Expert Predictions on Who Will Win the Kentucky Derby

The 2021 Kentucky Derby is set to get underway on Saturday, May 1st at Churchill Downs. This is a Grade 1 stakes race for three-year-old thoroughbreds, and it’s held annually in Louisville, Kentucky. This is a 1 1/4-mile race that is known in the United States as “The Fastest Two Minutes in Sports” as well as the “Run for the Roses”.

It is the first leg of the Triple Crown, which is followed by the Preakness Stakes and the Belmont Stakes. The Kentucky Derby has been run every year since 1875, making this the 147th running. The attendance at the event ranks first in North America and surpasses that of all the other stakes races, including the Breeders’ Cup.

Because of its popularity, the Kentucky Derby draws millions of fans and bettors around the world. I’m going to take a look at the wagering side of it and go through and give my predictions for this year’s race. I will give my Win, Place and Show picks for the horses to finish in 1st, 2nd and 3rd.  I will also give my exotic bets.

Note – I have picked three of the past nine Kentucky Derby Winners with American Pharaoh (5/2) in 2015, Orb (7/2) in 2013, and I’ll Have Another (12/1) in 2012 with my ‘Win’ selections.  

In 2017, I had Always Dreaming picked to finish 2nd and he won, so we cashed our place wager.  I also noted that I may regret not picking him to win.

In 2018, I hit the Exacta AND the Trifecta with Justify, Good Magic and Audible finishing in 1st, 2nd and 3rd.  I had a 6-7-11 Exacta Box and a 5-6-7-11 Trifecta Box.  A $2 Exacta Box cost $12 and paid $69.60, and a $2 Trifecta Box cost $24 and paid back $282.80.

2021 Kentucky Derby Betting: Win, Place, Show and Exotic Picks

Win: #1 Known Agenda (16/1)

Most bettors will be scared off by the No. 1 post Known Agenda has drawn, but not this bettor. No horse has won from the No. 1 post since Ferdinand in 1986. But in 2020, a new 20-stall starting gate was used that provides more room on the inside.

So basically rather than starting from the No. 1 post where it used to be, it’s like you’re coming out of the No. 3 post. There’s just more room for the inside horses to operate now. And with four 50-1 long shots in the 2 through 5 posts, plus slow starter O Besos in the 6th post, Known Agenda should get a perfectly fine trip and stalk the leaders that break from the outside.

Known Agenda is the best horse in the field in my opinion and can overcome the tough post draw. Since adding blinkers two races ago, he won his first race by 11 lengths with a 103 Equibase Speed Figure. He then won the Florida Derby one month later by coming from 2 1/2 lengths back on the final turn to win with a career best 112 Equibase Speed Figure, which is the best mark in the entire Kentucky Derby Field.

That type of closing speed is exactly what is needed to win the Kentucky Derby. And 2020 North American leading jockey Irad Ortiz Jr. knows him well after riding him for those two wins. He can save ground along the rail and win from a mid-pace position with the kind of closing kick he showed in the Florida Derby.

He is the son of two-time Horse of the Year Curlin, who finished third in the 2007 Kentucky Derby and has sired the most winners at this 10-furlong distance than any other stallion who has a starter in the 2021 Kentucky Derby.

Place: #19 Soup and Sandwich (30/1)

Naturally, since I’m picking Known Agenda to win, I can’t look past Soup and Sandwich at this ridiculous 30/1 price for a Place finish. He is a steadily improving three-year-old trained by Mark Casse.

Soup and Sandwich debuted at Gulfstream Park on January 28th and won by 7 1/4 lengths before being geared down late. He when won at Tampa Bay Downs before his initial stakes try at the Grade 1 Florida Derby.

There, Soup and Sandwich went off at 12/1 odds and held the lead on the backside before eventually getting passed by Known Agenda. Those two were way ahead of the rest of the field, and Soup and Sandwich finished three lengths ahead of multiple graded stakes winner Greatest Honour. He would have been a Derby favorite if he was in the field this week.

The 108 Equibase Speed Figure earned in the Florida Derby is actually the third-best figure in the field behind Known Agenda (112) and Essential Quality (109). I believe the wide draw from the No. 19 post actually benefits this colt.

He has the tactical speed to gain good position and the length of the stretch to make his way over so he’s not incredibly wide on the first turn. He should sit just off the pace for jockey Tyler Gaffalione and get the jump on some of the late runners. I expect a repeat of the Florida Derby where he is dueling with Known Agenda for the win.

Show: #14 Essential Quality (6/5)

It’s going to be tough to beat the favorite in Essential Quality. He is undefeated in five career starts and has the second-best Equibase Speed Figure (109) earned in his Blue Grass Stakes victory.

It didn’t come easy in the Blue Grass as it looked like he would never get by Highly Motivated, who led the from the start. But Essential Quality showed heart as the finish line neared and edged out Highly Motivated by a neck in a photo.

While that’s the heart of a champion, it also showed that Essential Quality is very beatable. And Known Agenda, Soup and Sandwich and Highly Motivated are all contenders to give him a run for his money.

4th: #15 Rock Your World (9/2)

Like Essential Quality, Rock Your World is undefeated in three career starts, all of which have come at Santa Anita. The latest was an impressive win at the Grade 1 Santa Anita Derby in which he led from the start and widened his lead in the last quarter-mile.

Clearly, Rock Your World does not need the lead as evidenced by his off-the-pace rallies in his first two starts. He has a physical presence about him that lets you know he’s a contender. And if he can keep improving in his fourth career race, it wouldn’t surprise me one bit if he won on Saturday.

That being said, his 103 Equibase Speed Figure in the Santa Anita Derby was a far cry from the three horses I have picked ahead of him in Known Agenda (112), Soup and Sandwich (108) and Essential Quality (109). He will need a big leap forward to challenge those three contenders.

5th: #17 Highly Motivated (16/1)

If you’re high on Essential Quality to contend in the Kentucky Derby, then you have to also expect Highly Motivated to find the board. He did everything right in the Blue Grass Stakes except come out on top. He finished a neck behind winner Essential Quality.

He improved with 87, 89, and 104 Equibase Speed Figures in his first three starts as a two-year-old.  Highly Motivated then took four months off before a disappointing third-place finish in the Grade 3 Gotham Stakes with a 102 figure.

I think that could have been due to rust, and Highly Motivated came back to post a career-best 108 figure in the Blue Grass Stakes. That number puts him right up there with other top contenders like Known Agenda, Essential Quality and Soup and Sandwich. That gives me reason to believe he can hang with those horses and be in the mix in the final furlong.

6th: #16 King Fury (SCR)

King Fury clearly likes Churchill Downs as he won his first and third races of his career here last year. He then bottomed out with 7th and 5th place finishes in his final two starts of 2020 before getting 4 1/2 months off.

Then he returned just three weeks ago in the Lexington Stakes and ran about as impressive a race as you will see. He closed from eighth of nine in the field to take the lead at the top of the stretch and opened up to win comfortably.

King Fury posted a 103 Equibase Speed Figure in the Lexington Stakes in the mud, and that matches the figure posted by Santa Anita Derby winner Rock Your World. Another closing kick like that and he could find the board.

It’s also worth noting that King Fury is the Son of Curlin, which is the same sire as Known Agenda. Curlin finished third in the 2007 Derby and has sired the most winners at 10 furlongs than any other stallion who has a starter in the 2021 Kentucky Derby. He has the bloodlines to get a mile and a quarter.

Note: King Fury has been scratched since this writing.  My next-favorite horse is the #6 O Besos (44/1).  So I’ll sub him in for the #16 in my exotics.

My Final 2021 Kentucky Derby Bets

Win Bet: $100 to Win on #1 (Costs $100)

Win, Place, Show Bet: $20 Across the Board on #19 (Costs $60)

Exacta Pick: $10 Exacta Key Box 1/6, 14, 15, 17, 19 (Costs $100)

Trifecta Pick: $2 Trifecta Key Box 1/6, 14, 15, 17, 19 (Costs $120)

Superfecta Pick: $.10 Superfecta Key Box 1/6, 14, 15, 17, 19 (Costs $24)

Note: A Key Box means I keyed the No. 1 horse Known Agenda.  That means you win your bet if Known Agenda comes in 1st or 2nd in the Exacta and also the 6, 14, 15, 17 or 19 comes in 1st or 2nd with him.  You will win your bet in the Trifecta if Known Agenda comes in 1st, 2nd or 3rd, and also two of 6, 14, 15, 17, 19 come in the top three with him.  You will win your Superfecta if Known Agenda comes in 1st, 2nd, 3rd or 4th and also 6, 14, 15, 17, 19 round out the top four places.

The wording for these exotic wagers at the betting window are as follows:

If you are new to the Kentucky Derby, then you might want to check out my betting guide for beginners.  This year’s complete odds are listed below.

Odds to Win the 2021 Kentucky Derby

Horse Odds
Essential Quality 6/5
Rock Your World 9/2
Hot Rod Charlie 7/1
Known Agenda 16/1
Highly Motivated 16/1
Midnight Bourbon 15/1
Medina Spirit 15/1
Soup and Sandwich 30/1
Bourbonic 33/1
Hidden Stash 39/1
Mandaloun 40/1
Sainthood 42/1
O Besos 44/1
Dynamic One 45/1
Super Stock 46/1
Helium 51/1
Keepmeinmind 53/1
Like the King 54/1
Brooklyn Strong 54/1
King Fury SCR

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