lack thereof. At the end of the day, he’s just too slow.

14) Essential Quality

  • Morning Line Odds: 2/1
  • Trainer: Brad Cox (Debut)
  • Jockey: Luis Saez (0-7)

He’s an undefeated, Breeders’ Cup Juvenile/two-year-old Eclipse champion. A healthy resume for any Derby but especially this year with some of the faster horses now on the sidelines and a lot of questions facing what’s left. He has to answer the distance question like the rest of them but that’s about it. He wins from just off the pace, from mid-pack, from far back. It’s hard to find something bad to say about him. Maybe the fact that he’s the favorite but that has nothing to do with him or what happens on the track. Only we care about that. He’s one of the most likely winners of the race and will be on all of my tickets.

15) Rock Your World

  • Morning Line Odds: 5/1
  • Trainer: John Sadler (0-4)
  • Jockey: Joel Rosario (1-9)

Stormed into the Derby picture with a monstrous effort in the Santa Anita Derby, taking them gate to wire in his first dirt start. He won his two prior starts on turf and travels more like a turf horse. It certainly didn’t matter last out. I would imagine he’ll switch roles with Medina Spirit and have to stalk him in here, but he’s done that successfully on turf and gets a huge rider upgrade to one of the best in the business, who just so happened to be aboard in his debut. He’s the only runner with a triple digit Beyer speed figure. His trainer has not had great success outside of SoCal, especially in big spots, but this guy is obviously incredibly talented. One of the ones for me. He’ll be on all my tickets.

16) King Fury

  • Morning Line Odds: 20/1
  • Trainer: Ken McPeek (0-6)
  • Jockey: Brian Hernandez, Jr. (0-2)

Came up with a big effort off the bench with a rail running move in the slop at Keeneland in the Lexington, his first start in close to five months. He’s run six times, all at 1 1/16 miles, so he has plenty of foundation BUT will be stretching out an extra furlong and a half. Only four horses in the field have won over the course – him, Essential Quality, Mandaloun and Hidden Stash – and he’s the only one to win beneath the twin spires twice. Was it the slop last out or is he getting good at the right time? If you’re looking for a live longshot, look no further.

17) Highly Motivated

  • Morning Line Odds: 10/1
  • Trainer: Chad Brown (0-5)
  • Jockey: Javier Castellano (0-14)

Another model of consistency as he’s never been off the board in five starts. He had a tough trip in the Gotham two back, his first start at a mile and in four months then was asked to set the pace for the first time in his career in the Blue Grass where he managed to hold Essential Quality at bay until the last handful of jumps. When he made the third start of his career/form cycle last year he ran a proverbial hole in the wind at Keeneland in a sprint stakes. If he improves from his second to third start this year like he did last year his rivals will have their hooves full. A must use in everything.

18) Super Stock

  • Morning Line Odds: 30/1
  • Trainer: Steve Asmussen (0-21)
  • Jockey: Ricardo Santana, Jr (0-6)

Was kept closer to the pace and got a great ride and trip to upset the Arkansas Derby most recently. That effort was so much better than anything else he’s produced that it is almost hard to believe. The fact that the horses he defeated aren’t coming back in here for a myriad of reasons, from health issues to lack of talent, bothers me but he’s going to be a big price so it’s not like you’re taking a shot on a horse at short odds. He’d have to take another pretty big step forward to win, but he could get a small piece. I’ll use him underneath in exotics.

19) Sour and Sandwich

  • Morning Line Odds: 30/1
  • Trainer: Mark Casse (0-8)
  • Jockey: Tyler Gaffalione (0-3)

Was part of a contested pace in the Florida Derby and dug in gamely to hold the place money. Now he’ll be on the chase from this draw, but I am curious to see how much of his speed the jock decides to use in the early going. I wasn’t a fan going in and I’m certainly not a fan now.

20) Bourbonic

  • Morning Line Odds: 30/1
  • Trainer: Todd Pletcher (2-55)
  • Jockey: Kendrick Carmouche (Debut)

You could have claimed him for $40K out of his maiden win in late December when blinkers were added. He’s won three of his four starts with the rogue’s badge, including posting the biggest upset in the history of the Wood Memorial at 72-1 when he passed all his rivals in the last quarter mile. Even though the pace last out was pedestrian it certainly would appear that he’d need a monumental pace collapse to have any chance in here. Not for me.

Who is the Big A?

VegasInsider.com Horse Racing expert Anthony Stabile provides his "Stabile's Seven" rankings throughout the Kentucky Derby prep trail.

Anthony “the Big A” Stabile can be heard regularly on the Horse Racing Radio Network from 3-6:00 p.m. ET on Wednesday and 3-7:00 p.m. ET Thursday and Friday.

Tune in on Sirius 219, XM 201 or streaming live at horseracingradio.net. He also is a contributor on NYRA-TV as the co-host of Talking Horses and a backup racetrack announcer. Follow him on Twitter @TheBigAStabile


  
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